CHEBI:66153 - salaspermic acid

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ChEBI Name salaspermic acid
ChEBI ID CHEBI:66153
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C30H48O4
Net Charge 0
Average Mass 472.69970
Monoisotopic Mass 472.35526
InChI InChI=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
InChIKey ZXENWDWQTWYUGY-UUZWCOCASA-N
SMILES [H][C@@]12CC[C@]3(O)OC[C@@]1(CC[C@@]1([H])[C@@]2(C)CC[C@@]2(C)[C@]4([H])C[C@@](C)(CC[C@]4(C)CC[C@]12C)C(O)=O)[C@H]3C
Metabolite of Species Details
Salacia macrosperma (IPNI:162634-1) See: DOI
Tripterygium wilfordii (NCBI:txid458696) Found in root (BTO:0001188). See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 acid ChemIDplus
Registry Numbers Types Sources
4889115 Reaxys Registry Number Reaxys
71247-78-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
1375626 PubMed citation Europe PMC
17972583 PubMed citation Europe PMC
338605 Chinese Abstracts citation Europe PMC
371262 Chinese Abstracts citation Europe PMC
379028 Chinese Abstracts citation Europe PMC
7720147 PubMed citation Europe PMC
8158155 PubMed citation Europe PMC
Last Modified
23 November 2016