methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.02,7.011,15]heptadecan-5-yl]oxy}oxane-2-carboxylate

• ChemBase ID: 160641
• Molecular Formular: C32H46O11
• Molecular Mass: 606.70104
• Monoisotopic Mass: 606.30401229
• SMILES: C1[C@H](C[C@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C(=O)CC2)C)C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](O[C@@H]2CC[C@]3([C@H](C2)CC[C@@H]2[C@@H]3CC[C@]3([C@H]2CCC3=O)C)C)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C32H46O11/c1-16(33)39-25-26(40-17(2)34)28(41-18(3)35)30(43-27(25)29(37)38-6)42-20-11-13-31(4)19(15-20)7-8-21-22-9-10-24(36)32(22,5)14-12-23(21)31/h19-23,25-28,30H,7-15H2,1-6H3/t19-,20+,21-,22-,23-,25-,26-,27-,28+,30+,31-,32-/m0/s1
• InChIKey: AMYSMHDMEUWMDZ-HFYWGREGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-yl]oxy}oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-yl]oxy}oxane-2-carboxylate
• Synonyms: 3α-(β-D-Glucopyranuronosyloxy)-5α-androstan-17-one Triacetate Methyl Ester; 17-Oxo-5α-androstan-3α-yl Glucopyranosiduronic Acid Triacetate Methyl Ester; Androsterone β-D-Glucuronide Triacetate Methyl Ester

Database IDs

• CAS Number: 21085-73-4
• PubChem SID: 162254776
• PubChem CID: 71313410

CALCULATED PROPERTIES

• Acid pKa: 19.96172
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 3.7859938
• LogD (pH = 7.4): 3.7859938
• Log P: 3.7859938
• Molar Refractivity: 148.3132 cm^3
• Polarizability: 60.71162 Å^3
• Polar Surface Area: 140.73 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: White Solid

Safety Information

• Storage Condition: Controlled Substance, Freezer

DETAILS

Toronto Research Chemicals - A637645

Protected Androsterone β-D-Glucuronide (A637605). (ADT-G) is one of the major circulating C19-steroid metabolites in humans. Exaggerated Androsterone (A637535) metabolism is observed in hyper-androgenic as well as in some normo-androgenic women with acne

REFERENCES

• Thompson, D.L. et al.: Clin. Endocrinol., 32, 283 (1990)
• Stener-Victorin, E. et al.: J. Clin. Endocrinol. Metab., 95, 810 (1990)