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CHEBI:66153 - salaspermic acid

ChEBI IDCHEBI:66153
ChEBI Namesalaspermic acid
Stars
DefinitionA hexacyclic triterpenoid that is D:A-friedooleanan-29-oic acid substituted by a hydroxy group at position 3 and an epoxy group across positions 3 and 24 (the (3β,20α stereoisomer). Isolated from Salacia macrosperma and Tripterygium wilfordii, it exhibits anti-HIV activity.
Last Modified23 November 2016
DownloadsMolfile
FormulaC30H48O4
Net Charge0
Average Mass472.710
Monoisotopic Mass472.35526
SMILES[H][C@]12CC[C@@]34CO[C@@](O)(CC[C@@]3([H])[C@]1(C)CC[C@@]1(C)[C@]3([H])C[C@](C)(C(=O)O)CC[C@]3(C)CC[C@]21C)[C@@H]4C
InChIInChI=1S/C30H48O4/c1-19-29-9-7-20-26(4,21(29)8-10-30(19,33)34-18-29)14-16-28(6)22-17-25(3,23(31)32)12-11-24(22,2)13-15-27(20,28)5/h19-22,33H,7-18H2,1-6H3,(H,31,32)/t19-,20+,21+,22-,24-,25-,26-,27-,28+,29+,30+/m1/s1
InChIKeyZXENWDWQTWYUGY-UUZWCOCASA-N
Species of MetaboliteComponentSourceComments
Salacia macrosperma (IPNI:162634-1) - DOI (10.1039/P19790000349)
Tripterygium wilfordii (ncbitaxon:458696) root (BTO:0001188) PubMed (1375626)
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 reverse transcriptase inhibitor  An entity which inhibits the activity of HIV-1 reverse transcriptase.
ChEBI Ontology
Outgoing Relation(s)
salaspermic acid (CHEBI:66153) has parent hydride friedelane (CHEBI:71575)
salaspermic acid (CHEBI:66153) has role HIV-1 reverse transcriptase inhibitor (CHEBI:53756)
salaspermic acid (CHEBI:66153) has role metabolite (CHEBI:25212)
salaspermic acid (CHEBI:66153) is a cyclic hemiketal (CHEBI:59780)
salaspermic acid (CHEBI:66153) is a hexacyclic triterpenoid (CHEBI:70994)
salaspermic acid (CHEBI:66153) is a hydroxy monocarboxylic acid (CHEBI:35868)
IUPAC Name 
(3S,5aR,7aS,7bR,9aS,12R,13aR,13bS,15aR,15bS,16R)-3-hydroxy-7b,9a,12,13b,15a,16-hexamethylicosahydro-3,5a-methanochryseno[2,1-c]oxepine-12(5H)-carboxylic acid
Synonym  Source
(3β,20α)-3,24-epoxy-3-hydroxy-D:A-friedooleanan-29-oic acidChemIDplus
Registry NumbersSources
Reaxys:4889115Reaxys
CAS:71247-78-4ChemIDplus
Citations