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CHEBI:65408 - andrographolide

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:
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.
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