CHEBI:137354 - (4Z,7Z,10Z,12E,14S,16Z,19Z,21R)-dihydroxydocosahexaenoic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name (4Z,7Z,10Z,12E,14S,16Z,19Z,21R)-dihydroxydocosahexaenoic acid
ChEBI ID CHEBI:137354
ChEBI ASCII Name (4Z,7Z,10Z,12E,14S,16Z,19Z,21R)-dihydroxydocosahexaenoic acid
Definition A dihydroxydocosahexaenoic acid that is (4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoic acid in which the two hydroxy substituents are located at the 14S- and 21R-positions.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Bijay
Secondary ChEBI IDs CHEBI:140213
Supplier Information
Download Molfile XML SDF
Formula C22H32O4
Net Charge 0
Average Mass 360.488
Monoisotopic Mass 360.23006
InChI InChI=1S/C22H32O4/c1-20(23)16-12-10-11-14-18-21(24)17-13-8-6-4-2-3-5-7-9-15-19-22(25)26/h2-3,6-9,11-14,16-17,20-21,23-24H,4-5,10,15,18-19H2,1H3,(H,25,26)/b3-2-,8-6-,9-7-,14-11-,16-12-,17-13+/t20-,21-/m1/s1
InChIKey FRJZMMUVPROLHN-KZPAZRNKSA-N
SMILES C(C(O)=O)C/C=C\C/C=C\C\C=C/C=C/[C@H](C/C=C\C/C=C\[C@@H](C)O)O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) See: PubMed
Homo Sapiens (NCBI:txid9606) Found in blood (UBERON:0000178). See: PubMed
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): human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
apoptosis inhibitor
Any substance that inhibits the process of apoptosis (programmed cell death) in multi-celled organisms.
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
Application(s): angiogenesis inhibitor
An agent and endogenous substances that antagonize or inhibit the development of new blood vessels.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (4Z,7Z,10Z,12E,14S,16Z,19Z,21R)-dihydroxydocosahexaenoic acid (CHEBI:137354) has role angiogenesis inhibitor (CHEBI:48422)
(4Z,7Z,10Z,12E,14S,16Z,19Z,21R)-dihydroxydocosahexaenoic acid (CHEBI:137354) has role apoptosis inhibitor (CHEBI:68494)
(4Z,7Z,10Z,12E,14S,16Z,19Z,21R)-dihydroxydocosahexaenoic acid (CHEBI:137354) has role human xenobiotic metabolite (CHEBI:76967)
(4Z,7Z,10Z,12E,14S,16Z,19Z,21R)-dihydroxydocosahexaenoic acid (CHEBI:137354) has role mouse metabolite (CHEBI:75771)
(4Z,7Z,10Z,12E,14S,16Z,19Z,21R)-dihydroxydocosahexaenoic acid (CHEBI:137354) is a dihydroxydocosahexaenoic acid (CHEBI:137348)
(4Z,7Z,10Z,12E,14S,16Z,19Z,21R)-dihydroxydocosahexaenoic acid (CHEBI:137354) is conjugate acid of (4Z,7Z,10Z,12E,14S,16Z,19Z,21R)-dihydroxydocosahexaenoate (CHEBI:136533)
(4Z,7Z,10Z,12E,14S,16Z,19Z,21R)-dihydroxydocosahexaenoic acid (CHEBI:137354) is enantiomer of (4Z,7Z,10Z,12E,14R,16Z,19Z,21S)-dihydroxydocosahexaenoic acid (CHEBI:137368)
Incoming (4Z,7Z,10Z,12E,14S,16Z,19Z,21R)-dihydroxydocosahexaenoate (CHEBI:136533) is conjugate base of (4Z,7Z,10Z,12E,14S,16Z,19Z,21R)-dihydroxydocosahexaenoic acid (CHEBI:137354)
(4Z,7Z,10Z,12E,14R,16Z,19Z,21S)-dihydroxydocosahexaenoic acid (CHEBI:137368) is enantiomer of (4Z,7Z,10Z,12E,14S,16Z,19Z,21R)-dihydroxydocosahexaenoic acid (CHEBI:137354)
IUPAC Name
(4Z,7Z,10Z,12E,14S,16Z,19Z,21R)-14,21-dihydroxydocosa-4,7,10,12,16,19-hexaenoic acid
Synonyms Sources
(14S,21R)-DiHDoHE ChEBI
(14S,21R)-dihydroxy-(4Z,7Z,10Z,12E,16Z,19Z)-docosahexaenoic acid ChEBI
14(S),21(R)-diHDHA SUBMITTER
14(S),21(R)-dihydroxydocosahexaenoic acid ChEBI
14S,21R-diHDHA ChEBI
Citations Waiting for Citations Types Sources
19965612 PubMed citation Europe PMC
21112969 PubMed citation Europe PMC
21839062 PubMed citation Europe PMC
21846180 PubMed citation Europe PMC
23386851 PubMed citation Europe PMC
Last Modified
22 February 2018