CHEBI:34784 - hepoxilin B3

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name hepoxilin B3
ChEBI ID CHEBI:34784
ChEBI ASCII Name hepoxilin B3
Definition A hepoxilin having (5Z,9E,14Z) double bond stereochemistry, a 10-hydroxy substituent and an (11S,12S)-epoxy group.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information No supplier information found for this compound.
Download Molfile XML SDF
Formula C20H32O4
Net Charge 0
Average Mass 336.466
Monoisotopic Mass 336.23006
InChI InChI=1S/C20H32O4/c1-2-3-4-5-9-12-15-18-20(24-18)17(21)14-11-8-6-7-10-13-16-19(22)23/h6-7,9,11-12,14,17-18,20-21H,2-5,8,10,13,15-16H2,1H3,(H,22,23)/b7-6-,12-9-,14-11-/t17?,18-,20-/m0/s1
InChIKey DWNBPRRXEVJMPO-RNGYDEEPSA-N
SMILES C(\C([C@H]1[C@H](C/C=C\CCCCC)O1)O)=C\C/C=C\CCCC(=O)O
Metabolite of Species Details
Mus musculus (NCBI:txid10090) Found in bronchoalveolar lavage (BTO:0000155). See: MetaboLights Study
Mus musculus (NCBI:txid10090) See: MetaboLights Study
Mus musculus (NCBI:txid10090) See: MetaboLights Study
Mus musculus (NCBI:txid10090) Found in bronchoalveolar lavage (BTO:0000155). See: MetaboLights Study
Homo sapiens (NCBI:txid9606) See: PubMed
Cottoniella filamentosa (WORMS:144741) See: PubMed
Platysiphonia miniata (WORMS:144776) 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.
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing hepoxilin B3 (CHEBI:34784) has functional parent all-cis-icosa-5,8,14-trienoic acid (CHEBI:36202)
hepoxilin B3 (CHEBI:34784) has role algal metabolite (CHEBI:84735)
hepoxilin B3 (CHEBI:34784) has role human xenobiotic metabolite (CHEBI:76967)
hepoxilin B3 (CHEBI:34784) is a epoxy fatty acid (CHEBI:61498)
hepoxilin B3 (CHEBI:34784) is a hepoxilin (CHEBI:36200)
hepoxilin B3 (CHEBI:34784) is a hydroxy polyunsaturated fatty acid (CHEBI:140345)
hepoxilin B3 (CHEBI:34784) is a long-chain fatty acid (CHEBI:15904)
hepoxilin B3 (CHEBI:34784) is a trienoic fatty acid (CHEBI:73155)
hepoxilin B3 (CHEBI:34784) is conjugate acid of hepoxilin B3(1−) (CHEBI:78084)
Incoming hepoxilin B3(1−) (CHEBI:78084) is conjugate base of hepoxilin B3 (CHEBI:34784)
IUPAC Name
(5Z,8Z)-10-hydroxy-10-{(2S,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoic acid
Synonyms Sources
10-hydroxy-11S,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid LIPID MAPS
Hepoxilin B3 KEGG COMPOUND
HxB3 ChEBI
HXB3 ChEBI
Manual Xrefs Databases
C14810 KEGG COMPOUND
LMFA03090003 LIPID MAPS
View more database links
Registry Number Type Source
71799-95-6 CAS Registry Number ChemIDplus
Citations Types Sources
10692117 PubMed citation Europe PMC
11851887 PubMed citation Europe PMC
2180942 PubMed citation Europe PMC
Last Modified
21 August 2023
General Comment
2011-03-21 A normal human epidermis eicosanoid whose levels are dramatically elevated in psoriatic lesions.