[(1S,2R,5R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-yl]oxidanesulfonic acid

• ChemBase ID: 176910
• Molecular Formular: C21H34O6S
• Molecular Mass: 414.55606
• Monoisotopic Mass: 414.20760981
• SMILES: C1[C@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC[C@@]1([C@@H](O)C)O)C)OS(=O)(=O)O
• Canonical SMILES: C[C@@H]([C@@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@H](C2)OS(=O)(=O)O)O
• InChI: InChI=1S/C21H34O6S/c1-13(22)21(23)11-8-18-16-5-4-14-12-15(27-28(24,25)26)6-9-19(14,2)17(16)7-10-20(18,21)3/h4,13,15-18,22-23H,5-12H2,1-3H3,(H,24,25,26)/t13-,15+,16+,17-,18-,19-,20-,21-/m0/s1
• InChIKey: CKLXFJGOYPIIKV-KANDCNJNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1S,2R,5R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-yl]oxidanesulfonic acid
• IUPAC Traditional name: [(1S,2R,5R,10R,11S,14R,15S)-14-hydroxy-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-yl]oxidanesulfonic acid
• Synonyms: (3β,20S)-Pregn-5-ene-3,17,20-triol 3-(Hydrogen Sulfate); Pregn-5-ene-3β,17,20α-triol, 3-(Hydrogen Sulfate); (3β,20S)-Pregn-5-ene-3,17,20-triol Sulfate

Database IDs

• CAS Number: 4080-06-2
• PubChem SID: 164232820
• PubChem CID: 71751763

CALCULATED PROPERTIES

• Acid pKa: -1.3632758
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.12702014
• LogD (pH = 7.4): 0.12700582
• Log P: 1.1619259
• Molar Refractivity: 106.0737 cm^3
• Polarizability: 42.857502 Å^3
• Polar Surface Area: 104.06 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P712335

(3β,20R)-Pregn-5-ene-3,17,20-triol sulfate is a steroid metabolite of Pregnenolone sulfate.

REFERENCES

• Calvin, H.I., et al.: J. Clin. Endocrinol. Metab., 26, 402 (1966)