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CHEBI:29623 - manumycin A

ChEBI IDCHEBI:29623
ChEBI Namemanumycin A
Stars
DefinitionA 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.
Last Modified13 October 2021
DownloadsMolfile
FormulaC31H38N2O7
Net Charge0
Average Mass550.652
Monoisotopic Mass550.26790
SMILESCCCC[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
InChIInChI=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
InChIKeyTWWQHCKLTXDWBD-MVTGTTCWSA-N
Species of MetaboliteComponentSourceComments
Streptomyces sp. (ncbitaxon:1931) - PubMed (15787434) Strain: M045
Streptomyces parvulus (ncbitaxon:146923) - PubMed (8460134) Strain: Tu64
Roles Classification
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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).
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
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.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
Applications:
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.
ChEBI Ontology
Outgoing Relation(s)
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  Source
manumycin AKEGG COMPOUND
manumycinKEGG COMPOUND
(−)-manumycin AChEBI
UCF 1CChEBI
NSC 622141ChEBI
(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-decadienamideChEBI
Manual XrefsDatabases
C12111KEGG COMPOUND
HMDB0242678HMDB
CPD-18768MetaCyc
LMFA08020185LIPID MAPS
4942813ChemSpider
Registry NumbersSources
CAS:52665-74-4ChemIDplus
Citations