methyl (4R)-4-[(1S,2S,5R,7R,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl(4,4,5,6,6-2H5)tetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]pentanoate

• ChemBase ID: 179409
• Molecular Formular: C25H42O4
• Molecular Mass: 406.59858
• Monoisotopic Mass: 406.30830982
• SMILES: C1C[C@H](C[C@@H]2[C@]1([C@@H]1[C@@H]([C@H](C2)O)[C@H]2[C@](CC1)([C@H](CC2)[C@@H](CCC(=O)OC)C)C)C)O
• Canonical SMILES: COC(=O)CC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2[C@@H](O)C[C@H]2[C@]1(C)CC[C@H](C2)O)C
• InChI: InChI=1S/C25H42O4/c1-15(5-8-22(28)29-4)18-6-7-19-23-20(10-12-25(18,19)3)24(2)11-9-17(26)13-16(24)14-21(23)27/h15-21,23,26-27H,5-14H2,1-4H3/t15-,16+,17-,18-,19+,20+,21+,23+,24+,25-/m1/s1
• InChIKey: GRQROVWZGGDYSW-ZQMFMVRBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (4R)-4-[(1S,2S,5R,7R,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl(4,4,5,6,6-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoate
• IUPAC Traditional name: methyl (4R)-4-[(1S,2S,5R,7R,9S,10R,11S,14R,15R)-5,9-dihydroxy-2,15-dimethyl(4,4,5,6,6-^2H₅)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]pentanoate
• Synonyms: (3α,5β,7β)-3,7-Dihydroxycholan-24-oic-2,2,3,4,4-d5 Acid Methyl Ester; 3α,7β-Dihydroxy-5β-cholanic Acid-d5 Methyl Ester; Methyl 3α,7β-Dihydroxy-5β-cholanoate-d5; Methyl Ursodeoxycholate-d5; Ursodeoxycholic Acid-d5 Methyl Ester

Database IDs

• CAS Number: 93701-19-0
• PubChem SID: 164235319
• PubChem CID: 45040672

CALCULATED PROPERTIES

• Acid pKa: 18.296339
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 3.8591993
• LogD (pH = 7.4): 3.8591995
• Log P: 3.8591995
• Molar Refractivity: 114.0429 cm^3
• Polarizability: 45.86178 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 59-62°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - U850052

A precursor to manufacture UDCA (Ursodeoxycholic acid) which is useful for cholesterol gallstone dissolution and fish growth promoter.

REFERENCES

• Parks, D., et al.: Science, 284, 1365 (1999)
• Kawamata, Y., et al.: J. Biol. Chem., 278, 9435 (1999)
• Pellicciari, R., et al.: J. Med. Chem., 48, 5383 (1999)
• Acconcia, F., et al.: Cancer Lett., 238, 1 (1999)