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CHEBI:65487 - platanic acid

Default Structure
ChEBI IDCHEBI:65487
ChEBI Nameplatanic acid
Stars
DefinitionA pentacyclic triterpenoid that is 30-norlupan-28-oic acid substituted by a 3β-hydroxy and an oxo group at position 20. It is isolated from the leaves of Syzygium claviflorum and exhibits anti-HIV activity.
Last Modified20 November 2012
DownloadsMolfile
FormulaC29H46O4
Net Charge0
Average Mass458.683
Monoisotopic Mass458.33961
SMILES[H][C@]12CC[C@@]3([H])[C@@](C)(CC[C@@]4(C(=O)O)CC[C@@H](C(C)=O)[C@@]43[H])[C@]1(C)CC[C@@]1([H])C(C)(C)[C@@H](O)CC[C@]21C
InChIInChI=1S/C29H46O4/c1-17(30)18-9-14-29(24(32)33)16-15-27(5)19(23(18)29)7-8-21-26(4)12-11-22(31)25(2,3)20(26)10-13-28(21,27)6/h18-23,31H,7-16H2,1-6H3,(H,32,33)/t18-,19+,20-,21+,22-,23+,26-,27+,28+,29-/m0/s1
InChIKeyRVMPLOSJMIQORE-FUAAEJBOSA-N
Species of MetaboliteComponentSourceComments
Breynia fruticosa (ncbitaxon:296042) root (BTO:0001188) PubMed (21428418) 90% Methanolic extract of air-dried, crushed roots.
Syzygium claviflorum (ncbitaxon:219860) leaf (BTO:0000713) PubMed (8176401)
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.
anti-HIV agent  An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
ChEBI Ontology
Outgoing Relation(s)
platanic acid (CHEBI:65487) has role anti-HIV agent (CHEBI:64946)
platanic acid (CHEBI:65487) has role metabolite (CHEBI:25212)
platanic acid (CHEBI:65487) is a hydroxy monocarboxylic acid (CHEBI:35868)
platanic acid (CHEBI:65487) is a methyl ketone (CHEBI:51867)
platanic acid (CHEBI:65487) is a pentacyclic triterpenoid (CHEBI:25872)
IUPAC Name 
(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bS)-1-acetyl-9-hydroxy-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid
Synonym  Source
3β-hydroxy-20-oxo-30-norlupan-28-oic acidChemIDplus
Registry NumbersSources
Reaxys:2681373Reaxys
CAS:6060-06-6ChemIDplus
Citations