CHEBI:28368 - novobiocin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name novobiocin
ChEBI ID CHEBI:28368
Definition A coumarin-derived antibiotic obtained from Streptomyces niveus.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44505, CHEBI:7644, CHEBI:25597
Supplier Information
Download Molfile XML SDF
more structures >>
Formula C31H36N2O11
Net Charge 0
Average Mass 612.62430
Monoisotopic Mass 612.232
InChI InChI=1S/C31H36N2O11/c1-14(2)7-8-16-13-17(9-11-19(16)34)27(37)33-21-22(35)18-10-12-20(15(3)24(18)42-28(21)38)41-29-23(36)25(43-30(32)39)26(40-6)31(4,5)44-29/h7,9-13,23,25-26,29,34-36H,8H2,1-6H3,(H2,32,39)(H,33,37)/t23-,25+,26-,29-/m1/s1
InChIKey YJQPYGGHQPGBLI-KGSXXDOSSA-N
SMILES CO[C@@H]1[C@@H](OC(N)=O)[C@@H](O)[C@H](Oc2ccc3c(O)c(NC(=O)c4ccc(O)c(CC=C(C)C)c4)c(=O)oc3c2C)OC1(C)C
Metabolite of Species Details
Streptomyces niveus (NCBI:193462) See: PubMed
Escherichia coli (NCBI:562) See: PubMed
Roles Classification
Biological Role(s): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antibacterial agent
A substance that kills or slows the growth of bacteria.
Application(s): hepatoprotective agent
Any compound that is able to prevent damage to the liver.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing novobiocin (CHEBI:28368) has role Escherichia coli metabolite (CHEBI:76971)
novobiocin (CHEBI:28368) has role antibacterial agent (CHEBI:33282)
novobiocin (CHEBI:28368) has role antimicrobial agent (CHEBI:33281)
novobiocin (CHEBI:28368) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
novobiocin (CHEBI:28368) has role hepatoprotective agent (CHEBI:62868)
novobiocin (CHEBI:28368) is a carbamate ester (CHEBI:23003)
novobiocin (CHEBI:28368) is a ether (CHEBI:25698)
novobiocin (CHEBI:28368) is a hexoside (CHEBI:35313)
novobiocin (CHEBI:28368) is a hydroxycoumarin (CHEBI:37912)
novobiocin (CHEBI:28368) is a monocarboxylic acid amide (CHEBI:29347)
novobiocin (CHEBI:28368) is a monosaccharide derivative (CHEBI:63367)
novobiocin (CHEBI:28368) is a phenols (CHEBI:33853)
novobiocin (CHEBI:28368) is conjugate acid of novobiocin(1−) (CHEBI:71339)
Incoming novobiocin(1−) (CHEBI:71339) is conjugate base of novobiocin (CHEBI:28368)
INNs Sources
novobiocina DrugBank
novobiocine DrugBank
novobiocinum DrugBank
Synonyms Sources
N-{7-[(3-O-carbamoyl-6-deoxy-5-methyl-4-O-methyl-β-D-gulopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo-2H-chromen-3-yl}-4-hydroxy-3-(3-methylbut-2-en-1-yl)benzamide ChEBI
Novobiocin KEGG COMPOUND
Database Links Databases
1974 DrugCentral
C00002487 KNApSAcK
C05080 KEGG COMPOUND
DB01051 DrugBank
HMDB0015185 HMDB
LSM-5910 LINCS
NOV PDBeChem
WO2012049521 Patent
WO2012103487 Patent
View more database links
Registry Numbers Types Sources
1445842 Reaxys Registry Number Reaxys
303-81-1 CAS Registry Number KEGG COMPOUND
303-81-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
17132020 PubMed citation Europe PMC
18418407 PubMed citation Europe PMC
19282394 PubMed citation Europe PMC
19762445 PubMed citation Europe PMC
20325309 PubMed citation Europe PMC
21388139 PubMed citation Europe PMC
22897434 PubMed citation Europe PMC
26844397 PubMed citation Europe PMC
26926630 PubMed citation Europe PMC
27829510 PubMed citation Europe PMC
27914946 PubMed citation Europe PMC
28246042 PubMed citation Europe PMC
28316592 PubMed citation Europe PMC
9687383 PubMed citation Europe PMC
Last Modified
27 March 2017