CHEBI:63749 - (+)-artemisinic acid

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ChEBI Name (+)-artemisinic acid
ChEBI ID CHEBI:63749
Definition A monocarboxylic acid that is prop-2-enoic acid which is substituted at position 2 by a 4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl group (the 1S,4R,4aS,8aR diastereoisomer). It is a sesquiterpenoid precursor of artemisinin, obtained from sweet wormwood, Artemisia annua.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C15H22O2
Net Charge 0
Average Mass 234.33400
Monoisotopic Mass 234.162
InChI InChI=1S/C15H22O2/c1-9-4-6-12-10(2)5-7-13(14(12)8-9)11(3)15(16)17/h8,10,12-14H,3-7H2,1-2H3,(H,16,17)/t10-,12+,13+,14+/m1/s1
InChIKey PLQMEXSCSAIXGB-SAXRGWBVSA-N
SMILES [H][C@@]12CCC(C)=C[C@]1([H])[C@@H](CC[C@H]2C)C(=C)C(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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ChEBI Ontology
Outgoing (+)-artemisinic acid (CHEBI:63749) has functional parent (+)-artemisinic alcohol (CHEBI:64783)
(+)-artemisinic acid (CHEBI:63749) has role metabolite (CHEBI:25212)
(+)-artemisinic acid (CHEBI:63749) is a carbobicyclic compound (CHEBI:36785)
(+)-artemisinic acid (CHEBI:63749) is a monocarboxylic acid (CHEBI:25384)
(+)-artemisinic acid (CHEBI:63749) is a octahydronaphthalenes (CHEBI:138397)
(+)-artemisinic acid (CHEBI:63749) is a sesquiterpenoid (CHEBI:26658)
(+)-artemisinic acid (CHEBI:63749) is conjugate acid of (+)-artemisinate (CHEBI:64782)
Incoming (+)-artemisinate (CHEBI:64782) is conjugate base of (+)-artemisinic acid (CHEBI:63749)
IUPAC Name
2-[(1R,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]prop-2-enoic acid
Synonyms Sources
artemisic acid ChemIDplus
artemisinic acid ChemIDplus
Database Links Databases
CPD-13248 MetaCyc
WO2009085068 Patent
View more database links
Registry Numbers Types Sources
3546102 Reaxys Registry Number Reaxys
80286-58-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
16612385 PubMed citation Europe PMC
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20050663 PubMed citation Europe PMC
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Last Modified
07 September 2017