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Clorobiocin

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Chemical compound

Pharmaceutical compound

Clorobiocin
Clinical data

Other names	Chlorobiocin
ATC code	none
Identifiers
IUPAC name (3S,4R,5R,6S)-6-[(8-chloro-4-hydroxy-3-{[4-hydroxy-3-(3-methylbut-2-en-1-yl)benzene]amido}-2-oxo-2H-chromen-7-yl)oxy]-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl 5-methylpyrrole-2-carboxylate^[1]
CAS Number	39868-96-7^Y
PubChemCID	73622
ChemSpider	66286^N
ChEMBL	ChEMBL303984^N
Chemical and physical data
Formula	C₃₅H₃₇ClN₂O₁₁
Molar mass	697.13 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC1=CC=C(N1)C(=O)O[C@H]2[C@H]([C@@H](OC([C@@H]2OC)(C)C)OC3=C(C4=C(C=C3)C(=O)C(=C(O4)O)NC(=O)C5=CC(=C(C=C5)O)CC=C(C)C)Cl)O
InChI InChI=1S/C35H37ClN2O11/c1-16(2)7-9-18-15-19(10-13-22(18)39)31(42)38-25-26(40)20-11-14-23(24(36)28(20)47-33(25)44)46-34-27(41)29(30(45-6)35(4,5)49-34)48-32(43)21-12-8-17(3)37-21/h7-8,10-15,27,29-30,34,37,39,41,44H,9H2,1-6H3,(H,38,42)/t27-,29+,30-,34-/m1/s1^N Key:NOLDNICYUPLDOY-LFLQOBSNSA-N^N
^NY (what is this?) (verify)

Clorobiocin is anaminocoumarin antibacterial that inhibits the enzymeDNA gyrase.^[2]^[3]

^[1],http://www.drugbank.ca/drugs/DB03966.
^Pojer F, Wemakor E, Kammerer B, Chen H, Walsh CT, Li SM, Heide L (March 2003)."CloQ, a prenyltransferase involved in clorobiocin biosynthesis".Proceedings of the National Academy of Sciences of the United States of America.100 (5):2316–21.Bibcode:2003PNAS..100.2316P.doi:10.1073/pnas.0337708100.PMC 151338.PMID 12618544.
^Heide L (2009). "Genetic engineering of antibiotic biosynthesis for the generation of new aminocoumarins".Biotechnology Advances.27 (6):1006–1014.doi:10.1016/j.biotechadv.2009.05.017.PMID 19463934.

Antifolates
(inhibit bacterial
purine metabolism,
thereby inhibiting
DNA and RNA
synthesis)

Short-acting	Sulfaisodimidine Sulfamethizole Sulfadimidine (Sulfamethazine,Sulfadimerazine,Sulfadimezine) Sulfapyridine (Sulfasalazine) Sulfafurazole (Acetyl sulfisoxazole) Sulfanilamide Prontosil Sulfathiazole (Phthalylsulfathiazole,Succinylsulfathiazole) Sulfathiourea
Intermediate-acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole
Long-acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone
Other/ungrouped	Mafenide Sulfacetamide Sulfaclozine Sulfadicramide Sulfaguanidine Sulfametrole Sulfanitran

Combinations

Other DHPS inhibitors

Quinolones
(inhibit bacterial
topoisomerase
and/orDNA gyrase,
thereby inhibiting
DNA replication)

2nd generation	Ciprofloxacin^# Ofloxacin Enoxacin^‡ Fleroxacin^‡ Lomefloxacin^‡ Nadifloxacin^‡/Levonadifloxacin/Alalevonadifloxacin Norfloxacin^‡ Pefloxacin^‡ Rufloxacin^‡
3rd generation	Levofloxacin^# Balofloxacin^‡ Grepafloxacin^‡ Pazufloxacin^‡ Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin^‡
4th generation	Besifloxacin Delafloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin^# Clinafloxacin^† Garenoxacin^‡ Prulifloxacin^‡ Sitafloxacin^‡ Trovafloxacin^‡/Alatrofloxacin^‡
Veterinary	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin^‡