sodium 2-[(4R)-4-[(1'S,2'S,5'R,7'R,11'S,14'R,15'R,16'S)-5',16'-dihydroxy-2',15'-dimethylspiro[diazirine-2,9'-tetracyclo[8.7.0.02,7.011,15]heptadecane]-14'-yl]pentanamido]ethane-1-sulfonate

• ChemBase ID: 161089
• Molecular Formular: C26H42N3NaO6S
• Molecular Mass: 547.68295
• Monoisotopic Mass: 547.26920136
• SMILES: C1[C@H](C[C@@H]2[C@](C1)([C@@H]1C(C3(C2)N=N3)[C@H]2[C@]([C@H](C1)O)([C@H](CC2)[C@@H](CCC(=O)NCCS(=O)(=O)[O-])C)C)C)O.[Na+]
• Canonical SMILES: O[C@@H]1CC[C@]2([C@@H](C1)CC1(C3[C@@H]2C[C@H](O)[C@]2([C@H]3CC[C@@H]2[C@@H](CCC(=O)NCCS(=O)(=O)[O-])C)C)N=N1)C.[Na+]
• InChI: InChI=1S/C26H43N3O6S.Na/c1-15(4-7-22(32)27-10-11-36(33,34)35)18-5-6-19-23-20(13-21(31)25(18,19)3)24(2)9-8-17(30)12-16(24)14-26(23)28-29-26;/h15-21,23,30-31H,4-14H2,1-3H3,(H,27,32)(H,33,34,35);/q;+1/p-1/t15-,16+,17-,18-,19+,20+,21+,23?,24+,25-;/m1./s1
• InChIKey: SBGNLQGGOAWPRY-UCXUEGNZSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 2-[(4R)-4-[(1'S,2'S,5'R,7'R,11'S,14'R,15'R,16'S)-5',16'-dihydroxy-2',15'-dimethylspiro[diazirine-2,9'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane]-14'-yl]pentanamido]ethane-1-sulfonate
• IUPAC Traditional name: sodium 2-[(4R)-4-[(1'S,2'S,5'R,7'R,11'S,14'R,15'R,16'S)-5',16'-dihydroxy-2',15'-dimethylspiro[diazirine-2,9'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane]-14'-yl]pentanamido]ethanesulfonate
• Synonyms: 2-[[(3α,5β,12α)-7-Azi-3,12-dihydroxy-24-oxocholan-24-yl]amino]ethanesulfonic Acid Sodium Salt; 7,7-Azo-3-α,12-α-dihydroxytaurocholanic Acid Sodium Salt

Database IDs

• CAS Number: 72741-86-7
• PubChem SID: 162255224
• PubChem CID: 46783655

CALCULATED PROPERTIES

• Acid pKa: -0.94327354
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -0.75697935
• LogD (pH = 7.4): -0.7570184
• Log P: 0.2846961
• Molar Refractivity: 132.9765 cm^3
• Polarizability: 53.716972 Å^3
• Polar Surface Area: 151.48 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: Pale Yellow Solid
• Melting Point: 170°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A945000

A photoaffinity probe for the hepatocyte bile acid transport system. Enquire about the radiolabelled compound.

REFERENCES

• J. Lipid Research, 24, 910 (1983)
• J. Biol. Chem., 258, 8890 (1983)