(2S,3S,4S,5R,6S)-6-{[(1S,2S,5R,7R,10R,11S,15S)-2,15-dimethyl-14-oxo(4,4,5,6,6-2H5)tetracyclo[8.7.0.02,7.011,15]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 160640
• Molecular Formular: C25H38O8
• Molecular Mass: 466.56442
• Monoisotopic Mass: 466.25666818
• 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]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: OC(=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]1O)O)O
• InChI: InChI=1S/C25H38O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-16,18-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,13-,14+,15+,16+,18+,19+,20-,21+,23-,24+,25+/m1/s1
• InChIKey: VFUIRAVTUVCQTF-SDHZCXLISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[(1S,2S,5R,7R,10R,11S,15S)-2,15-dimethyl-14-oxo(4,4,5,6,6-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[(1S,2S,5R,7R,10R,11S,15S)-2,15-dimethyl-14-oxo(4,4,5,6,6-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (3α,5β)-17-Oxoandrostan-3-yl-d5 β-D-Glucopyranosiduronic Αcid; 17-Oxo-5β-androstan-3α-yl-d5 β-D-Glucopyranosiduronic Acid; 3α-Hydroxy-5β-androstan-17-one-d5 Glucuronide; 5β-Androstan-3α-ol-17-one-d5 Glucuronide; Androstan-3-ol-17-one-d5 3-Glucuronide; Etiocholan-3α-ol-17-one-d5 3-Glucuronide; Etiocholan-3α-ol-17-one-d5 Glucuronide; Etiocholanolone-d5 Glucuronide; Etiocholanolone-d5 Glucuronoside; NSC 113100-d5; 5β-Androsterone-d5 β-D-Glucuronide

Database IDs

• PubChem SID: 162254775
• PubChem CID: 71313409

CALCULATED PROPERTIES

• Acid pKa: 3.4672441
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.2935807
• LogD (pH = 7.4): -1.0681946
• Log P: 2.3167233
• Molar Refractivity: 116.0896 cm^3
• Polarizability: 47.0811 Å^3
• Polar Surface Area: 133.52 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A637637

Labelled 5β-Androsterone β-D-Glucuronide (A637635). 5β-Androsterone β-D-Glucuronide is a glucuronide metabolite of Testosterone (T155000).

REFERENCES

• Weusten, J., et al.: J. Steroid Biochem., 32, 689 (1989)
• Antignac, J., et al.: Steroids, 70, 205 (1989)