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

• ChemBase ID: 163545
• Molecular Formular: C35H49N3O5
• Molecular Mass: 591.78066
• Monoisotopic Mass: 591.36722168
• SMILES: C1[C@@H]2C(=C[C@H](n3n2c(=O)n(c3=O)c2ccccc2)C2=C([C@H](C[C@@H](C2)O)O)C)[C@H]2[C@](C1)([C@H](CC2)[C@@H](CCCC(O)(C)C)C)C
• Canonical SMILES: O[C@H]1C[C@H](O)C(=C(C1)[C@@H]1C=C2[C@H](n3n1c(=O)n(c3=O)c1ccccc1)CC[C@]1([C@H]2CC[C@@H]1[C@@H](CCCC(O)(C)C)C)C)C
• InChI: InChI=1S/C35H49N3O5/c1-21(10-9-16-34(3,4)43)27-13-14-28-26-20-30(25-18-24(39)19-31(40)22(25)2)38-33(42)36(23-11-7-6-8-12-23)32(41)37(38)29(26)15-17-35(27,28)5/h6-8,11-12,20-21,24,27-31,39-40,43H,9-10,13-19H2,1-5H3/t21-,24-,27-,28+,29-,30+,31+,35-/m1/s1
• InChIKey: AYDPRRXRNSGAGP-ZBKKTSFSSA-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]-13-[(2R)-6-hydroxy-6-methylheptan-2-yl]-14-methyl-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]-13-[(2R)-6-hydroxy-6-methylheptan-2-yl]-14-methyl-4-phenyl-2,4,6-triazatetracyclo[7.7.0.0^2,^6.0^1^0,^1^4]hexadec-8-ene-3,5-dione
• Synonyms: [4aR-[4aα,6aα,7α(R*),9aβ,11α(3S*,5R*)]]-11-(3,5-Dihydroxy-2-methyl-1-cyclohexen-1-yl)-4a,6,6a,7,8,9,9a,11-octahydro-7-(5-hydroxy-1,5-dimethylhexyl)-6a-methyl-2-phenyl-1H,5H-cyclopenta[f][1,2,4]triazolo[1,2-a]cinnoline-1,3(2H)-dione; pre-Calcitriol PTAD Adduct

Database IDs

• CAS Number: 86307-44-0
• PubChem SID: 162257680
• PubChem CID: 71314478

CALCULATED PROPERTIES

• Acid pKa: 14.417763
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 4.4472227
• LogD (pH = 7.4): 4.4472227
• Log P: 4.447223
• Molar Refractivity: 167.0957 cm^3
• Polarizability: 65.004944 Å^3
• Polar Surface Area: 104.55 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C144520

Calcitriol (C144500) impurity. 1α-Hydroxyvitamin D and 1α-hydroxyprevitamin D compounds were prepared in multistep syntheses via hydroxylation of previtamin D compound adducts with dienophiles.

REFERENCES

• Vanmaele, L., et al.: Tetrahedron, 41, 141 (1985)