(1R,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-6-(2H3)methyl-5-methyl(7,7,7-2H3)hept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol

• ChemBase ID: 171451
• Molecular Formular: C28H44O2
• Molecular Mass: 412.64776
• Monoisotopic Mass: 412.33413065
• SMILES: C1[C@@H](CCC(=C)/C/1=C\C=C/1\[C@H]2[C@](CCC1)([C@H](CC2)[C@@H](/C=C/[C@@H](C(O)(C)C)C)C)C)O
• Canonical SMILES: O[C@@H]1CCC(=C)/C(=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](/C=C/[C@@H](C(O)(C)C)C)C)C)/C1
• InChI: InChI=1S/C28H44O2/c1-19-10-14-24(29)18-23(19)13-12-22-8-7-17-28(6)25(15-16-26(22)28)20(2)9-11-21(3)27(4,5)30/h9,11-13,20-21,24-26,29-30H,1,7-8,10,14-18H2,2-6H3/b11-9+,22-12+,23-13-/t20-,21+,24-,25-,26+,28-/m1/s1
• InChIKey: KJKIIUAXZGLUND-FOZBYKFWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-6-(^2H₃)methyl-5-methyl(7,7,7-^2H₃)hept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
• IUPAC Traditional name: (1R,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5S)-6-hydroxy-6-(^2H₃)methyl-5-methyl(7,7,7-^2H₃)hept-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
• Synonyms: (1R,3Z)-4-Methylene-3-[(2E)-2-[(1R,3aS,7aR)-octahydro-1-[(1R,2E,4S)-(5-hydroxy-1,4,5-trimethyl-2-hexen-1-yl)-d6]-7a-methyl-4H-inden-4-ylidene]ethylidene]cyclohexanol; (3α,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraene-3,25-diol-d6; 3-epi-25-Hydroxy Vitamin D2-d6

Database IDs

• PubChem SID: 164227361
• PubChem CID: 71749417

CALCULATED PROPERTIES

• Acid pKa: 18.384342
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 5.6573973
• LogD (pH = 7.4): 5.6573973
• Log P: 5.6573973
• Molar Refractivity: 130.6488 cm^3
• Polarizability: 50.44043 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H995842

A labelled epimer of 25-Hydroxy Vitamin D2 (H995820); a metabolite of Vitamin D2 (V676040) accounting for a significant proportion of total circulating 25-hydroxyvitamin D in infants.

REFERENCES

• Singh, R.J. et al.: J. Clin. Endocrinol. Metab., 91, 3055 (2006)
• Tai, S.S. et al.: Anal. Chem., 82, 1942 (2006)