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all-trans-retinoic acid (CHEBI:15367)

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ChEBI Name all-trans-retinoic acid
ChEBI ID CHEBI:15367
ChEBI ASCII Name all-trans-retinoic acid
Definition A retinoic acid in which all four exocyclic double bonds have E- (trans-) geometry.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:8815, CHEBI:45376
Supplier Information
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Formula Source
C20H28O2 KEGG COMPOUND
Net Charge 0
Average Mass 300.43512
InChI
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+
InChIKey
SHGAZHPCJJPHSC-YCNIQYBTSA-N
SMILES
CC(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(C)=C/C(O)=O
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via retinoic acid )
signalling molecule
A molecular messenger in which the molecule is specifically involved in transmitting information between cells. Such molecules are released from the cell sending the signal, cross over the gap between cells by diffusion, and interact with specific receptors in another cell, triggering a response in that cell by activating a series of enzyme controlled reactions which lead to changes inside the cell.
retinoid X receptor agonist
An agonist that selectively binds to and activates a retinoid X receptor.
AP-1 antagonist
An antogonist that interferes with the action of activator protein 1 (AP-1).
retinoic acid receptor agonist
An agonist that selectively binds to and activates a retinoic acid receptor.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
keratolytic drug
A drug that softens, separates, and causes desquamation of the cornified epithelium or horny layer of skin. Keratolytic drugs are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases.
anti-inflammatory agent
Any compound that has anti-inflammatory effects.
View more on the ChEBI Ontology
ChEBI Ontology
Outgoing all-trans-retinoic acid (CHEBI:15367) has role anti-inflammatory agent (CHEBI:67079)
all-trans-retinoic acid (CHEBI:15367) has role antineoplastic agent (CHEBI:35610)
all-trans-retinoic acid (CHEBI:15367) has role antioxidant (CHEBI:22586)
all-trans-retinoic acid (CHEBI:15367) has role AP-1 antagonist (CHEBI:67199)
all-trans-retinoic acid (CHEBI:15367) has role human metabolite (CHEBI:77746)
all-trans-retinoic acid (CHEBI:15367) has role keratolytic drug (CHEBI:50176)
all-trans-retinoic acid (CHEBI:15367) has role retinoic acid receptor agonist (CHEBI:67198)
all-trans-retinoic acid (CHEBI:15367) has role retinoid X receptor agonist (CHEBI:63794)
all-trans-retinoic acid (CHEBI:15367) has role signalling molecule (CHEBI:62488)
all-trans-retinoic acid (CHEBI:15367) is a retinoic acid (CHEBI:26536)
all-trans-retinoic acid (CHEBI:15367) is conjugate acid of all-trans-retinoate (CHEBI:35291)
Incoming 1-O-all-trans-retinoyl-β-glucuronic acid (CHEBI:28870) has functional parent all-trans-retinoic acid (CHEBI:15367)
4-hydroxyphenyl retinamide (CHEBI:42588) has functional parent all-trans-retinoic acid (CHEBI:15367)
all-trans-4-hydroxyretinoic acid (CHEBI:63795) has functional parent all-trans-retinoic acid (CHEBI:15367)
vitamin A (CHEBI:12777) has part all-trans-retinoic acid (CHEBI:15367)
all-trans-retinoate (CHEBI:35291) is conjugate base of all-trans-retinoic acid (CHEBI:15367)
IUPAC Name
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid
Synonyms Sources
(all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid KEGG COMPOUND
3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ECL) KEGG COMPOUND
Acide retinoique (French) (DSL) KEGG COMPOUND
AGN 100335 KEGG COMPOUND
all-(E)-Retinoic acid KEGG COMPOUND
all-trans-beta-Retinoic acid KEGG COMPOUND
all-trans-Retinoic acid KEGG COMPOUND
all-trans-Tretinoin KEGG COMPOUND
all-trans-Vitamin A acid KEGG COMPOUND
all-trans-Vitamin A1 acid KEGG COMPOUND
beta-Retinoic acid KEGG COMPOUND
RETINOIC ACID PDBeChem
Retinoic acid KEGG COMPOUND
Ro 1-5488 KEGG COMPOUND
trans-Retinoic acid KEGG COMPOUND
Tretin M KEGG COMPOUND
tretinoin ChemIDplus
Tretinoine (French) (EINECS) KEGG COMPOUND
Vitamin A acid KEGG COMPOUND
Brand Names Sources
Eudyna Deprecated term DrugBank
Renova DrugBank
Retin-A DrugBank
Retisol-A DrugBank
Solage Deprecated term DrugBank
Stieva-A DrugBank
Vesanoid DrugBank
Vitinoin Deprecated term DrugBank
Database Links Databases
C00777 KEGG COMPOUND
D00094 KEGG DRUG
DB00755 DrugBank
HMDB01852 HMDB
LMPR01090019 LIPID MAPS
REA PDBeChem
Tretinoin Wikipedia
View more database links
Registry Numbers Types Sources
2057223 Beilstein Registry Number Beilstein
2057223 Reaxys Registry Number Reaxys
302-79-4 CAS Registry Number KEGG COMPOUND
302-79-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
30 January 2014

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