(1R,7S,10R,13R,14R)-7-[(3S,5R)-3,5-dihydroxy-2-methylcyclohex-1-en-1-yl]-14-methyl-13-[(2R)-6-methylheptan-2-yl]-4-phenyl-2,4,6-triazatetracyclo[7.7.0.02,6.010,14]hexadec-8-ene-3,5-dione

• ChemBase ID: 159644
• Molecular Formular: C35H49N3O4
• Molecular Mass: 575.78126
• Monoisotopic Mass: 575.37230706
• SMILES: C1[C@@H]2C(=C[C@@H](C3=C([C@H](C[C@@H](C3)O)O)C)n3n2c(=O)n(c3=O)c2ccccc2)[C@H]2[C@](C1)([C@H](CC2)[C@@H](CCCC(C)C)C)C
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@@H]1C2=C[C@H](n2n1c(=O)n(c2=O)c1ccccc1)C1=C(C)[C@H](C[C@@H](C1)O)O)C)C
• InChI: InChI=1S/C35H49N3O4/c1-21(2)10-9-11-22(3)28-14-15-29-27-20-31(26-18-25(39)19-32(40)23(26)4)38-34(42)36(24-12-7-6-8-13-24)33(41)37(38)30(27)16-17-35(28,29)5/h6-8,12-13,20-22,25,28-32,39-40H,9-11,14-19H2,1-5H3/t22-,25-,28-,29+,30-,31+,32+,35-/m1/s1
• InChIKey: PTIHYNIKYFVMFI-QLUNSSTRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,7S,10R,13R,14R)-7-[(3S,5R)-3,5-dihydroxy-2-methylcyclohex-1-en-1-yl]-14-methyl-13-[(2R)-6-methylheptan-2-yl]-4-phenyl-2,4,6-triazatetracyclo[7.7.0.0^2,^6.0^1^0,^1^4]hexadec-8-ene-3,5-dione
• IUPAC Traditional name: (1R,7S,10R,13R,14R)-7-[(3S,5R)-3,5-dihydroxy-2-methylcyclohex-1-en-1-yl]-14-methyl-13-[(2R)-6-methylheptan-2-yl]-4-phenyl-2,4,6-triazatetracyclo[7.7.0.0^2,^6.0^1^0,^1^4]hexadec-8-ene-3,5-dione
• Synonyms: pre-Alfacalcidol PTAD Adduct; [4aR-[4aα,6aα,7α(R*),9aβ,11α(3S*,5R*)]]-11-(3,5-dihydroxy-2-methyl-1-cyclohexen-1-yl)-7-(1,5-dimethylhexyl)-4a,6,6a,7,8,9,9a,11-octahydro-6a-methyl-2-phenyl-1H,5H-Cyclopenta[f][1,2,4]triazolo[1,2-a]cinnoline-1,3(2H)-dione

Database IDs

• PubChem SID: 162253779
• PubChem CID: 15102034

CALCULATED PROPERTIES

• Acid pKa: 14.417763
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 5.918338
• LogD (pH = 7.4): 5.918338
• Log P: 5.918338
• Molar Refractivity: 165.2596 cm^3
• Polarizability: 64.380424 Å^3
• Polar Surface Area: 84.32 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A524010

An Alfacalcidol (A524000) Impurity. A triazoline adduct of pre-alfacalcidol.

REFERENCES

• Holick, et al.: Science, 180, 190 (1973)
• Morisaki, M., et al.: Chem. Pharm. Bull., 23, 3272 (1973)