CHEBI:15367 - all-trans-retinoic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
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:45376, CHEBI:8815
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Formula C20H28O2
Net Charge 0
Average Mass 300.43512
Monoisotopic Mass 300.20893
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
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) Found in blood (UBERON:0000178). See: Geigy Scientific Tables, 8th Rev edition, pp. 165-177. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp., Basel, Switzerland c1981-1992.
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
(via retinoic acid )
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via vitamin A )
fat-soluble vitamin (role)
Any vitamin that dissolves in fats and are stored in body tissues. Unlike the water-soluble vitamins, they are stored in the body for long periods of time and generally pose a greater risk for toxicity when consumed in excess.
(via vitamin A )
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.
retinoic acid receptor agonist
An agonist that selectively binds to and activates a retinoic acid receptor.
View more via 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 a vitamin A (CHEBI:12777)
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)
5,6-epoxyretinoic acid (CHEBI:80658) has functional parent all-trans-retinoic acid (CHEBI:15367)
all-trans-13,14-dihydroretinoic acid (CHEBI:194189) has functional parent all-trans-retinoic acid (CHEBI:15367)
all-trans-16-hydroxyretinoic acid (CHEBI:139256) has functional parent all-trans-retinoic acid (CHEBI:15367)
all-trans-18-hydroxyretinoic acid (CHEBI:80657) has functional parent all-trans-retinoic acid (CHEBI:15367)
all-trans-3,4-didehydroretinoic acid (CHEBI:133794) has functional parent all-trans-retinoic acid (CHEBI:15367)
all-trans-4,16-dihydroxyretinoic acid (CHEBI:139259) has functional parent all-trans-retinoic acid (CHEBI:15367)
all-trans-4,18-dihydroxyretinoic acid (CHEBI:139261) 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)
all-trans-4-oxo-16-hydroxyretinoic acid (CHEBI:139263) has functional parent all-trans-retinoic acid (CHEBI:15367)
all-trans-4-oxo-18-hydroxyretinoic acid (CHEBI:139265) has functional parent all-trans-retinoic acid (CHEBI:15367)
all-trans-4-oxoretinoic acid (CHEBI:80656) has functional parent all-trans-retinoic acid (CHEBI:15367)
SR11302 (CHEBI:197438) has functional parent 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
INNs Sources
tretinoin WHO MedNet
tretinoína WHO MedNet
trétinoïne WHO MedNet
tretinoinum WHO MedNet
Synonyms Sources
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid ChEBI
(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 KEGG COMPOUND
3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-all-trans-tetraenoic acid ChemIDplus
3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2E,4E,6E,8E-tetraenoic acid LIPID MAPS
Acide retinoique (French) KEGG COMPOUND
AGN 100335 KEGG COMPOUND
all-(E)-retinoic acid KEGG COMPOUND
all-trans retinoic acid ChemIDplus
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 KEGG COMPOUND
Ro 1-5488 KEGG COMPOUND
trans-retinoic acid KEGG COMPOUND
Tretin M KEGG COMPOUND
vitamin A acid KEGG COMPOUND
Brand Names Sources
Altreno DrugBank
Atralin ChemIDplus
Avita ChemIDplus
Betarretin ChemIDplus
Biacna DrugBank
Cordes vas ChemIDplus
Dermairol ChemIDplus
Refissa ChemIDplus
Renova DrugBank
Retin-A DrugBank
Retisol-A DrugBank
Stieva-A DrugBank
Tri-luma DrugBank
Veltin DrugBank
Vesanoid DrugBank
Vitinoin Deprecated term DrugBank
Manual Xrefs Databases
2722 DrugCentral
C00777 KEGG COMPOUND
D00094 KEGG DRUG
DB00755 DrugBank
FDB022710 FooDB
HMDB0001852 HMDB
LMPR01090019 LIPID MAPS
REA PDBeChem
Retinoic_acid Wikipedia
Tretinoin Wikipedia
View more database links
Registry Numbers Types Sources
2057223 Reaxys Registry Number Reaxys
2057223 Beilstein Registry Number Beilstein
302-79-4 CAS Registry Number KEGG COMPOUND
302-79-4 CAS Registry Number ChemIDplus
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Last Modified
13 October 2023