CHEBI:65408 - andrographolide

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ChEBI Name andrographolide
ChEBI ID CHEBI:65408
Definition A labdane diterpenoid isolated from the leaves and roots of Andrographis paniculata that exhibits anti-HIV, anti-inflammatory and antineoplastic properties.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C20H30O5
Net Charge 0
Average Mass 350.44920
InChI InChI=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
InChIKey BOJKULTULYSRAS-OTESTREVSA-N
SMILES [H][C@]12CCC(=C)[C@@H](C\C=C3/[C@H](O)COC3=O)[C@]1(C)CC[C@@H](O)[C@@]2(C)CO
Metabolite of Species Details
Andrographis paniculata (NCBI:175694) Found in leaf (BTO:0000713). Dried leaves See: PubMed
Andrographis paniculata (NCBI:175694) Found in leaf (BTO:0000713). See: PubMed
Andrographis paniculata (NCBI:175694) Found in root (BTO:0001188). See: PubMed
Roles Classification
Biological Role(s): 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.
Application(s): anti-inflammatory drug
A substance that reduces or suppresses inflammation.
anti-HIV agent
An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 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 γ-lactone (CHEBI:37581)
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)
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 Sources
(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)-furanone ChemIDplus
3-(2-(decahydro-6-hydroxy-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenenaphthyl)ethylidene)dihydro-4-hydroxyfuran-2(3H)-one ChemIDplus
3α,14,15,18-tetrahydroxy-5b,9bH,10a-labda-8(20),12-dien-16-oic acid γ-Lactone ChEBI
Database Links Databases
Andrographolide Wikipedia
C20214 KEGG COMPOUND
CN102397273 Patent
EP2411004 Patent
View more database links
Registry Numbers Types Sources
5508-58-7 CAS Registry Number ChemIDplus
5609598 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15894448 PubMed citation CiteXplore
18464090 PubMed citation CiteXplore
19110075 PubMed citation CiteXplore
22026410 PubMed citation CiteXplore
22512591 PubMed citation CiteXplore
22858223 PubMed citation CiteXplore
Last Modified
16 November 2012