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CHEBI:15367 - all-trans-retinoic acid
| Formula | C20H28O2 |
| Net Charge | 0 |
| Average Mass | 300.442 |
| Monoisotopic Mass | 300.20893 |
| SMILES | CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)C(C)(C)CCC1 |
| 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 |
| Wikipedia |
|---|
| Species of Metabolite | Component | Source | Comments |
|---|---|---|---|
| Homo sapiens (ncbitaxon:9606) | blood (UBERON:0000178) | Article (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 Roles: | 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 (Brønsted base). Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Brønsted base). |
| Biological Roles: | 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). retinoid X receptor agonist An agonist that selectively binds to and activates a retinoid X receptor. 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. 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. metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens). |
| Applications: | anti-inflammatory agent Any compound that has anti-inflammatory effects. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms. retinoic acid receptor agonist An agonist that selectively binds to and activates a retinoic acid receptor. 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. |
| ChEBI Ontology |
|---|
| Outgoing Relation(s) |
| 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 Relation(s) |
| all-trans-13,14-dihydroretinoic acid (CHEBI:194189) 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) |
| 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-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-4,16-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) |
| 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) |
| 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 | Source |
|---|---|
| tretinoína | WHO MedNet |
| tretinoin | WHO MedNet |
| trétinoïne | WHO MedNet |
| tretinoinum | WHO MedNet |
| Synonyms | Source |
|---|---|
| retinoic acid | KEGG COMPOUND |
| vitamin A acid | KEGG COMPOUND |
| Acide retinoique (French) | KEGG COMPOUND |
| 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid | KEGG COMPOUND |
| (all-E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid | KEGG COMPOUND |
| AGN 100335 | KEGG COMPOUND |
| Brand Names | Source |
|---|---|
| Altreno | DrugBank |
| Biacna | DrugBank |
| Vesanoid | DrugBank |
| Retin-A | DrugBank |
| Renova | DrugBank |
| Veltin | DrugBank |
| Manual Xrefs | Databases |
|---|---|
| C00777 | KEGG COMPOUND |
| REA | PDBeChem |
| DB00755 | DrugBank |
| LMPR01090019 | LIPID MAPS |
| Tretinoin | Wikipedia |
| D00094 | KEGG DRUG |
| HMDB0001852 | HMDB |
| Retinoic_acid | Wikipedia |
| 2722 | DrugCentral |
| FDB022710 | FooDB |
| Registry Numbers | Sources |
|---|---|
| Reaxys:2057223 | Reaxys |
| CAS:302-79-4 | KEGG COMPOUND |
| CAS:302-79-4 | ChemIDplus |
| Citations |
|---|