(+)-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

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Formula

C15H22O2

Net Charge

Average Mass

234.33400

Monoisotopic Mass

234.16198

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.

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

Last Modified

07 September 2017