(2S,3S,4S,5R,6R)-6-{2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl]-2-oxoethoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 164969
• Molecular Formular: C27H38O11
• Molecular Mass: 538.58402
• Monoisotopic Mass: 538.24141204
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@](CC2)(C(=O)CO[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)O)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2[C@@H](O)C[C@]2([C@H]1CC[C@]2(O)C(=O)CO[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)C)C
• InChI: InChI=1S/C27H38O11/c1-25-7-5-13(28)9-12(25)3-4-14-15-6-8-27(36,26(15,2)10-16(29)18(14)25)17(30)11-37-24-21(33)19(31)20(32)22(38-24)23(34)35/h9,14-16,18-22,24,29,31-33,36H,3-8,10-11H2,1-2H3,(H,34,35)/t14-,15-,16-,18+,19-,20-,21+,22-,24+,25-,26-,27-/m0/s1
• InChIKey: SXDBDFVHISOKJP-YXSMBZLISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-{2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]-2-oxoethoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-{2-[(1S,2R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl]-2-oxoethoxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (11β)-11,17-Dihydroxy-3,20-dioxopregn-4-en-21-yl β-D-Glucopyranosiduronic Acid; Cortisol Glucuronide; 21-(β-D-Glucopyranuronosyloxy)-11β,17-dihydroxy-pregn-4-ene-3,20-dione; 11β,17-Dihydroxy-3,20-dioxopregn-4-en-21-yl β-D-Glucopyranosiduronic Acid; Cortisol 21-Glucuronide; Cortisol 21-β-D-Glucuronide

Database IDs

• CAS Number: 7301-54-4
• PubChem SID: 162259103
• PubChem CID: 71314978

CALCULATED PROPERTIES

• Acid pKa: 3.1267018
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -2.521227
• LogD (pH = 7.4): -3.6328757
• Log P: -0.17539467
• Molar Refractivity: 129.6807 cm^3
• Polarizability: 51.965614 Å^3
• Polar Surface Area: 191.05 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C696315

Cortisol 21-β-D-Glucuronide is a phase II metabolite of Cortisol (H714615).

REFERENCES

• Spielgelhalder, B., et al.: J. Steroid Biochem., 7, 749 (1976)
• Vanluchene, E., et al.: J. Chromatogr., 456, 175 (1976)
• Choi, M., et al.: Steroids, 65, 54 (1976)