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CHEBI:66234 - TMC-1A

ChEBI IDCHEBI:66234
ChEBI NameTMC-1A
Stars
DefinitionA polyene antibiotic that is 2-amino-4,5-dihydroxycyclohex-2-en-1-one in which the hydrogen at position 4 is replaced by a by an all-E-6-carboxyhexa-1,3,5-trien-1-yl group; in which the amino group has been acylated by a (2E)-2,4-dimethyloct-2-enoyl group; and in which the carboxy group of the resulting carboxylic acid has been condensed with the amino group of 2-amino-3-hydroxycyclopent-2-en-1-one to give the corresponding carboxamide. TMC-1A is an antitumour antibiotic isolated from Streptomyces sp. A-230.
Last Modified7 March 2018
DownloadsMolfile
FormulaC28H36N2O7
Net Charge0
Average Mass512.603
Monoisotopic Mass512.25225
SMILESCCCCC(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](O)CC1=O
InChIInChI=1S/C28H36N2O7/c1-4-5-10-18(2)15-19(3)27(36)29-20-17-28(37,24(34)16-23(20)33)14-9-7-6-8-11-25(35)30-26-21(31)12-13-22(26)32/h6-9,11,14-15,17-18,24,31,34,37H,4-5,10,12-13,16H2,1-3H3,(H,29,36)(H,30,35)/b7-6+,11-8+,14-9+,19-15+/t18?,24-,28+/m1/s1
InChIKeyCCZRQXWCDVXNHR-GFLRHUPZSA-N
Species of MetaboliteComponentSourceComments
Streptomyces sp. (ncbitaxon:1931) - PubMed (9031666) Strain: A 230
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.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
TMC-1A (CHEBI:66234) has role antineoplastic agent (CHEBI:35610)
TMC-1A (CHEBI:66234) has role bacterial metabolite (CHEBI:76969)
TMC-1A (CHEBI:66234) is a cyclic ketone (CHEBI:3992)
TMC-1A (CHEBI:66234) is a enamide (CHEBI:51751)
TMC-1A (CHEBI:66234) is a enol (CHEBI:33823)
TMC-1A (CHEBI:66234) is a enone (CHEBI:51689)
TMC-1A (CHEBI:66234) is a polyene antibiotic (CHEBI:26177)
TMC-1A (CHEBI:66234) is a secondary alcohol (CHEBI:35681)
TMC-1A (CHEBI:66234) is a secondary carboxamide (CHEBI:140325)
TMC-1A (CHEBI:66234) is a tertiary alcohol (CHEBI:26878)
IUPAC Name 
(2E)-N-[(3S,4R)-3,4-dihydroxy-3-{(1E,3E,5E)-7-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)amino]-7-oxohepta-1,3,5-trien-1-yl}-6-oxocyclohex-1-en-1-yl]-2,4-dimethyloct-2-enamide
Registry NumbersSources
Reaxys:8178750Reaxys
Citations