methyl (4S)-4-[(2'S,7'S,9'R,11'S,15'R,16'S)-9',16'-dihydroxy-2',15'-dimethylspiro[1,3-dioxolane-2,5'-tetracyclo[8.7.0.02,7.011,15]heptadecane]-14'-yl]pentanoate

• ChemBase ID: 173710
• Molecular Formular: C27H44O6
• Molecular Mass: 464.63466
• Monoisotopic Mass: 464.31378913
• SMILES: C1C2(C[C@H]3[C@](C1)(C1C([C@@H](C3)O)[C@H]3[C@]([C@H](C1)O)(C(CC3)[C@H](CCC(=O)OC)C)C)C)OCCO2
• Canonical SMILES: COC(=O)CC[C@@H](C1CC[C@@H]2[C@]1(C)[C@@H](O)CC1C2[C@H](O)C[C@@H]2[C@]1(C)CCC1(C2)OCCO1)C
• InChI: InChI=1S/C27H44O6/c1-16(5-8-23(30)31-4)18-6-7-19-24-20(14-22(29)26(18,19)3)25(2)9-10-27(32-11-12-33-27)15-17(25)13-21(24)28/h16-22,24,28-29H,5-15H2,1-4H3/t16-,17-,18?,19-,20?,21+,22-,24?,25-,26+/m0/s1
• InChIKey: CCYPUJZUSAYHRS-AFCIQXJVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (4S)-4-[(2'S,7'S,9'R,11'S,15'R,16'S)-9',16'-dihydroxy-2',15'-dimethylspiro[1,3-dioxolane-2,5'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane]-14'-yl]pentanoate
• IUPAC Traditional name: methyl (4S)-4-[(2'S,7'S,9'R,11'S,15'R,16'S)-9',16'-dihydroxy-2',15'-dimethylspiro[1,3-dioxolane-2,5'-tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecane]-14'-yl]pentanoate
• Synonyms: Methyl 3,3-Ethylenedioxy-7α,12α-dihydroxy-5α-cholanoate

Database IDs

• PubChem SID: 164229620
• PubChem CID: 71750349

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.0960293
• LogD (pH = 7.4): 3.0960295
• Log P: 3.0960295
• Molar Refractivity: 124.7799 cm^3
• Polarizability: 50.225395 Å^3
• Polar Surface Area: 85.22 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Methanol
• Apperance: Off-White Solid
• Melting Point: 172-175°C

DETAILS

Toronto Research Chemicals - M304880

Synthetic derivative of petromyzonol, a bile salt derivative isolated from the sea lamprey (Petromyzon marinus ) ammocoete (larval form). May be used to study the biochemical characteristics of these and other compounds containing the allocholic acid rin

REFERENCES

• Haslewood, G., et al.: Biochem. J., 114, 179 (1969)
• Sorensen, P.W., et al.: J. Gen. Physiol., 105, 569 (1995)