manumycin A (CHEBI:29623)

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CHEBI:29623 - manumycin A

ChEBI ID	CHEBI:29623
ChEBI Name	manumycin A
Stars
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.
Last Modified	13 October 2021
Downloads	Molfile

Formula	C31H38N2O7
Net Charge	0
Average Mass	550.652
Monoisotopic Mass	550.26790
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
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

Species of Metabolite	Component	Source	Comments
Streptomyces parvulus (ncbitaxon:146923)	-	PubMed (8460134)	Strain: Tu64
Streptomyces sp. (ncbitaxon:1931)	-	PubMed (15787434)	Strain: M045

Roles Classification

Biological Roles:

bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria.

antimicrobial agent A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.

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.

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
(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	ChEBI
manumycin A	KEGG COMPOUND
NSC 622141	ChEBI
UCF1-C	ChEBI

Manual Xrefs	Databases
4942813	ChemSpider
C12111	KEGG COMPOUND
CPD-18768	MetaCyc
HMDB0242678	HMDB
LMFA08020185	LIPID MAPS

Registry Numbers	Sources
CAS:52665-74-4	ChemIDplus

Citations