isovanillobiocin   Click here for help

GtoPdb Ligand ID: 12129

Synonyms: novclobiocin 312
Comment: Isovanillobiocin is an aminocoumarin antibacterial compound isolated from the culture broth of a cloQ- mutant of the clorobiocin producer Streptomyces roseochromogenes [1]. The same study also identified vanillobiocin and declovanillobiocin.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 5
Rotatable bonds 10
Topological polar surface area 199.01
Molecular weight 658.16
XLogP 4.51
No. Lipinski's rules broken 0
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Canonical SMILES CO[C@@H]1[C@@H](O)[C@@H](OC(=O)c2ccc([nH]2)C)[C@@H](OC1(C)C)Oc1ccc2c(c1Cl)oc(=O)c(c2O)NC(=O)c1ccc(c(c1)OC)O
Isomeric SMILES Cc1ccc([nH]1)C(=O)O[C@@H]1[C@@H]([C@H](C(O[C@H]1Oc1c(c2c(cc1)c(c(c(=O)o2)NC(=O)c1cc(c(cc1)O)OC)O)Cl)(C)C)OC)O
InChI InChI=1S/C31H31ClN2O12/c1-13-6-9-16(33-13)28(39)45-25-23(37)26(42-5)31(2,3)46-30(25)43-18-11-8-15-22(36)21(29(40)44-24(15)20(18)32)34-27(38)14-7-10-17(35)19(12-14)41-4/h6-12,23,25-26,30,33,35-37H,1-5H3,(H,34,38)/t23-,25+,26+,30+/m0/s1
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
[(2S,3R,4R,5R)-2-[8-chloro-4-hydroxy-3-[(4-hydroxy-3-methoxybenzoyl)amino]-2-oxochromen-7-yl]oxy-4-hydroxy-5-methoxy-6,6-dimethyloxan-3-yl] 5-methyl-1H-pyrrole-2-carboxylate
Synonyms Click here for help
novclobiocin 312
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Isovanillobiocin
Other databases
CAS Registry No. 744218-19-7 (source: Scifinder)
ChEMBL Ligand CHEMBL1275899
GtoPdb PubChem SID 472319251
PubChem CID 54713406
Search Google for chemical match using the InChIKey AKYRQFMQZJFLAE-AUHTVUCRSA-N
Search Google for chemicals with the same backbone AKYRQFMQZJFLAE
UniChem Compound Search for chemical match using the InChIKey AKYRQFMQZJFLAE-AUHTVUCRSA-N
UniChem Connectivity Search for chemical match using the InChIKey AKYRQFMQZJFLAE-AUHTVUCRSA-N