Retinoyl b-glucuronide (CHEM022524)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:38:31 UTC
Update Date2016-11-09 01:17:31 UTC
Accession NumberCHEM022524
Identification
Common NameRetinoyl b-glucuronide
ClassSmall Molecule
DescriptionA retinoid that is retinoic acid in which the carboxy proton has been replaced by a beta-D-glucuronyl residue.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
all-trans-Retinoyl-beta-glucuronideChEBI
Retinoyl glucuronideChEBI
all-trans-Retinoyl-b-glucuronideGenerator
all-trans-Retinoyl-β-glucuronideGenerator
13-cis-RetinoateHMDB
13-cis-Retinoic acidHMDB
13-cis-Retinoic acid acyl beta-D-glucuronideHMDB
13-cis-Retinoic acid acyl beta-delta-glucuronideHMDB
13-cis-Retinoyl glucuronideHMDB
13-cis-Retinoyl-beta-D-glucuronideHMDB
13-cis-Retinoyl-beta-delta-glucuronideHMDB
13-cis-Retinoyl-beta-glucuronideHMDB
9-cis-Retinoyl-beta-D-glucuronideHMDB
9-cis-Retinoyl-beta-delta-glucuronideHMDB
all-trans-Retinoyl-beta-D-glucuronideHMDB
all-trans-Retinoyl-beta-delta-glucuronideHMDB
GlucuronideHMDB
RetinoateHMDB
Retinoic acidHMDB
Retinoic acid beta-D-glucuronideHMDB
Retinoic acid beta-delta-glucuronideHMDB
Retinoyl beta-glucuronideHMDB
Retinoyl-beta-glucuronideHMDB
trans-Retinoyl glucuronideMeSH, HMDB
Chemical FormulaC26H36O8
Average Molecular Mass476.559 g/mol
Monoisotopic Mass476.241 g/mol
CAS Registry Number401-10-5
IUPAC Name(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
Traditional Nameglucuronide
SMILESO[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 IdentifierInChI=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
InChI KeyMTGFYEHKPMOVNE-NEFMKCFNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentDiterpene glycosides
Alternative Parents
Substituents
  • Diterpene glycoside
  • Retinoid ester
  • Diterpenoid
  • Retinoid skeleton
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Beta-hydroxy acid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Acetal
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
logP3.57ALOGPS
logP3.3ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity130.09 m³·mol⁻¹ChemAxon
Polarizability51.85 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9432400000-25dd7257fa97ce57c686Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004i-3051009000-fd7898490f7303f898ccSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ke9-0693400000-31eed182f08fe6786169Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052u-0891000000-ca789901418c22bb0493Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1920000000-e38e08d95bad4a423551Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1190200000-9141a0351cb4c8689ff4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-3690100000-f02b84b6d3b8cceeb6cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0535-8590000000-12eae5811075d2fce9f9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-057r-0565900000-0aac4f4c541ab0976b56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-009f-0923100000-bb8c1ba6dc7f05b15be7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ac0-2900000000-b37fb8c36dde85ab4488Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-0390700000-eddabec40f40511d435fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6s-2391400000-4b33ff2150a642a78136Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0r01-3390000000-158c7d14c4f6713d87daSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003141
FooDB IDFDB023112
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID2304843
BioCyc IDNot Available
METLIN ID2280
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4445170
ChEBI ID28870
PubChem Compound ID5281877
Kegg Compound IDC11061
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14690762
2. Ghosal A, Yuan Y, Hapangama N, Su AD, Alvarez N, Chowdhury SK, Alton KB, Patrick JE, Zbaida S: Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of 3-hydroxydesloratadine. Biopharm Drug Dispos. 2004 Sep;25(6):243-52.
3. Brunelle FM, Verbeeck RK: Glucuronidation of diflunisal in liver and kidney microsomes of rat and man. Xenobiotica. 1996 Feb;26(2):123-31.
4. Niles RM, Cook CP, Meadows GG, Fu YM, McLaughlin JL, Rankin GO: Resveratrol is rapidly metabolized in athymic (nu/nu) mice and does not inhibit human melanoma xenograft tumor growth. J Nutr. 2006 Oct;136(10):2542-6.
5. Sass JO, Masgrau E, Saurat JH, Nau H: Metabolism of oral 9-cis-retinoic acid in the human. Identification of 9-cis-retinoyl-beta-glucuronide and 9-cis-4-oxo-retinoyl-beta-glucuronide as urinary metabolites. Drug Metab Dispos. 1995 Sep;23(9):887-91.
6. Calabrese CR, Loadman PM, Lim LS, Bibby MC, Double JA, Brown JE, Lamb JH: In vivo metabolism of the antitumor imidazoacridinone C1311 in the mouse and in vitro comparison with humans. Drug Metab Dispos. 1999 Feb;27(2):240-5.
7. Yamanaka H, Nakajima M, Katoh M, Kanoh A, Tamura O, Ishibashi H, Yokoi T: Trans-3'-hydroxycotinine O- and N-glucuronidations in human liver microsomes. Drug Metab Dispos. 2005 Jan;33(1):23-30. Epub 2004 Oct 6.
8. Sperker B, Murdter TE, Schick M, Eckhardt K, Bosslet K, Kroemer HK: Interindividual variability in expression and activity of human beta-glucuronidase in liver and kidney: consequences for drug metabolism. J Pharmacol Exp Ther. 1997 May;281(2):914-20.
9. Kosoglou T, Statkevich P, Johnson-Levonas AO, Paolini JF, Bergman AJ, Alton KB: Ezetimibe: a review of its metabolism, pharmacokinetics and drug interactions. Clin Pharmacokinet. 2005;44(5):467-94.
10. Moss T, Howes D, Williams FM: Percutaneous penetration and dermal metabolism of triclosan (2,4, 4'-trichloro-2'-hydroxydiphenyl ether). Food Chem Toxicol. 2000 Apr;38(4):361-70.
11. Kochansky CJ, Xia YQ, Wang S, Cato B, Creighton M, Vincent SH, Franklin RB, Reed JR: Species differences in the elimination of a peroxisome proliferator-activated receptor agonist highlighted by oxidative metabolism of its acyl glucuronide. Drug Metab Dispos. 2005 Dec;33(12):1894-904. Epub 2005 Sep 23.
12. Cunha PD, Lord RS, Johnson ST, Wilker PR, Aster RH, Bougie DW: Immune hemolytic anemia caused by sensitivity to a metabolite of etodolac, a nonsteroidal anti-inflammatory drug. Transfusion. 2000 Jun;40(6):663-8.
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14. Johnson AG, Rigby RJ, Taylor PJ, Jones CE, Allen J, Franzen K, Falk MC, Nicol D: The kinetics of mycophenolic acid and its glucuronide metabolite in adult kidney transplant recipients. Clin Pharmacol Ther. 1999 Nov;66(5):492-500.
15. Oswald S, Haenisch S, Fricke C, Sudhop T, Remmler C, Giessmann T, Jedlitschky G, Adam U, Dazert E, Warzok R, Wacke W, Cascorbi I, Kroemer HK, Weitschies W, von Bergmann K, Siegmund W: Intestinal expression of P-glycoprotein (ABCB1), multidrug resistance associated protein 2 (ABCC2), and uridine diphosphate-glucuronosyltransferase 1A1 predicts the disposition and modulates the effects of the cholesterol absorption inhibitor ezetimibe in humans. Clin Pharmacol Ther. 2006 Mar;79(3):206-17. Epub 2006 Feb 7.
16. Kenny JR, Maggs JL, Tettey JN, Harrell AW, Parker SG, Clarke SE, Park BK: Formation and protein binding of the acyl glucuronide of a leukotriene B4 antagonist (SB-209247): relation to species differences in hepatotoxicity. Drug Metab Dispos. 2005 Feb;33(2):271-81. Epub 2004 Nov 2.
17. Qiao GL, Williams PL, Riviere JE: Percutaneous absorption, biotransformation, and systemic disposition of parathion in vivo in swine. I. Comprehensive pharmacokinetic model. Drug Metab Dispos. 1994 May-Jun;22(3):459-71.
18. Matsushima S, Maeda K, Kondo C, Hirano M, Sasaki M, Suzuki H, Sugiyama Y: Identification of the hepatic efflux transporters of organic anions using double-transfected Madin-Darby canine kidney II cells expressing human organic anion-transporting polypeptide 1B1 (OATP1B1)/multidrug resistance-associated protein 2, OATP1B1/multidrug resistance 1, and OATP1B1/breast cancer resistance protein. J Pharmacol Exp Ther. 2005 Sep;314(3):1059-67. Epub 2005 May 18.
19. Ethell BT, Riedel J, Englert H, Jantz H, Oekonomopulos R, Burchell B: Glucuronidation of HMR1098 in human microsomes: evidence for the involvement of UGT1A1 in the formation of S-glucuronides. Drug Metab Dispos. 2003 Aug;31(8):1027-34.
20. Andersen A: Final report on the safety assessment of sodium p-chloro-m-cresol, p-chloro-m-cresol, chlorothymol, mixed cresols, m-cresol, o-cresol, p-cresol, isopropyl cresols, thymol, o-cymen-5-ol, and carvacrol. Int J Toxicol. 2006;25 Suppl 1:29-127.
21. Sallustio BC, Sabordo L, Evans AM, Nation RL: Hepatic disposition of electrophilic acyl glucuronide conjugates. Curr Drug Metab. 2000 Sep;1(2):163-80.