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(+)-artemisinic acid (CHEBI:63749)

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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
See structure as:  Image  Applet
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Formula Source
C15H22O2 ChEBI
Net Charge 0
Average Mass 234.33400
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.
View more on the ChEBI Ontology
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 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 CiteXplore
17252486 PubMed citation CiteXplore
19194910 PubMed citation CiteXplore
20050663 PubMed citation CiteXplore
22396222 PubMed citation CiteXplore
2607353 PubMed citation CiteXplore
8053018 PubMed citation CiteXplore
9409011 PubMed citation CiteXplore
Last Modified
14 June 2012

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