CHEBI:29623 - manumycin A

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ChEBI Name manumycin A
ChEBI ID CHEBI:29623
Definition A polyketide with formula C31H38N2O7 initially isolated from Streptomyces parvulus as a result of a random screening program for farnesyl transferase (FTase) inhibitors. It is a natural product that exhibits anticancer and antibiotic properties.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C31H38N2O7
Net Charge 0
Average Mass 550.652
Monoisotopic Mass 550.26790
InChI InChI=1S/C31H38N2O7/c1-5-6-11-19(2)16-20(3)17-21(4)30(38)32-22-18-31(39,29-28(40-29)27(22)37)15-10-8-7-9-12-25(36)33-26-23(34)13-14-24(26)35/h7-10,12,15-19,28-29,34,39H,5-6,11,13-14H2,1-4H3,(H,32,38)(H,33,36)/b8-7+,12-9+,15-10+,20-16+,21-17+/t19-,28-,29-,31+/m1/s1
InChIKey TWWQHCKLTXDWBD-MVTGTTCWSA-N
SMILES CCCC[C@@H](C)\C=C(/C)\C=C(/C)C(=O)NC1=C[C@@](O)(\C=C\C=C\C=C\C(=O)NC2=C(O)CCC2=O)[C@@H]2O[C@@H]2C1=O
Metabolite of Species Details
Streptomyces parvulus (NCBI:txid146923) of strain Tu64 See: PubMed
Streptomyces sp. (NCBI:txid1931) of strain M045 See: PubMed
Roles Classification
Biological Role(s): EC 1.8.1.9 (thioredoxin reductase) inhibitor
An EC 1.8.1.* (oxidoreductase acting on sulfur group of donors, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of thioredoxin reductase (EC 1.8.1.9).
EC 2.5.1.58 (protein farnesyltransferase) inhibitor
An EC 2.5.1.* (non-methyl-alkyl or aryl transferase) inhibitor that interferes with the action of protein farnesyltransferase (EC 2.5.1.58), one of the three enzymes in the prenyltransferase group.
apoptosis inducer
Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
marine metabolite
Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
antiatherosclerotic agent
A cardiovascular drug that prevents atherosclerosis (a disease in which the inside of an artery narrows due to the build up of plaque). Compare with antiatherogenic agent.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing manumycin A (CHEBI:29623) has role antiatherosclerotic agent (CHEBI:145947)
manumycin A (CHEBI:29623) has role antimicrobial agent (CHEBI:33281)
manumycin A (CHEBI:29623) has role antineoplastic agent (CHEBI:35610)
manumycin A (CHEBI:29623) has role apoptosis inducer (CHEBI:68495)
manumycin A (CHEBI:29623) has role bacterial metabolite (CHEBI:76969)
manumycin A (CHEBI:29623) has role EC 1.8.1.9 (thioredoxin reductase) inhibitor (CHEBI:64670)
manumycin A (CHEBI:29623) has role EC 2.5.1.58 (protein farnesyltransferase) inhibitor (CHEBI:64133)
manumycin A (CHEBI:29623) has role marine metabolite (CHEBI:76507)
manumycin A (CHEBI:29623) is a enamide (CHEBI:51751)
manumycin A (CHEBI:29623) is a epoxide (CHEBI:32955)
manumycin A (CHEBI:29623) is a organic heterobicyclic compound (CHEBI:27171)
manumycin A (CHEBI:29623) is a polyketide (CHEBI:26188)
manumycin A (CHEBI:29623) is a secondary carboxamide (CHEBI:140325)
manumycin A (CHEBI:29623) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(2E,4E,6R)-N-[(1S,5S,6R)-5-hydroxy-5-{(1E,3E,5E)-7-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)amino]-7-oxohepta-1,3,5-trien-1-yl}-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyldeca-2,4-dienamide
Synonyms Sources
(−)-manumycin A ChEBI
(2E,4E,6R)-N-[(1S,5S,6R)-5-Hydroxy-5-[(1E,3E,5E)-7-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-7-oxo-1,3,5-heptatrien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2,4,6-trimethyl-2,4-decadienamide ChEBI
manumycin KEGG COMPOUND
manumycin A KEGG COMPOUND
NSC 622141 ChEBI
UCF 1C ChEBI
UCF1-C ChEBI
Manual Xrefs Databases
4942813 ChemSpider
C12111 KEGG COMPOUND
CPD-18768 MetaCyc
HMDB0242678 HMDB
LMFA08020185 LIPID MAPS
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Registry Number Type Source
52665-74-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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PMC3513075 PubMed Central citation Europe PMC
Last Modified
13 October 2021