sodium (4S)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentyl sulfate

• ChemBase ID: 176414
• Molecular Formular: C24H41NaO7S
• Molecular Mass: 496.63291
• Monoisotopic Mass: 496.24706893
• SMILES: C1[C@H](C[C@H]2[C@](C1)([C@@H]1[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)O.[Na+]
• Canonical SMILES: O[C@@H]1CC[C@]2([C@H](C1)C[C@H]([C@@H]1[C@@H]2C[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/C24H42O7S.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;/h14-22,25-27H,4-13H2,1-3H3,(H,28,29,30);/q;+1/p-1/t14-,15+,16+,17+,18-,19-,20+,21-,22-,23-,24+;/m0./s1
• InChIKey: DHGPBNKCHYMHIS-OPBQQCMKSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4S)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentyl sulfate
• IUPAC Traditional name: sodium (4S)-4-[(1S,2S,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentyl sulfate
• Synonyms: (3α,5α,7α,12α)-Cholane-3,7,12,24-tetrol 24-(Hydrogen Sulfate) Sodium; 5α-Cholane-3α,7α,12α,24-tetrol 24-(Hydrogen Sulfate) Sodium; 5α-Petromyzonol-24-sulfate Sodium; Petromyzonol Sulfate Sodium; PZS; Petromyzonol 24-Sulfate Sodium Salt

Database IDs

• CAS Number: 1271318-61-6
• PubChem SID: 164232324
• PubChem CID: 71751548

CALCULATED PROPERTIES

• Acid pKa: -1.7505809
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.04465594
• LogD (pH = 7.4): 0.044644725
• Log P: 0.8274879
• Molar Refractivity: 119.9227 cm^3
• Polarizability: 49.144604 Å^3
• Polar Surface Area: 127.12 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Off-White Solid
• Melting Point: >152°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - P293526

Petromyzonol sulfate (PZS) is a bile salt derivative isolated from the sea lamprey (Petromyzon marinus ) ammocoete (larval form). PZS appears to be a spawning chemoattractant for the sea lamprey.

REFERENCES

• Haslewood, G., et al.: Biochem. J., 114, 179 (1969)
• Sorensen, P.W., et al.: J. Gen. Physiol., 105, 569 (1969)