Showing metabocard for Valproic acid (HMDB0001877)

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enzymes (25) Show 25 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-02-24 11:11:14 UTC

Update Date

2023-02-21 17:15:54 UTC

HMDB ID

HMDB0001877

Secondary Accession Numbers

HMDB01877

Metabolite Identification

Common Name

Valproic acid

Description

Valproic acid (VPA) is considered to be a drug of first choice and one of the most frequently-prescribed antiepileptic drugs worldwide for the therapy of generalized and focal epilepsies, including special epileptic. It is a broad-spectrum antiepileptic drug and is usually well tolerated. Rarely, serious complications may occur in some patients, including hemorrhagic pancreatitis, coagulopathies, bone marrow suppression, VPA-induced hepatotoxicity and encephalopathy, but there is still a lack of knowledge about the incidence and occurrence of these special side effects. VPA has been approved for stabilization of manic episodes in patients with bipolar disorder. It is also used to treat migraine headaches and schizophrenia. As the use of VPA increases, the number of both accidental and intentional exposures increases. This is paralleled by more reports of VPA-induced toxicity. VPA is relatively contraindicated in pregnancy due to its teratogenicity. It is a known folate antagonist, which can cause neural tube defects. Thus, folic acid supplements may alleviate teratogenic problems. Women who become pregnant whilst taking valproate should be counselled as to its risks. VPA is an inhibitor of the enzyme histone deacetylase 1 (HDAC1). HDAC1 is needed for HIV to remain in infected cells. Patients treated with valproic acid in addition to highly active antiretroviral therapy (HAART) showed a median 75% reduction in latent HIV infection. VPA is believed to affect the function of the neurotransmitter GABA (as a GABA transaminase inhibitor) in the human brain. Valproic Acid dissociates to the valproate ion in the gastrointestinal tract. (PMID:18201150,17496767).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

MOL for HMDB0001877 (Valproic acid)

  Mrv1652305271900322D           10  9  0  0  0  0            999 V2000   -1.4289    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0   -0.7145   -0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0    0.0000    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0    0.7145   -0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0    1.4289    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0    0.0000   -1.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0    0.0000   -2.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0    0.7145   -1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0    2.1434   -0.2475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0    1.4289    0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0  2  1  1  0  0  0  0  2  3  1  0  0  0  0  3  4  1  0  0  0  0  4  8  1  0  0  0  0  4  5  1  0  0  0  0  5  9  1  0  0  0  0  5 10  2  0  0  0  0  6  7  1  0  0  0  0  6  8  1  0  0  0  0M  END

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3D MOL for HMDB0001877 (Valproic acid)

HMDB0001877     RDKit          3DValproic acid 26 25  0  0  0  0  0  0  0  0999 V2000    2.8499    0.8540   -1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0    1.3193    0.8024   -0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0    1.1139    0.0535    0.5130 C   0  0  0  0  0  0  0  0  0  0  0  0   -0.2394   -0.1274    1.0553 C   0  0  0  0  0  0  0  0  0  0  0  0   -1.2765   -0.8441    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0   -1.7223   -0.3553   -1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0   -2.2739    1.0578   -0.9997 C   0  0  0  0  0  0  0  0  0  0  0  0   -0.0697   -0.9172    2.3476 C   0  0  0  0  0  0  0  0  0  0  0  0   -0.4283   -0.4966    3.4548 O   0  0  0  0  0  0  0  0  0  0  0  0    0.5144   -2.1555    2.2455 O   0  0  0  0  0  0  0  0  0  0  0  0    3.0298    1.7250   -1.6600 H   0  0  0  0  0  0  0  0  0  0  0  0    3.3777    0.8543   -0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0    3.1522   -0.0566   -1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0    0.9293    0.3514   -1.6656 H   0  0  0  0  0  0  0  0  0  0  0  0    0.9117    1.8218   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0    1.6334   -0.9428    0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0    1.7187    0.5697    1.3330 H   0  0  0  0  0  0  0  0  0  0  0  0   -0.6515    0.8535    1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0   -0.9117   -1.9136    0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0   -2.2029   -1.0397    0.9168 H   0  0  0  0  0  0  0  0  0  0  0  0   -2.6654   -0.9810   -1.2601 H   0  0  0  0  0  0  0  0  0  0  0  0   -1.1123   -0.4796   -1.8891 H   0  0  0  0  0  0  0  0  0  0  0  0   -3.2482    1.0928   -0.4758 H   0  0  0  0  0  0  0  0  0  0  0  0   -1.5305    1.7497   -0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0   -2.4326    1.3395   -2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0    0.2147   -2.8160    1.5563 H   0  0  0  0  0  0  0  0  0  0  0  0  1  2  1  0  2  3  1  0  3  4  1  0  4  5  1  0  5  6  1  0  6  7  1  0  4  8  1  0  8  9  2  0  8 10  1  0  1 11  1  0  1 12  1  0  1 13  1  0  2 14  1  0  2 15  1  0  3 16  1  0  3 17  1  0  4 18  1  0  5 19  1  0  5 20  1  0  6 21  1  0  6 22  1  0  7 23  1  0  7 24  1  0  7 25  1  0 10 26  1  0M  END

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3D SDF for HMDB0001877 (Valproic acid)

  Mrv1652305271900322D           10  9  0  0  0  0            999 V2000   -1.4289    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0   -0.7145   -0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0    0.0000    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0    0.7145   -0.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0    1.4289    0.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0    0.0000   -1.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0    0.0000   -2.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0    0.7145   -1.0725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0    2.1434   -0.2475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0    1.4289    0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0  2  1  1  0  0  0  0  2  3  1  0  0  0  0  3  4  1  0  0  0  0  4  8  1  0  0  0  0  4  5  1  0  0  0  0  5  9  1  0  0  0  0  5 10  2  0  0  0  0  6  7  1  0  0  0  0  6  8  1  0  0  0  0M  END> <DATABASE_ID>HMDB0001877> <DATABASE_NAME>hmdb> <SMILES>CCCC(CCC)C(O)=O> <INCHI_IDENTIFIER>InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)> <INCHI_KEY>NIJJYAXOARWZEE-UHFFFAOYSA-N> <FORMULA>C8H16O2> <MOLECULAR_WEIGHT>144.2114> <EXACT_MASS>144.115029756> <JCHEM_ACCEPTOR_COUNT>2> <JCHEM_ATOM_COUNT>26> <JCHEM_AVERAGE_POLARIZABILITY>16.996878483662726> <JCHEM_BIOAVAILABILITY>1> <JCHEM_DONOR_COUNT>1> <JCHEM_FORMAL_CHARGE>0> <JCHEM_GHOSE_FILTER>0> <JCHEM_IUPAC>2-propylpentanoic acid> <ALOGPS_LOGP>2.54> <JCHEM_LOGP>2.7984510709999997> <ALOGPS_LOGS>-1.79> <JCHEM_MDDR_LIKE_RULE>0> <JCHEM_NUMBER_OF_RINGS>0> <JCHEM_PHYSIOLOGICAL_CHARGE>-1> <JCHEM_PKA_STRONGEST_ACIDIC>5.144389811177235> <JCHEM_POLAR_SURFACE_AREA>37.3> <JCHEM_REFRACTIVITY>40.2491> <JCHEM_ROTATABLE_BOND_COUNT>5> <JCHEM_RULE_OF_FIVE>1> <ALOGPS_SOLUBILITY>2.36e+00 g/l> <JCHEM_TRADITIONAL_IUPAC>valproic acid> <JCHEM_VEBER_RULE>1$$$$

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3D-SDF for HMDB0001877 (Valproic acid)

HMDB0001877     RDKit          3DValproic acid 26 25  0  0  0  0  0  0  0  0999 V2000    2.8499    0.8540   -1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0    1.3193    0.8024   -0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0    1.1139    0.0535    0.5130 C   0  0  0  0  0  0  0  0  0  0  0  0   -0.2394   -0.1274    1.0553 C   0  0  0  0  0  0  0  0  0  0  0  0   -1.2765   -0.8441    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0   -1.7223   -0.3553   -1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0   -2.2739    1.0578   -0.9997 C   0  0  0  0  0  0  0  0  0  0  0  0   -0.0697   -0.9172    2.3476 C   0  0  0  0  0  0  0  0  0  0  0  0   -0.4283   -0.4966    3.4548 O   0  0  0  0  0  0  0  0  0  0  0  0    0.5144   -2.1555    2.2455 O   0  0  0  0  0  0  0  0  0  0  0  0    3.0298    1.7250   -1.6600 H   0  0  0  0  0  0  0  0  0  0  0  0    3.3777    0.8543   -0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0    3.1522   -0.0566   -1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0    0.9293    0.3514   -1.6656 H   0  0  0  0  0  0  0  0  0  0  0  0    0.9117    1.8218   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0    1.6334   -0.9428    0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0    1.7187    0.5697    1.3330 H   0  0  0  0  0  0  0  0  0  0  0  0   -0.6515    0.8535    1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0   -0.9117   -1.9136    0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0   -2.2029   -1.0397    0.9168 H   0  0  0  0  0  0  0  0  0  0  0  0   -2.6654   -0.9810   -1.2601 H   0  0  0  0  0  0  0  0  0  0  0  0   -1.1123   -0.4796   -1.8891 H   0  0  0  0  0  0  0  0  0  0  0  0   -3.2482    1.0928   -0.4758 H   0  0  0  0  0  0  0  0  0  0  0  0   -1.5305    1.7497   -0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0   -2.4326    1.3395   -2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0    0.2147   -2.8160    1.5563 H   0  0  0  0  0  0  0  0  0  0  0  0  1  2  1  0  2  3  1  0  3  4  1  0  4  5  1  0  5  6  1  0  6  7  1  0  4  8  1  0  8  9  2  0  8 10  1  0  1 11  1  0  1 12  1  0  1 13  1  0  2 14  1  0  2 15  1  0  3 16  1  0  3 17  1  0  4 18  1  0  5 19  1  0  5 20  1  0  6 21  1  0  6 22  1  0  7 23  1  0  7 24  1  0  7 25  1  0 10 26  1  0M  END

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PDB for HMDB0001877 (Valproic acid)

HEADER    PROTEIN                                 27-MAY-19   NONETITLE     NULL                                                        COMPND    NULL                                                        SOURCE    NULL                                                        KEYWDS    NULL                                                        EXPDTA    NULL                                                        AUTHOR    Marvin                                                      REVDAT   1   27-MAY-19         0                                  HETATM    1  C   UNK     0      -2.667   0.308   0.000  0.00  0.00           C+0HETATM    2  C   UNK     0      -1.334  -0.462   0.000  0.00  0.00           C+0HETATM    3  C   UNK     0       0.000   0.308   0.000  0.00  0.00           C+0HETATM    4  C   UNK     0       1.334  -0.462   0.000  0.00  0.00           C+0HETATM    5  C   UNK     0       2.667   0.308   0.000  0.00  0.00           C+0HETATM    6  C   UNK     0       0.000  -2.772   0.000  0.00  0.00           C+0HETATM    7  C   UNK     0       0.000  -4.312   0.000  0.00  0.00           C+0HETATM    8  C   UNK     0       1.334  -2.002   0.000  0.00  0.00           C+0HETATM    9  O   UNK     0       4.001  -0.462   0.000  0.00  0.00           O+0HETATM   10  O   UNK     0       2.667   1.848   0.000  0.00  0.00           O+0CONECT    1    2                                                            CONECT    2    1    3                                                       CONECT    3    2    4                                                       CONECT    4    3    8    5                                                  CONECT    5    4    9   10                                                  CONECT    6    7    8                                                       CONECT    7    6                                                            CONECT    8    4    6                                                       CONECT    9    5                                                            CONECT   10    5                                                            MASTER        0    0    0    0    0    0    0    0   10    0   18    0END

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3D PDB for HMDB0001877 (Valproic acid)

COMPND    HMDB0001877HETATM    1  C1  UNL     1       2.850   0.854  -1.020  1.00  0.00           C  HETATM    2  C2  UNL     1       1.319   0.802  -0.745  1.00  0.00           C  HETATM    3  C3  UNL     1       1.114   0.054   0.513  1.00  0.00           C  HETATM    4  C4  UNL     1      -0.239  -0.127   1.055  1.00  0.00           C  HETATM    5  C5  UNL     1      -1.277  -0.844   0.294  1.00  0.00           C  HETATM    6  C6  UNL     1      -1.722  -0.355  -1.017  1.00  0.00           C  HETATM    7  C7  UNL     1      -2.274   1.058  -1.000  1.00  0.00           C  HETATM    8  C8  UNL     1      -0.070  -0.917   2.348  1.00  0.00           C  HETATM    9  O1  UNL     1      -0.428  -0.497   3.455  1.00  0.00           O  HETATM   10  O2  UNL     1       0.514  -2.156   2.246  1.00  0.00           O  HETATM   11  H1  UNL     1       3.030   1.725  -1.660  1.00  0.00           H  HETATM   12  H2  UNL     1       3.378   0.854  -0.066  1.00  0.00           H  HETATM   13  H3  UNL     1       3.152  -0.057  -1.579  1.00  0.00           H  HETATM   14  H4  UNL     1       0.929   0.351  -1.666  1.00  0.00           H  HETATM   15  H5  UNL     1       0.912   1.822  -0.665  1.00  0.00           H  HETATM   16  H6  UNL     1       1.633  -0.943   0.414  1.00  0.00           H  HETATM   17  H7  UNL     1       1.719   0.570   1.333  1.00  0.00           H  HETATM   18  H8  UNL     1      -0.652   0.853   1.450  1.00  0.00           H  HETATM   19  H9  UNL     1      -0.912  -1.914   0.115  1.00  0.00           H  HETATM   20  H10 UNL     1      -2.203  -1.040   0.917  1.00  0.00           H  HETATM   21  H11 UNL     1      -2.665  -0.981  -1.260  1.00  0.00           H  HETATM   22  H12 UNL     1      -1.112  -0.480  -1.889  1.00  0.00           H  HETATM   23  H13 UNL     1      -3.248   1.093  -0.476  1.00  0.00           H  HETATM   24  H14 UNL     1      -1.530   1.750  -0.585  1.00  0.00           H  HETATM   25  H15 UNL     1      -2.433   1.340  -2.067  1.00  0.00           H  HETATM   26  H16 UNL     1       0.215  -2.816   1.556  1.00  0.00           H  CONECT    1    2   11   12   13CONECT    2    3   14   15CONECT    3    4   16   17CONECT    4    5    8   18CONECT    5    6   19   20CONECT    6    7   21   22CONECT    7   23   24   25CONECT    8    9    9   10CONECT   10   26END

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SMILES for HMDB0001877 (Valproic acid)

CCCC(CCC)C(O)=O

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INCHI for HMDB0001877 (Valproic acid)

InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)

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Structure for HMDB0001877 (Valproic acid)

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3D Structure for HMDB0001877 (Valproic acid)

HMDB0001877     RDKit          3DValproic acid 26 25  0  0  0  0  0  0  0  0999 V2000    2.8499    0.8540   -1.0200 C   0  0  0  0  0  0  0  0  0  0  0  0    1.3193    0.8024   -0.7455 C   0  0  0  0  0  0  0  0  0  0  0  0    1.1139    0.0535    0.5130 C   0  0  0  0  0  0  0  0  0  0  0  0   -0.2394   -0.1274    1.0553 C   0  0  0  0  0  0  0  0  0  0  0  0   -1.2765   -0.8441    0.2942 C   0  0  0  0  0  0  0  0  0  0  0  0   -1.7223   -0.3553   -1.0171 C   0  0  0  0  0  0  0  0  0  0  0  0   -2.2739    1.0578   -0.9997 C   0  0  0  0  0  0  0  0  0  0  0  0   -0.0697   -0.9172    2.3476 C   0  0  0  0  0  0  0  0  0  0  0  0   -0.4283   -0.4966    3.4548 O   0  0  0  0  0  0  0  0  0  0  0  0    0.5144   -2.1555    2.2455 O   0  0  0  0  0  0  0  0  0  0  0  0    3.0298    1.7250   -1.6600 H   0  0  0  0  0  0  0  0  0  0  0  0    3.3777    0.8543   -0.0664 H   0  0  0  0  0  0  0  0  0  0  0  0    3.1522   -0.0566   -1.5789 H   0  0  0  0  0  0  0  0  0  0  0  0    0.9293    0.3514   -1.6656 H   0  0  0  0  0  0  0  0  0  0  0  0    0.9117    1.8218   -0.6652 H   0  0  0  0  0  0  0  0  0  0  0  0    1.6334   -0.9428    0.4140 H   0  0  0  0  0  0  0  0  0  0  0  0    1.7187    0.5697    1.3330 H   0  0  0  0  0  0  0  0  0  0  0  0   -0.6515    0.8535    1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0   -0.9117   -1.9136    0.1146 H   0  0  0  0  0  0  0  0  0  0  0  0   -2.2029   -1.0397    0.9168 H   0  0  0  0  0  0  0  0  0  0  0  0   -2.6654   -0.9810   -1.2601 H   0  0  0  0  0  0  0  0  0  0  0  0   -1.1123   -0.4796   -1.8891 H   0  0  0  0  0  0  0  0  0  0  0  0   -3.2482    1.0928   -0.4758 H   0  0  0  0  0  0  0  0  0  0  0  0   -1.5305    1.7497   -0.5851 H   0  0  0  0  0  0  0  0  0  0  0  0   -2.4326    1.3395   -2.0665 H   0  0  0  0  0  0  0  0  0  0  0  0    0.2147   -2.8160    1.5563 H   0  0  0  0  0  0  0  0  0  0  0  0  1  2  1  0  2  3  1  0  3  4  1  0  4  5  1  0  5  6  1  0  6  7  1  0  4  8  1  0  8  9  2  0  8 10  1  0  1 11  1  0  1 12  1  0  1 13  1  0  2 14  1  0  2 15  1  0  3 16  1  0  3 17  1  0  4 18  1  0  5 19  1  0  5 20  1  0  6 21  1  0  6 22  1  0  7 23  1  0  7 24  1  0  7 25  1  0 10 26  1  0M  END

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Synonyms

Value	Source
2-N-Propyl-N-valeric acid	ChEBI
2-PROPYL-pentanoIC ACID	ChEBI
2-Propylpentanoic acid	ChEBI
2-Propylvaleric acid	ChEBI
4-Heptanecarboxylic acid	ChEBI
Acide valproique	ChEBI
Acido valproico	ChEBI
Acidum valproicum	ChEBI
Depakene	ChEBI
Di-N-propylacetic acid	ChEBI
Di-N-propylessigsaeure	ChEBI
Dipropylacetic acid	ChEBI
DPA	ChEBI
N-DPA	ChEBI
Valproinsaeure	ChEBI
VPA	ChEBI
2-N-Propyl-N-valerate	Generator
2-PROPYL-pentanoate	Generator
2-Propylpentanoate	Generator
2-Propylvalerate	Generator
4-Heptanecarboxylate	Generator
Di-N-propylacetate	Generator
Dipropylacetate	Generator
Valproate	Generator
(N-C3H7)2chcooh	HMDB
(S)-2-Propyl-4-pentanoate	HMDB
(S)-2-Propyl-4-pentanoic acid	HMDB
Alti-valproic	HMDB
Apo-divalproex	HMDB
Apo-valproic	HMDB
Apo-valproic syrup	HMDB
Avugane	HMDB
Baceca	HMDB
Convulex	HMDB
Delepsine	HMDB
Depakin	HMDB
Depakin chrono	HMDB
Depakine	HMDB
Depakine chrono	HMDB
Deproic	HMDB
Di-N-propylessigsaure	HMDB
Divalproex	HMDB
DOM-divalproex	HMDB
Dom-valproate	HMDB
DOM-valproic	HMDB
Dom-valproic acid	HMDB
DOM-valproic acid e.c.	HMDB
Dom-valproic acid syrup	HMDB
Epiject i.v.	HMDB
Epilex	HMDB
Epilim	HMDB
Epival	HMDB
Epival er	HMDB
Ergenyl	HMDB
Gen-divalproex	HMDB
Kyselina 2-propylvalerova	HMDB
Med valproic	HMDB
Mylproin	HMDB
Myproate	HMDB
Myproic acid	HMDB
N-Dipropylacetic acid	HMDB
Novo-divalproex	HMDB
Novo-valproic	HMDB
Novo-valproic - ecc	HMDB
Novo-valproic soft gel cap	HMDB
Nu-valproic	HMDB
PEAC	HMDB
Penta-valproic	HMDB
PHL-Valproate	HMDB
PHL-Valproic acid	HMDB
PHL-Valproic acid e.c.	HMDB
PMS-Divalproex	HMDB
PMS-Valproate	HMDB
PMS-Valproic acid	HMDB
PMS-Valproic acid e.c.	HMDB
Propylvaleric acid	HMDB
Ratio-valproic - ecc	HMDB
S(-)-4-En-valproate	HMDB
S(-)-4-En-valproic acid	HMDB
S-2-N-Propyl-4-pentenoate	HMDB
S-2-N-Propyl-4-pentenoic acid	HMDB
Sandoz valproic	HMDB
Savicol	HMDB
Sprinkle	HMDB
Valcote	HMDB
Valparin	HMDB
Valproic acid usp	HMDB
Dipropyl acetate	HMDB
Valproate, sodium	HMDB
Calcium, valproate	HMDB
Convulsofin	HMDB
Semisodium valproate	HMDB
Sodium valproate	HMDB
Valproate calcium	HMDB
Valproate, calcium	HMDB
Valproic acid, sodium salt (2:1)	HMDB
Acetate, dipropyl	HMDB
Depakote	HMDB
Divalproex sodium	HMDB
Magnesium valproate	HMDB
Sodium, divalproex	HMDB
Sodium, valproate	HMDB
Vupral	HMDB
2 Propylpentanoic acid	HMDB
Acid, propylisopropylacetic	HMDB
Acid, valproic	HMDB
Calcium valproate	HMDB
Propylisopropylacetic acid	HMDB
Valproate sodium	HMDB
Valproate, magnesium	HMDB
Valproate, semisodium	HMDB

Chemical Formula

C₈H₁₆O₂

Average Molecular Weight

144.2114

Monoisotopic Molecular Weight

144.115029756

IUPAC Name

2-propylpentanoic acid

Traditional Name

valproic acid

CAS Registry Number

99-66-1

SMILES

CCCC(CCC)C(O)=O

InChI Identifier

InChI=1S/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10)

InChI Key

NIJJYAXOARWZEE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-branched fatty acids

Alternative Parents

Substituents

Methyl-branched fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

branched-chain fatty acid (CHEBI:39867)
branched-chain saturated fatty acid (CHEBI:39867)
Branched fatty acids (LMFA01020291)

Ontology

Physiological effect

Health effect

Circulatory system disorder

Blood and lymphatic system disorder

Leukocytic disorder

Leukemia (HMDB:HMDB0001877)
Leukemia (HMDB:HMDB0001877)

Hyperammonemia (HMDB:HMDB0001877)

Vascular disorder

Hypotension (HMDB:HMDB0001877)

Nervous system disorder

Central nervous system disorder

Spina bifida (HMDB:HMDB0001877)

Psychiatric disorder

Mood disorder

Major depressive disorder (HMDB:HMDB0001877)

Coma (HMDB:HMDB0001877)

Observation

Renal system and urinary system

Renal disorder

Renal failure (HMDB:HMDB0001877)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID:15954179)

Cellular substructure

Organelle

Adiposome (HMDB:HMDB0001877)

Organ

Brain (HMDB:HMDB0001877)
Liver (HMDB:HMDB0001877)

Excreta

Biofluid or Excreta

Urine (HMDB:HMDB0001877)

Route of exposure

Parenteral

Inhalation (HMDB:HMDB0001877)

Enteral

Ingestion (HMDB:HMDB0001877)
Gastrointestinal (HMDB:HMDB0001877)

Source

Exogenous

Exogenous (HMDB:HMDB0001877)

Food

Food (HMDB:HMDB0001877)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB:HMDB0001877)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB:HMDB0001877)
Valproic Acid Metabolism Pathway (PathBank:SMP0000635)

Lipid metabolism pathway (HMDB:HMDB0001877)

Cellular process

Cell signaling (HMDB:HMDB0001877)

Biochemical process

Lipid transport (HMDB:HMDB0001877)

Role

Industrial application

Pharmaceutical industry

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Anticonvulsant (HMDB:HMDB0001877)
Anticonvulsant (HMDB:HMDB0001877)

Fluid processing agent

Surfactant

Surfactant (HMDB:HMDB0001877)

GABA agent (HMDB:HMDB0001877)
Neuroprotective agent (HMDB:HMDB0001877)

Biological role

Teratogenic agent (HMDB:HMDB0001877)
Energy source (HMDB:HMDB0001877)

Modulator

Inhibitor

EC 3.5.1.98 (histone deacetylase) inhibitor (HMDB:HMDB0001877)

Indirect biological role

Metabotoxin

Teratogen (HMDB:HMDB0001877)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	222 °C	Not Available
Water Solubility	2 mg/mL at 20 °C	Not Available
LogP	2.75	SANGSTER (1993)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.36 g/L	ALOGPS
logP	2.54	ALOGPS
logP	2.8	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	5.14	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	40.25 m³·mol⁻¹	ChemAxon
Polarizability	17 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	134.011	31661259
DarkChem	[M-H]-	130.509	31661259
AllCCS	[M+H]+	136.652	32859911
AllCCS	[M-H]-	136.411	32859911
DeepCCS	[M+H]+	137.545	30932474
DeepCCS	[M-H]-	134.659	30932474
DeepCCS	[M-2H]-	171.439	30932474
DeepCCS	[M+Na]+	146.349	30932474
AllCCS	[M+H]+	136.7	32859911
AllCCS	[M+H-H2O]+	132.6	32859911
AllCCS	[M+NH4]+	140.5	32859911
AllCCS	[M+Na]+	141.6	32859911
AllCCS	[M-H]-	136.4	32859911
AllCCS	[M+Na-2H]-	138.8	32859911
AllCCS	[M+HCOO]-	141.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Valproic acid	CCCC(CCC)C(O)=O	1906.7	Standard polar	33892256
Valproic acid	CCCC(CCC)C(O)=O	1083.8	Standard non polar	33892256
Valproic acid	CCCC(CCC)C(O)=O	1110.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Valproic acid,1TMS,isomer #1	CCCC(CCC)C(=O)O[Si](C)(C)C	1148.9	Semi standard non polar	33892256
Valproic acid,1TBDMS,isomer #1	CCCC(CCC)C(=O)O[Si](C)(C)C(C)(C)C	1373.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-004m-9300000000-e66da5fefd079f7426a4	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00b9-9100000000-7bb11c5d52ffa09851f8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Valproic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0fk9-9300000000-1a0314ea63d5a3c9bba1	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-0udi-2900000000-156413e81733a6236c1f	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-0f6y-2900000000-a769cafb885b78532cac	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-0gbj-7900000000-46a522b9a26459334f5a	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-0006-0900000000-39a45d4e3201082d9d89	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0002-9000000000-4ddd957d8c8dc2b1de03	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-0006-0900000000-6ba582ae102c4721034d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0006-0900000000-58d9ba88010f1b370c58	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0006-3900000000-2d1032d7e8ac58235b4f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0a4j-9000000000-0d39870bc4521a42c50a	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-00di-9000000000-3c4e21b69b8877d6df3e	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid LC-ESI-QQ , negative-QTOF	splash10-0006-0900000000-39a45d4e3201082d9d89	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid LC-ESI-QQ , negative-QTOF	splash10-0002-9000000000-4ddd957d8c8dc2b1de03	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid LC-ESI-QQ , negative-QTOF	splash10-0006-0900000000-6ba582ae102c4721034d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid LC-ESI-QQ , negative-QTOF	splash10-0006-0900000000-58d9ba88010f1b370c58	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid LC-ESI-QQ , negative-QTOF	splash10-0006-3900000000-2d1032d7e8ac58235b4f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid LC-ESI-QQ , negative-QTOF	splash10-0a4j-9000000000-0d39870bc4521a42c50a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid LC-ESI-QQ , negative-QTOF	splash10-00di-9000000000-3c4e21b69b8877d6df3e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid Linear Ion Trap , negative-QTOF	splash10-0006-0900000000-5b83f0d6c36f8249285a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Valproic acid 20V, Negative-QTOF	splash10-0006-0900000000-51a760d50a87d131ad67	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid 10V, Positive-QTOF	splash10-0002-3900000000-be0e79e3b65dad2e2d08	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid 20V, Positive-QTOF	splash10-0005-9500000000-37d8981251a94cfd51e3	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid 40V, Positive-QTOF	splash10-0006-9000000000-b63be8686bbf9a96b2ba	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid 10V, Negative-QTOF	splash10-0006-3900000000-25f23d80c7431c074a74	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid 20V, Negative-QTOF	splash10-0005-9500000000-144b6cc9fea5bae4f269	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Valproic acid 40V, Negative-QTOF	splash10-052e-9100000000-eb5e97329782125f6615	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O,experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H,¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O,experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood

Tissue Locations

Brain
Liver

Pathways

Name	SMPDB/PathBank	KEGG
Valproic Acid Metabolism Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	208.0 (3.5-416.0) uM	Adult (>18 years old)	Both	Normal	15954179	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00313

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022722

KNApSAcK ID

Not Available

Chemspider ID

3009

KEGG Compound ID

C07185

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Valproic_Acid

METLIN ID

2986

PubChem Compound

3121

PDB ID

Not Available

ChEBI ID

39867

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Nemeroff CB: The role of GABA in the pathophysiology and treatment of anxiety disorders. Psychopharmacol Bull. 2003;37(4):133-46. [PubMed:15131523]
Bell EC, Willson MC, Wilman AH, Dave S, Silverstone PH: Differential effects of chronic lithium and valproate on brain activation in healthy volunteers. Hum Psychopharmacol. 2005 Aug;20(6):415-24. [PubMed:16106488]
Sztajnkrycer MD: Valproic acid toxicity: overview and management. J Toxicol Clin Toxicol. 2002;40(6):789-801. [PubMed:12475192]
Seyfert S, Bernarding J, Braun J: Volume-selective 1H MR spectroscopy for in vivo detection of valproate in patients with epilepsy. Neuroradiology. 2003 May;45(5):295-9. Epub 2003 Mar 27. [PubMed:12669157]
Eyal S, Lamb JG, Smith-Yockman M, Yagen B, Fibach E, Altschuler Y, White HS, Bialer M: The antiepileptic and anticancer agent, valproic acid, induces P-glycoprotein in human tumour cell lines and in rat liver. Br J Pharmacol. 2006 Oct;149(3):250-60. Epub 2006 Aug 7. [PubMed:16894351]
Loscher W: Basic pharmacology of valproate: a review after 35 years of clinical use for the treatment of epilepsy. CNS Drugs. 2002;16(10):669-94. [PubMed:12269861]
Huang YL, Hong HS, Wang ZW, Kuo TT: Fatal sodium valproate-induced hypersensitivity syndrome with lichenoid dermatitis and fulminant hepatitis. J Am Acad Dermatol. 2003 Aug;49(2):316-9. [PubMed:12894087]
Anderson GD, Temkin NR, Chandler WL, Winn HR: Effect of valproate on hemostatic function in patients with traumatic brain injury. Epilepsy Res. 2003 Dec;57(2-3):111-9. [PubMed:15013052]
Ho PC, Abbott FS, Zanger UM, Chang TK: Influence of CYP2C9 genotypes on the formation of a hepatotoxic metabolite of valproic acid in human liver microsomes. Pharmacogenomics J. 2003;3(6):335-42. [PubMed:14597963]
Gerstner T, Bell N, Konig S: Oral valproic acid for epilepsy--long-term experience in therapy and side effects. Expert Opin Pharmacother. 2008 Feb;9(2):285-92. doi: 10.1517/14656566.9.2.285 . [PubMed:18201150]
Russell S: Carnitine as an antidote for acute valproate toxicity in children. Curr Opin Pediatr. 2007 Apr;19(2):206-10. [PubMed:17496767]

Only showing the first 10 proteins. There are25 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1.Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

Enzyme Details

2.Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

Enzyme Details

3.Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

Enzyme Details

4.Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

Enzyme Details

5.Cytochrome P450 3A43

General function:: Involved in monooxygenase activity
Specific function:: Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name:: CYP3A43
Uniprot ID:: Q9HB55
Molecular weight:: 57756.285

Enzyme Details

6.Cytochrome P450 1B1

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.Participates in the metabolism of an as-yet-unknown biologically active molecule that is a participant in eye development.
Gene Name:: CYP1B1
Uniprot ID:: Q16678
Molecular weight:: 60845.33

Enzyme Details

7.Cytochrome P450 2C18

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:: CYP2C18
Uniprot ID:: P33260
Molecular weight:: 55710.075

Enzyme Details

8.Cytochrome P450 2F1

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: May be involved in the metabolism of various pneumotoxicants including naphthalene. Is able to dealkylate ethoxycoumarin, propoxycoumarin, and pentoxyresorufin but possesses no activity toward ethoxyresorufin and only trace dearylation activity toward benzyloxyresorufin. Bioactivates 3-methylindole (3MI) by dehydrogenation to the putative electrophile 3-methylene-indolenine.
Gene Name:: CYP2F1
Uniprot ID:: P24903
Molecular weight:: 55500.64

Enzyme Details

9.Cytochrome P450 4X1

General function:: Involved in monooxygenase activity
Specific function:: Not Available
Gene Name:: CYP4X1
Uniprot ID:: Q8N118
Molecular weight:: 58874.62

Enzyme Details

10.Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

Only showing the first 10 proteins. There are25 proteins in total.

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Showing metabocard for Valproic acid (HMDB0001877)

MOL for HMDB0001877 (Valproic acid)

3D MOL for HMDB0001877 (Valproic acid)

3D SDF for HMDB0001877 (Valproic acid)

3D-SDF for HMDB0001877 (Valproic acid)

PDB for HMDB0001877 (Valproic acid)

3D PDB for HMDB0001877 (Valproic acid)

SMILES for HMDB0001877 (Valproic acid)

INCHI for HMDB0001877 (Valproic acid)

Structure for HMDB0001877 (Valproic acid)

3D Structure for HMDB0001877 (Valproic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes