sodium (4S)-4-[(2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentyl sulfate

• ChemBase ID: 172089
• Molecular Formular: C24H39NaO7S
• Molecular Mass: 494.61703
• Monoisotopic Mass: 494.23141887
• SMILES: C1C(=O)C[C@H]2[C@](C1)(C1[C@@H]([C@@H](C2)O)[C@H]2[C@]([C@H](C1)O)([C@H](CC2)[C@H](CCCOS(=O)(=O)[O-])C)C)C.[Na+]
• Canonical SMILES: O=C1CC[C@]2([C@H](C1)C[C@H]([C@@H]1C2C[C@H](O)[C@]2([C@H]1CC[C@@H]2[C@H](CCCOS(=O)(=O)[O-])C)C)O)C.[Na+]
• InChI: InChI=1S/C24H40O7S.Na/c1-14(5-4-10-31-32(28,29)30)17-6-7-18-22-19(13-21(27)24(17,18)3)23(2)9-8-16(25)11-15(23)12-20(22)26;/h14-15,17-22,26-27H,4-13H2,1-3H3,(H,28,29,30);/q;+1/p-1/t14-,15+,17+,18-,19?,20+,21-,22-,23-,24+;/m0./s1
• InChIKey: OYFNOHKLEAJGRM-RDDDMFNBSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4S)-4-[(2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentyl sulfate
• IUPAC Traditional name: sodium (4S)-4-[(2S,7S,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentyl sulfate
• Synonyms: (5α,7α,12α)-7,12-Dihydroxy-5-cholan-3-one-24-sulfate Sodium Salt; (5α,7α,12α)-7,12-Dihydroxy-24-(sulfooxy)cholan-3-one Sodium; 3KPZS; 3-Keto Petromyzonol 24-Sulfate Sodium Salt

Database IDs

• PubChem SID: 164227999
• PubChem CID: 71749689

CALCULATED PROPERTIES

• Acid pKa: -1.5228758
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.25215703
• LogD (pH = 7.4): 0.25214553
• Log P: 1.101728
• Molar Refractivity: 118.8946 cm^3
• Polarizability: 48.603622 Å^3
• Polar Surface Area: 123.96 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 165-168°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - K200400

3-Keto Petromyzonol 24-Sulfate is a metabolite of Petromyzonol (P293500). 3-Keto Petromyzonol 24-Sulfate is also a mating pheromone released by male sea lampreys (Petromyzon marinus), at low picomolar concentration in natural waters to assess the presence

REFERENCES

• Bowers, L., et al.: Clin. Chem., 44, 375 (1998)
• Snyder, S., et al.: Environ. Sci. Technol., 33, 2814 (1998)
• Yun, et al.: Steroids, 68, 297 (2003)