1.0 2011-09-21 00:24:52 UTC 2015-07-21 06:57:31 UTC FDB023112 Retinoyl beta-glucuronide Retinoyl beta-glucuronide is a naturally occurring, biologically active metabolite of vitamin A. Although retinoyl beta-glucuronide is regarded as a detoxification product of retinoic acid, it plays several roles in the functions of vitamin A. It can serve as a source of retinoic acid, and it may be a vehicle for transport of retinoic acid to target tissues. Topically applied retinoyl beta-glucuronide is comparable in efficacy to retinoic acid in the treatment of acne in humans, without the same side effects. Retinoyl beta-glucuronide may or may not be teratogenic, depending on the mode of administration and the species in which it is used. It may be a valuable therapeutic compound for the treatment of skin disorders and certain types of cancers. [HMDB] 13-cis-Retinoate 13-cis-Retinoic acid 13-cis-retinoic acid acyl beta-D-glucuronide 13-cis-retinoic acid acyl beta-delta-glucuronide 13-cis-Retinoyl glucuronide 13-cis-retinoyl-beta-D-glucuronide 13-cis-retinoyl-beta-delta-glucuronide 13-cis-retinoyl-beta-glucuronide 9-cis-Retinoyl-beta-D-glucuronide 9-cis-Retinoyl-beta-delta-glucuronide all-trans-Retinoyl-b-glucuronide all-trans-Retinoyl-beta-D-glucuronide all-trans-Retinoyl-beta-delta-glucuronide all-trans-Retinoyl-beta-glucuronide all-trans-Retinoyl-β-glucuronide Glucuronide Retinoic acid beta-D-glucuronide Retinoic acid beta-delta-glucuronide Retinoyl b-glucuronide Retinoyl beta-glucuronide Retinoyl glucuronide Retinoyl-beta-glucuronide C26H36O8 476.5592 476.241018128 (2S,3S,4S,5R,6S)-6-{[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid glucuronide 401-10-5 O[C@@H]1[C@@H](O)[C@@H](O[C@H](C(O)=O)[C@H]1O)OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C InChI=1S/C26H36O8/c1-15(11-12-18-17(3)10-7-13-26(18,4)5)8-6-9-16(2)14-19(27)33-25-22(30)20(28)21(29)23(34-25)24(31)32/h6,8-9,11-12,14,20-23,25,28-30H,7,10,13H2,1-5H3,(H,31,32)/b9-6+,12-11+,15-8+,16-14+/t20-,21-,22+,23-,25+/m0/s1 MTGFYEHKPMOVNE-NEFMKCFNSA-N belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. Diterpene glycosides Organic compounds Lipids and lipid-like molecules Prenol lipids Terpene glycosides Aliphatic heteromonocyclic compounds Acetals Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Diterpenoids Enoate esters Fatty acid esters Hexoses Hydrocarbon derivatives O-glucuronides Organic oxides Oxacyclic compounds Oxanes Polyols Pyrans Retinoid esters Secondary alcohols 1-o-glucuronide Acetal Alcohol Aliphatic heteromonocyclic compound Alpha,beta-unsaturated carboxylic ester Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Dicarboxylic acid or derivatives Diterpene glycoside Diterpenoid Enoate ester Fatty acid ester Fatty acyl Glucuronic acid or derivatives Hexose monosaccharide Hydrocarbon derivative Hydroxy acid Monosaccharide O-glucuronide Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxane Polyol Pyran Retinoid ester Retinoid skeleton Secondary alcohol glucuronic acids Solid logp 3.57 ALOGPS logs -4.01 ALOGPS solubility 4.63e-02 g/l ALOGPS logp 3.3 ChemAxon pka_strongest_acidic 3.39 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2S,3S,4S,5R,6S)-6-{[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid ChemAxon average_mass 476.5592 ChemAxon mono_mass 476.241018128 ChemAxon smiles O[C@@H]1[C@@H](O)[C@@H](O[C@H](C(O)=O)[C@H]1O)OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C ChemAxon formula C26H36O8 ChemAxon inchi InChI=1S/C26H36O8/c1-15(11-12-18-17(3)10-7-13-26(18,4)5)8-6-9-16(2)14-19(27)33-25-22(30)20(28)21(29)23(34-25)24(31)32/h6,8-9,11-12,14,20-23,25,28-30H,7,10,13H2,1-5H3,(H,31,32)/b9-6+,12-11+,15-8+,16-14+/t20-,21-,22+,23-,25+/m0/s1 ChemAxon inchikey MTGFYEHKPMOVNE-NEFMKCFNSA-N ChemAxon polar_surface_area 133.52 ChemAxon refractivity 130.09 ChemAxon polarizability 51.85 ChemAxon rotatable_bond_count 8 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Retinol Metabolism SMP00074 map00830 Specdb::CMs 25412 Specdb::CMs 38530 Specdb::CMs 175429 Specdb::MsMs 65655 Specdb::MsMs 65656 Specdb::MsMs 65657 Specdb::MsMs 123081 Specdb::MsMs 123082 Specdb::MsMs 123083 Specdb::MsMs 2677572 Specdb::MsMs 2677573 Specdb::MsMs 2677574 Specdb::MsMs 3030677 Specdb::MsMs 3030678 Specdb::MsMs 3030679 HMDB03141 #<Reference:0x000055ce307a1148> #<Reference:0x000055ce307a0f90> #<Reference:0x000055ce307a0d10> #<Reference:0x000055ce307a0b58> #<Reference:0x000055ce307a09a0> #<Reference:0x000055ce307a0798> #<Reference:0x000055ce307a0590> #<Reference:0x000055ce307a03d8> #<Reference:0x000055ce307a01f8> #<Reference:0x000055ce307a7f98> #<Reference:0x000055ce307a7db8> #<Reference:0x000055ce307a7b88> #<Reference:0x000055ce307a7958> #<Reference:0x000055ce307a7728> #<Reference:0x000055ce307a7408> #<Reference:0x000055ce307a7200> #<Reference:0x000055ce307a7048> #<Reference:0x000055ce307a6e90> #<Reference:0x000055ce307a6cd8> #<Reference:0x000055ce307a6af8> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Beta-glucuronidase P08236 GUSB 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