CHEBI:17710 - (R)-mevalonic acid

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ChEBI Name (R)-mevalonic acid
ChEBI ID CHEBI:17710
ChEBI ASCII Name (R)-mevalonic acid
Definition The (R)-enantiomer of mevalonic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:345, CHEBI:18691
Supplier Information ChemicalBook:CB9666441, ChemicalBook:CB2112323, eMolecules:524832, ZINC000003802189
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α-Linolenic acid, also known as alpha-linolenic acid (ALA) (from Greek alpha meaning "first" and linon meaning flax), is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils. In terms of its structure, it is named all-cis-9,12,15-octadecatrienoic acid. In physiological literature, it is listed by its lipid number, 18:3 (n−3). It is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the methyl end of the fatty acid chain, known as the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is a regioisomer of gamma-linolenic acid (GLA), an 18:3 (n−6) fatty acid (i.e., a polyunsaturated omega-6 fatty acid with three double bonds).
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Formula C6H12O4
Net Charge 0
Average Mass 148.15710
Monoisotopic Mass 148.07356
InChI InChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)/t6-/m1/s1
InChIKey KJTLQQUUPVSXIM-ZCFIWIBFSA-N
SMILES C[C@@](O)(CCO)CC(O)=O
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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ChEBI Ontology
Outgoing (R)-mevalonic acid (CHEBI:17710) is a 3,5-dihydroxy-3-methylpentanoic acid (CHEBI:194519)
(R)-mevalonic acid (CHEBI:17710) is conjugate acid of (R)-mevalonate (CHEBI:36464)
(R)-mevalonic acid (CHEBI:17710) is enantiomer of (S)-mevalonic acid (CHEBI:28880)
Incoming (R)-3-phosphomevalonic acid (CHEBI:83564) has functional parent (R)-mevalonic acid (CHEBI:17710)
(R)-5-diphosphomevalonic acid (CHEBI:15899) has functional parent (R)-mevalonic acid (CHEBI:17710)
(R)-5-phosphomevalonic acid (CHEBI:17436) has functional parent (R)-mevalonic acid (CHEBI:17710)
mevalonic acid (CHEBI:25351) has part (R)-mevalonic acid (CHEBI:17710)
(R)-mevalonate (CHEBI:36464) is conjugate base of (R)-mevalonic acid (CHEBI:17710)
(S)-mevalonic acid (CHEBI:28880) is enantiomer of (R)-mevalonic acid (CHEBI:17710)
IUPAC Name
(3R)-3,5-dihydroxy-3-methylpentanoic acid
Synonyms Sources
(−)-mevalonic acid ChEBI
(3R)-3,5-dihydroxy-3-methylvaleric acid ChEBI
(3R)-mevalonic acid ChEBI
(R)-(−)-mevalonic acid ChEBI
(R)-3,5-dihydroxy-3-methylpentanoic acid ChEBI
(R)-3,5-dihydroxy-3-methylvaleric acid ChEBI
D-mevalonic acid ChEBI
R-mevalonic acid ChEBI
R-MVA ChEBI
Manual Xrefs Databases
C00001195 KNApSAcK
C00418 KEGG COMPOUND
DB03518 DrugBank
LMFA01050352 LIPID MAPS
Mevalonic_acid Wikipedia
View more database links
Registry Numbers Types Sources
1722593 Reaxys Registry Number Reaxys
17817-88-8 CAS Registry Number KEGG COMPOUND
Last Modified
23 March 2023