(3S,4R,5R,6S)-6-({8-chloro-4-hydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamido]-2-oxo-2H-chromen-7-yl}oxy)-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl 5-methyl-1H-pyrrole-2-carboxylate

• ChemBase ID: 3597
• Molecular Formular: C35H37ClN2O11
• Molecular Mass: 697.12808
• Monoisotopic Mass: 696.20858769
• SMILES: CO[C@H]1[C@H](OC(=O)c2ccc(C)[nH]2)[C@@H](O)[C@H](Oc2ccc3c(O)c(NC(=O)c4ccc(O)c(CC=C(C)C)c4)c(=O)oc3c2Cl)OC1(C)C
• Canonical SMILES: CO[C@H]1[C@H](OC(=O)c2ccc([nH]2)C)[C@@H](O)[C@@H](OC1(C)C)Oc1ccc2c(c1Cl)oc(=O)c(c2O)NC(=O)c1ccc(c(c1)CC=C(C)C)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/h7-8,10-15,27,29-30,34,37,39-41H,9H2,1-6H3,(H,38,42)/t27-,29-,30+,34-/m1/s1
• InChIKey: FJAQNRBDVKIIKK-LOHKCFAQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R,5R,6S)-6-({8-chloro-4-hydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamido]-2-oxo-2H-chromen-7-yl}oxy)-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl 5-methyl-1H-pyrrole-2-carboxylate
• IUPAC Traditional name: (3S,4R,5R,6S)-6-({8-chloro-4-hydroxy-3-[4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamido]-2-oxochromen-7-yl}oxy)-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl 5-methyl-1H-pyrrole-2-carboxylate
• Synonyms: Chlorobiocin; Clorobiocin

Database IDs

• CAS Number: 39868-96-7
• PubChem SID: 46505267; 160967035
• PubChem CID: 46936849; 54715130

CALCULATED PROPERTIES

JChem

• Acid pKa: 6.5064406
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 4.900789
• LogD (pH = 7.4): 3.9501157
• Log P: 4.941601
• Molar Refractivity: 179.7876 cm^3
• Polarizability: 68.710976 Å^3
• Polar Surface Area: 185.87 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 5.0
• LOG S: -5.33
• Solubility (Water): 3.28e-03 g/l

DETAILS

DrugBank - DB03966

• Drug Groups: experimental
• Description: Clorobiocin is an aminocoumarin antibiotic, similar to novobiocin and coumermycin A1.
• Affected Organisms: Enteric bacteria and other eubacteria
• References: Tsai FT, Singh OM, Skarzynski T, Wonacott AJ, Weston S, Tucker A, Pauptit RA, Breeze AL, Poyser JP, O'Brien R, Ladbury JE, Wigley DB: The high-resolution crystal structure of a 24-kDa gyrase B fragment from E. coli complexed with one of the most potent coumarin inhibitors, clorobiocin. Proteins. 1997 May;28(1):41-52. [Pubmed] ; Cejka K, Holubova I, Hubacek J: Curing effect of clorobiocin on Escherichia coli plasmids. Mol Gen Genet. 1982;186(1):153-5. [Pubmed]

REFERENCES

• Tsai FT, Singh OM, Skarzynski T, Wonacott AJ, Weston S, Tucker A, Pauptit RA, Breeze AL, Poyser JP, O'Brien R, Ladbury JE, Wigley DB: The high-resolution crystal structure of a 24-kDa gyrase B fragment from E. coli complexed with one of the most potent coumarin inhibitors, clorobiocin. Proteins. 1997 May;28(1):41-52. Pubmed
• Cejka K, Holubova I, Hubacek J: Curing effect of clorobiocin on Escherichia coli plasmids. Mol Gen Genet. 1982;186(1):153-5. Pubmed