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

ChEBI IDCHEBI:65778
ChEBI Name16β,17-dihydroxy-ent-kaurane-19-oic acid
Stars
ASCII Name16beta,17-dihydroxy-ent-kaurane-19-oic acid
DefinitionA 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.
Last Modified26 March 2014
DownloadsMolfile
FormulaC20H32O4
Net Charge0
Average Mass336.472
Monoisotopic Mass336.23006
SMILES[H][C@@]12CC[C@]3([H])[C@@](CC[C@@]4([H])[C@@]3(C)CCC[C@@]4(C)C(=O)O)(C1)C[C@@]2(O)CO
InChIInChI=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
InChIKeyMRBLTWPEPGRXQN-WMUQSPHGSA-N
Species of MetaboliteComponentSourceComments
Helianthus (ncbitaxon:4231) - DOI (10.1016/S0031-9422(00)80485-9)
Annona squamosa (ncbitaxon:301693) fruit (BTO:0000486) PubMed (8786370) Fresh fruit
Annona reticulata (ncbitaxon:301862) stem (BTO:0001300) DOI (10.1021/np50053a043) Previous component: stem bark;
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
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.
ChEBI Ontology
Outgoing Relation(s)
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 acidChEBI
Registry NumbersSources
Reaxys:5382270Reaxys
Citations