Details of the Drug

General Information of Drug (ID: DMD5FIU)

Drug Name

Clorobiocin

Synonyms

Clorobiocin; Chlorobiocin; Antibiotic RP 18,631; NSC 227186; RP 18631; 18631 RP; 39868-96-7; CHEMBL303984; 1H-Pyrrole-2-carboxylic acid, 5-methyl-, 3'-ester with N-(8-chloro-7-((6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lyxo-hexopyranosyl)oxy)-4-hydroxy-2-oxo-2H-1-benzopyran-3-yl)-4-hydroxy-3-(3-methyl-2-butenyl)benzamide; [(3R,4S,5R,6S)-6-[8-chloro-4-hydroxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-2-oxo-chromen-7-yl]oxy-5-hydroxy-3-methoxy-2,2-dimethyl-tetrahydropyran-4-yl] 5-methyl-1H-pyrrole-2-carboxylate

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 3

Molecular Weight (mw)

697.1

Logarithm of the Partition Coefficient (xlogp)

5.3

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C35H37ClN2O11
IUPAC Name: [(3R,4S,5R,6S)-6-[8-chloro-4-hydroxy-3-[[4-hydroxy-3-(3-methylbut-2-enyl)benzoyl]amino]-2-oxochromen-7-yl]oxy-5-hydroxy-3-methoxy-2,2-dimethyloxan-4-yl] 5-methyl-1H-pyrrole-2-carboxylate
Canonical 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(=C(C(=O)O4)NC(=O)C5=CC(=C(C=C5)O)CC=C(C)C)O)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/h7-8,10-15,27,29-30,34,37,39-41H,9H2,1-6H3,(H,38,42)/t27-,29+,30-,34-/m1/s1
InChIKey: FJAQNRBDVKIIKK-LFLQOBSNSA-N

Cross-matching ID

PubChem CID: 54706138
CAS Number: 39868-96-7
DrugBank ID: DB03966
TTD ID: D0C9BH

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
DNA topoisomerase II (TOP2)	TT0IHXV	TOP2A_HUMAN ; TOP2B_HUMAN	Inhibitor	[1]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	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.