1.0 2011-09-21 00:18:18 UTC 2015-10-09 22:30:58 UTC FDB022710 Retinoic acid Retinoic acid is the oxidized form of Vitamin A. It functions in determining position along embryonic anterior/posterior axis in chordates. It acts through Hox genes, which ultimately controls anterior/posterior patterning in early developmental stages (PMID: 17495912). It is an important regulator of gene expression during growth and development, and in neoplasms. Tretinoin, also known as retinoic acid and derived from maternal vitamin A, is essential for normal growth and embryonic development. An excess of tretinoin can be teratogenic. It is used in the treatment of psoriasis; acne vulgaris; and several other skin diseases. It has also been approved for use in promyelocytic leukemia (leukemia, promyelocytic, acute). [HMDB] (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoate (ecl) 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic acid (ecl) acide retinoique (French) AGN 100335 all-(E)-Retinoate all-(E)-Retinoic acid all-trans-Retinoate all-trans-Retinoic acid all-trans-Tretinoin all-trans-Vitamin a acid all-trans-Vitamin A1 acid all-trans-β-retinoate all-trans-β-retinoic acid beta-Retinoate beta-Retinoic acid Retinoate Retisol-a Ro 1-5488 Solage Stieva-a trans-Retinoate trans-Retinoic acid Tretin M Tretinoine (French) Vitamin A acid Vitinoin β-retinoate β-retinoic acid C20H28O2 300.4351 300.20893014 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid isotretinoin 302-79-4 CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC(O)=O 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) SHGAZHPCJJPHSC-UHFFFAOYSA-N belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. Retinoids Organic compounds Lipids and lipid-like molecules Prenol lipids Retinoids Aliphatic homomonocyclic compounds Carbonyl compounds Carboxylic acids Diterpenoids Hydrocarbon derivatives Medium-chain fatty acids Methyl-branched fatty acids Monocarboxylic acids and derivatives Organic oxides Unsaturated fatty acids Aliphatic homomonocyclic compound Branched fatty acid Carbonyl group Carboxylic acid Carboxylic acid derivative Diterpenoid Fatty acid Fatty acyl Hydrocarbon derivative Medium-chain fatty acid Methyl-branched fatty acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Retinoic acid Retinoid skeleton Unsaturated fatty acid alpha,beta-unsaturated monocarboxylic acid retinoid Solid logp 5.66 ALOGPS logs -4.80 ALOGPS solubility 4.77e-03 g/l ALOGPS logp 5.01 ChemAxon pka_strongest_acidic 5 ChemAxon iupac 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid ChemAxon average_mass 300.4351 ChemAxon mono_mass 300.20893014 ChemAxon smiles CC(C=CC1=C(C)CCCC1(C)C)=CC=CC(C)=CC(O)=O ChemAxon formula C20H28O2 ChemAxon 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) ChemAxon inchikey SHGAZHPCJJPHSC-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 97.79 ChemAxon polarizability 36.93 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 7235 Specdb::CMs 38146 Specdb::CMs 117959 Specdb::CMs 809298 Specdb::MsMs 252453 Specdb::MsMs 252454 Specdb::MsMs 252455 Specdb::MsMs 272394 Specdb::MsMs 272395 Specdb::MsMs 272396 Specdb::MsMs 3395149 Specdb::MsMs 3395150 Specdb::MsMs 3395151 Specdb::MsMs 3395152 Specdb::MsMs 3395153 Specdb::MsMs 3395154 HMDB01852 REA #<Reference:0x000055ce30530f08> #<Reference:0x000055ce30530c88> #<Reference:0x000055ce30530ad0> #<Reference:0x000055ce30530918> #<Reference:0x000055ce30530760> #<Reference:0x000055ce305305a8> #<Reference:0x000055ce305303f0> #<Reference:0x000055ce30530238> #<Reference:0x000055ce30530080> #<Reference:0x000055ce3052fe78> #<Reference:0x000055ce3052fc20> #<Reference:0x000055ce3052f928> #<Reference:0x000055ce3052f748> #<Reference:0x000055ce3052f590> #<Reference:0x000055ce3052f3d8> #<Reference:0x000055ce3052f220> #<Reference:0x000055ce3052f068> #<Reference:0x000055ce3052eeb0> Cytochrome P450 2D6 Q6NWU0 CYP2D6 Cytochrome P450, family 1, subfamily A, polypeptide 1 A0N0X8 CYP1A1 Retinoic acid receptor alpha P10276 RARA Retinoic acid receptor beta P10826 RARB Retinoic acid receptor gamma P13631 RARG Retinoic acid receptor responder protein 1 P49788 RARRES1 Retinoic acid receptor RXR-alpha P19793 RXRA Retinoic acid receptor RXR-beta P28702 RXRB Retinoic acid receptor RXR-gamma P48443 RXRG UDP-glucuronosyltransferase 1-1 P22309 UGT1A1 UDP-glucuronosyltransferase 1-10 Q9HAW8 UGT1A10 UDP-glucuronosyltransferase 1-3 P35503 UGT1A3 UDP-glucuronosyltransferase 1-4 P22310 UGT1A4 UDP-glucuronosyltransferase 1-5 P35504 UGT1A5 UDP-glucuronosyltransferase 1-6 P19224 UGT1A6 UDP-glucuronosyltransferase 1-7 Q9HAW7 UGT1A7 UDP-glucuronosyltransferase 1-8 Q9HAW9 UGT1A8 UDP-glucuronosyltransferase 1-9 O60656 UGT1A9 UDP-glucuronosyltransferase 2A1 Q9Y4X1 UGT2A1 UDP-glucuronosyltransferase 2A3 Q6UWM9 UGT2A3 UDP-glucuronosyltransferase 2B10 P36537 UGT2B10 UDP-glucuronosyltransferase 2B11 O75310 UGT2B11 UDP-glucuronosyltransferase 2B15 P54855 UGT2B15 UDP-glucuronosyltransferase 2B17 O75795 UGT2B17 UDP-glucuronosyltransferase 2B28 Q9BY64 UGT2B28 UDP-glucuronosyltransferase 2B4 P06133 UGT2B4 UDP-glucuronosyltransferase 2B7 P16662 UGT2B7