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CHEBI:65487 - platanic acid

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
Syzygium claviflorum (ncbitaxon:219860) leaf (BTO:0000713) PubMed (8176401)
Breynia fruticosa (ncbitaxon:296042) root (BTO:0001188) PubMed (21428418) 90% Methanolic extract of air-dried, crushed roots.
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)
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