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CHEBI:65408 - andrographolide

Default Structure
ChEBI IDCHEBI:65408
ChEBI Nameandrographolide
Stars
DefinitionA labdane diterpenoid isolated from the leaves and roots of Andrographis paniculata that exhibits anti-HIV, anti-inflammatory and antineoplastic properties.
Last Modified16 November 2012
DownloadsMolfile
FormulaC20H30O5
Net Charge0
Average Mass350.455
Monoisotopic Mass350.20932
SMILES[H][C@]12CCC(=C)[C@@H](C/C=C3/C(=O)OC[C@H]3O)[C@]1(C)CC[C@@H](O)[C@@]2(C)CO
InChIInChI=1S/C20H30O5/c1-12-4-7-16-19(2,9-8-17(23)20(16,3)11-21)14(12)6-5-13-15(22)10-25-18(13)24/h5,14-17,21-23H,1,4,6-11H2,2-3H3/b13-5+/t14-,15-,16+,17-,19+,20+/m1/s1
InChIKeyBOJKULTULYSRAS-OTESTREVSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Andrographis paniculata (ncbitaxon:175694)
leaf (BTO:0000713) PubMed (15894448)
root (BTO:0001188) PubMed (15894448)
leaf (BTO:0000713) PubMed (22026410) Dried leaves
Roles Classification
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.
Applications:
anti-inflammatory drug  A substance that reduces or suppresses inflammation.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
andrographolide (CHEBI:65408) has role anti-HIV agent (CHEBI:64946)
andrographolide (CHEBI:65408) has role anti-inflammatory drug (CHEBI:35472)
andrographolide (CHEBI:65408) has role antineoplastic agent (CHEBI:35610)
andrographolide (CHEBI:65408) has role metabolite (CHEBI:25212)
andrographolide (CHEBI:65408) is a carbobicyclic compound (CHEBI:36785)
andrographolide (CHEBI:65408) is a labdane diterpenoid (CHEBI:36770)
andrographolide (CHEBI:65408) is a primary alcohol (CHEBI:15734)
andrographolide (CHEBI:65408) is a secondary alcohol (CHEBI:35681)
andrographolide (CHEBI:65408) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(3E,4S)-4-hydroxy-3-{2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylidenedecahydronaphthalen-1-yl]ethylidene}dihydrofuran-2(3H)-one
Synonyms  Source
(1R-(1-α(E(S)),4aβ,5α,6α,8aα))-3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylene-1-naphthalenyl)ethylidene)dihydro-4-hydroxy-2(3H)-furanoneChemIDplus
3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenenaphthyl)ethylidene)dihydro-4-hydroxyfuran-2(3H)-oneChemIDplus
3α,14,15,18-tetrahydroxy-5b,9bH,10a-labda-8(20),12-dien-16-oic acid γ-LactoneChEBI
Manual XrefsDatabases
AndrographolideWikipedia
C20214KEGG COMPOUND
CN102397273Patent
EP2411004Patent
Registry NumbersSources
Reaxys:5609598Reaxys
CAS:5508-58-7ChemIDplus
Citations