CHEBI:80658 - 5,6-epoxyretinoic acid

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ChEBI Name 5,6-epoxyretinoic acid
ChEBI ID CHEBI:80658
Definition A retinoid obtained by epoxidation across the 5,6-double bond of retinoic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C20H28O3
Net Charge 0
Average Mass 316.435
Monoisotopic Mass 316.20384
InChI InChI=1S/C20H28O3/c1-15(8-6-9-16(2)14-17(21)22)10-13-20-18(3,4)11-7-12-19(20,5)23-20/h6,8-10,13-14H,7,11-12H2,1-5H3,(H,21,22)/b9-6+,13-10+,15-8+,16-14+
InChIKey KEEHJLBAOLGBJZ-WEDZBJJJSA-N
SMILES C12(C(CCCC1(C)O2)(C)C)/C=C/C(=C/C=C/C(=C/C(O)=O)/C)/C
Metabolite of Species Details
Rattus norvegicus (NCBI:txid10116) See: PubMed
Homo sapiens (NCBI:txid9606) See: PubMed
Roles Classification
Biological Role(s): human xenobiotic metabolite
Any human metabolite produced by metabolism of a xenobiotic compound in humans.
rat metabolite
Any mammalian metabolite produced during a metabolic reaction in rat (Rattus norvegicus).
EC 4.1.1.17 (ornithine decarboxylase) inhibitor
An EC 4.1.1.* (carboxy-lyase) inhibitor that interferes with the action of ornithine decarboxylase (EC 4.1.1.17).
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 5,6-epoxyretinoic acid (CHEBI:80658) has functional parent all-trans-retinoic acid (CHEBI:15367)
5,6-epoxyretinoic acid (CHEBI:80658) has role antineoplastic agent (CHEBI:35610)
5,6-epoxyretinoic acid (CHEBI:80658) has role EC 4.1.1.17 (ornithine decarboxylase) inhibitor (CHEBI:139556)
5,6-epoxyretinoic acid (CHEBI:80658) has role human xenobiotic metabolite (CHEBI:76967)
5,6-epoxyretinoic acid (CHEBI:80658) has role rat metabolite (CHEBI:86264)
5,6-epoxyretinoic acid (CHEBI:80658) is a epoxide (CHEBI:32955)
5,6-epoxyretinoic acid (CHEBI:80658) is a retinoid (CHEBI:26537)
5,6-epoxyretinoic acid (CHEBI:80658) is conjugate acid of 5,6-epoxyretinoate (CHEBI:139183)
Incoming 1-O-(5,6-epoxyretinoyl)-β-D-glucuronic acid (CHEBI:139558) has functional parent 5,6-epoxyretinoic acid (CHEBI:80658)
5,6-epoxyretinoate (CHEBI:139183) is conjugate base of 5,6-epoxyretinoic acid (CHEBI:80658)
IUPAC Name
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl)nona-2,4,6,8-tetraenoic acid
Synonym Source
all-trans-5,6-Epoxy-5,6-dihydroretinoic acid KEGG COMPOUND
Manual Xrefs Databases
C16680 KEGG COMPOUND
HMDB0012451 HMDB
LMPR01090055 LIPID MAPS
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Registry Numbers Types Sources
13100-69-1 CAS Registry Number ChemIDplus
1391567 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
12703967 PubMed citation Europe PMC
15606149 PubMed citation Europe PMC
1859380 PubMed citation Europe PMC
275830 PubMed citation Europe PMC
4091803 PubMed citation Europe PMC
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6256061 PubMed citation Europe PMC
6358966 PubMed citation Europe PMC
6942675 PubMed citation Europe PMC
7056740 PubMed citation Europe PMC
7082654 PubMed citation Europe PMC
7378063 PubMed citation Europe PMC
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7431123 PubMed citation Europe PMC
Last Modified
31 January 2018