CHEBI:65778 - 16β,17-dihydroxy-ent-kaurane-19-oic acid

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ChEBI Name 16β,17-dihydroxy-ent-kaurane-19-oic acid
ChEBI ID CHEBI:65778
ChEBI ASCII Name 16beta,17-dihydroxy-ent-kaurane-19-oic acid
Definition A ent-kaurane diterpenoid that is ent-kaurane-19-oic acid substituted by hydroxy groups at positions 16 and 17 (the 16β stereoisomer). It is isolated from Helianthus sp. and Annona squamosa and exhibits anti-HIV activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H32O4
Net Charge 0
Average Mass 336.46570
Monoisotopic Mass 336.23006
InChI InChI=1S/C20H32O4/c1-17-7-3-8-18(2,16(22)23)14(17)6-9-19-10-13(4-5-15(17)19)20(24,11-19)12-21/h13-15,21,24H,3-12H2,1-2H3,(H,22,23)/t13-,14+,15+,17-,18-,19+,20-/m1/s1
InChIKey MRBLTWPEPGRXQN-WMUQSPHGSA-N
SMILES C[C@@]12CCC[C@](C)([C@H]1CC[C@@]13C[C@@H](CC[C@@H]21)[C@](O)(CO)C3)C(O)=O
Metabolite of Species Details
Annona squamosa (NCBI:txid301693) Found in fruit (BTO:0000486). Fresh fruit See: PubMed
Annona reticulata (NCBI:txid301862) Found in stem (BTO:0001300). Previous component: stem bark; See: DOI
Helianthus (NCBI:txid4231) See: DOI
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): anti-HIV agent
An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 16β,17-dihydroxy-ent-kaurane-19-oic acid (CHEBI:65778) has role anti-HIV agent (CHEBI:64946)
16β,17-dihydroxy-ent-kaurane-19-oic acid (CHEBI:65778) has role metabolite (CHEBI:25212)
16β,17-dihydroxy-ent-kaurane-19-oic acid (CHEBI:65778) is a ent-kaurane diterpenoid (CHEBI:36760)
16β,17-dihydroxy-ent-kaurane-19-oic acid (CHEBI:65778) is a bridged compound (CHEBI:35990)
16β,17-dihydroxy-ent-kaurane-19-oic acid (CHEBI:65778) is a diol (CHEBI:23824)
16β,17-dihydroxy-ent-kaurane-19-oic acid (CHEBI:65778) is a hydroxy monocarboxylic acid (CHEBI:35868)
16β,17-dihydroxy-ent-kaurane-19-oic acid (CHEBI:65778) is a primary alcohol (CHEBI:15734)
16β,17-dihydroxy-ent-kaurane-19-oic acid (CHEBI:65778) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(5β,8α,9β,10α)-16,17-dihydroxykauran-18-oic acid
Synonym Source
16β,17-dihydroxy-ent-kaurane-19-oic acid ChEBI
Registry Number Type Source
5382270 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
8786370 PubMed citation Europe PMC
Last Modified
26 March 2014