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
Supplier Information
Download Molfile XML SDF
more structures >>
Wikipedia License
Waiting for wikipedia content
Read full article at Wikipedia
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
302-79-4 CAS Registry Number KEGG COMPOUND
302-79-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10022884 PubMed citation Europe PMC
10970886 PubMed citation Europe PMC
11073974 PubMed citation Europe PMC
11214352 PubMed citation Europe PMC
11332619 PubMed citation Europe PMC
11343416 PubMed citation Europe PMC
11437362 PubMed citation Europe PMC
11556813 PubMed citation Europe PMC
11722649 PubMed citation Europe PMC
11896294 PubMed citation Europe PMC
11904404 PubMed citation Europe PMC
12958591 PubMed citation Europe PMC
14581379 PubMed citation Europe PMC
14605492 PubMed citation Europe PMC
14627725 PubMed citation Europe PMC
14704332 PubMed citation Europe PMC
14705145 PubMed citation Europe PMC
14978018 PubMed citation Europe PMC
15194426 PubMed citation Europe PMC
15318809 PubMed citation Europe PMC
15327395 PubMed citation Europe PMC
15359008 PubMed citation Europe PMC
15376324 PubMed citation Europe PMC
15476854 PubMed citation Europe PMC
15537748 PubMed citation Europe PMC
15539337 PubMed citation Europe PMC
15675886 PubMed citation Europe PMC
15839997 PubMed citation Europe PMC
16569247 PubMed citation Europe PMC
16685080 PubMed citation Europe PMC
16688769 PubMed citation Europe PMC
16720557 PubMed citation Europe PMC
16819260 PubMed citation Europe PMC
16847436 PubMed citation Europe PMC
16920920 PubMed citation Europe PMC
17073551 PubMed citation Europe PMC
17166212 PubMed citation Europe PMC
17204142 PubMed citation Europe PMC
17447762 PubMed citation Europe PMC
18052213 PubMed citation Europe PMC
18085670 PubMed citation Europe PMC
18162363 PubMed citation Europe PMC
18183617 PubMed citation Europe PMC
18318655 PubMed citation Europe PMC
18322276 PubMed citation Europe PMC
18400206 PubMed citation Europe PMC
18404486 PubMed citation Europe PMC
18440196 PubMed citation Europe PMC
18678272 PubMed citation Europe PMC
18800767 PubMed citation Europe PMC
18819820 PubMed citation Europe PMC
18977311 PubMed citation Europe PMC
19018099 PubMed citation Europe PMC
19112091 PubMed citation Europe PMC
19144697 PubMed citation Europe PMC
19427305 PubMed citation Europe PMC
19587328 PubMed citation Europe PMC
19597529 PubMed citation Europe PMC
19814868 PubMed citation Europe PMC
19841174 PubMed citation Europe PMC
21898109 PubMed citation Europe PMC
21924320 PubMed citation Europe PMC
21993673 PubMed citation Europe PMC
22134377 PubMed citation Europe PMC
22177959 PubMed citation Europe PMC
22180426 PubMed citation Europe PMC
22244299 PubMed citation Europe PMC
22261335 PubMed citation Europe PMC
22428994 PubMed citation Europe PMC
22514600 PubMed citation Europe PMC
22532966 PubMed citation Europe PMC
22534100 PubMed citation Europe PMC
22538278 PubMed citation Europe PMC
22741806 PubMed citation Europe PMC
27759097 PubMed citation Europe PMC
29492455 PubMed citation Europe PMC
33662750 PubMed citation Europe PMC
33820492 PubMed citation Europe PMC
34050114 PubMed citation Europe PMC
34050360 PubMed citation Europe PMC
34091189 PubMed citation Europe PMC
7501014 PubMed citation Europe PMC
7704533 PubMed citation Europe PMC
7961949 PubMed citation Europe PMC
Last Modified
13 October 2023