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CHEBI:65719 - cytosporic acid

ChEBI IDCHEBI:65719
ChEBI Namecytosporic acid
Stars
DefinitionA monocarboxylic acid that is 3,8-dimethyl-5-oxo-1,2,3,4,4a,8a-hexahydronaphthalene-1-carboxylic acid substituted by a (2R)-hexan-2-yl at position 7, a hydroxy group at position 6 and a 3-hydroxypropanoyl group at position 8. It is a fungal metabolite produced by Cytospora with HIV-1 integrase inhibitory activity.
Last Modified23 September 2018
DownloadsMolfile
FormulaC22H34O6
Net Charge0
Average Mass394.508
Monoisotopic Mass394.23554
SMILES[H][C@@]12[C@@H](C(=O)O)C[C@@H](C)C[C@@]1([H])C(=O)C(O)=C([C@H](C)CCCC)[C@@]2(C)C(=O)CCO
InChIInChI=1S/C22H34O6/c1-5-6-7-13(3)17-20(26)19(25)14-10-12(2)11-15(21(27)28)18(14)22(17,4)16(24)8-9-23/h12-15,18,23,26H,5-11H2,1-4H3,(H,27,28)/t12-,13+,14+,15-,18-,22+/m0/s1
InChIKeyDHAUNSINPICAFU-DSGRLQPCSA-N
Species of MetaboliteComponentSourceComments
Cytospora (ncbitaxon:117544) - PubMed (12713414)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
HIV-1 integrase inhibitor  An inhibitor of HIV-1 integrase, an enzyme required for the integration of the genetic material of the retrovirus into the DNA of the infected cells.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
cytosporic acid (CHEBI:65719) has role HIV-1 integrase inhibitor (CHEBI:67268)
cytosporic acid (CHEBI:65719) has role metabolite (CHEBI:25212)
cytosporic acid (CHEBI:65719) is a cyclic ketone (CHEBI:3992)
cytosporic acid (CHEBI:65719) is a dioxo monocarboxylic acid (CHEBI:35951)
cytosporic acid (CHEBI:65719) is a enol (CHEBI:33823)
cytosporic acid (CHEBI:65719) is a hexahydronaphthalenes (CHEBI:142348)
cytosporic acid (CHEBI:65719) is a primary alcohol (CHEBI:15734)
cytosporic acid (CHEBI:65719) is a β-hydroxy ketone (CHEBI:55380)
IUPAC Name 
(1S,3S,4aR,8S,8aS)-7-[(2R)-hexan-2-yl]-6-hydroxy-8-(3-hydroxypropanoyl)-3,8-dimethyl-5-oxo-1,2,3,4,4a,8a-hexahydronaphthalene-1-carboxylic acid
Synonym  Source
(1S,3S,4aR,8S,8aS) 1,2,3,4,4a,5,8,8a-octahydro-6-hydroxy-8-(3-hydroxy-1-oxopropyl)-3,8-dimethyl-7-[(1R)-1-methylpentyl]-5-oxo-1-naphthalenecarboxylic acidChEBI
Registry NumbersSources
Reaxys:9533928Reaxys
Citations