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CHEBI:65719 - cytosporic acid

Default Structure
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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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.
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