(2S,3S,4S,5R,6S)-6-{[(2Z,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

• ChemBase ID: 177463
• Molecular Formular: C26H36O8
• Molecular Mass: 476.55924
• Monoisotopic Mass: 476.24101811
• SMILES: C1(CCCC(=C1/C=C/C(=C/C=C/C(=C\C(=O)O[C@@H]1O[C@H]([C@@H](O)[C@H](O)[C@@H]1O)C(=O)O)/C)/C)C)(C)C
• Canonical SMILES: O=C(O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)/C=C(\C=C\C=C(\C=C\C1=C(C)CCCC1(C)C)/C)/C
• 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
• InChIKey: MTGFYEHKPMOVNE-SMOSQNLZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[(2Z,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
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[(2Z,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
• Synonyms: 13-cis-Retinoic Acid β-D-Glucopyranuronic Acid; β-D-Glucopyranuronic Acid, 1-(13-cis-Retinoate); 13-cis Retinoyl β-D-Glucuronide, >85% By HPLC

Database IDs

• CAS Number: 78147-42-9
• PubChem SID: 164233373
• PubChem CID: 10600672

CALCULATED PROPERTIES

• Acid pKa: 3.38921
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 1.202019
• LogD (pH = 7.4): -0.10571694
• Log P: 3.2999074
• Molar Refractivity: 130.0894 cm^3
• Polarizability: 49.822422 Å^3
• Polar Surface Area: 133.52 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - R253520

A metabolite of 13-cis-Retinoic acid.

REFERENCES

• Dunagin, P.E., et al.: Science, 148, 86 (1965)
• Lippel, K., et al.: J. Lipid Res., 9, 168 (1965)