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

• ChemBase ID: 167902
• Molecular Formular: C28H44O3
• Molecular Mass: 428.64716
• Monoisotopic Mass: 428.32904527
• SMILES: C1[C@H](C[C@@H](C(=C)/C/1=C\C=C/1\[C@H]2[C@](CCC1)([C@H](CC2)[C@@H](/C=C/C(C(C)C)(O)C)C)C)O)O
• Canonical SMILES: O[C@H]1C[C@H](O)C(=C)/C(=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](/C=C/C(C(C)C)(O)C)C)C)/C1
• InChI: InChI=1S/C28H44O3/c1-18(2)28(6,31)15-13-19(3)24-11-12-25-21(8-7-14-27(24,25)5)9-10-22-16-23(29)17-26(30)20(22)4/h9-10,13,15,18-19,23-26,29-31H,4,7-8,11-12,14,16-17H2,1-3,5-6H3/b15-13+,21-9+,22-10-/t19-,23-,24-,25+,26+,27-,28?/m1/s1
• InChIKey: ODZFJAXAEXQSKL-GNMODTJUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E)-5-hydroxy-5-(^2H₃)methyl-6-methylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• IUPAC Traditional name: (1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E)-5-hydroxy-5-(^2H₃)methyl-6-methylhept-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• Synonyms: (1R,3S,4Z)-4-Methylene-5-[(2E)-2-[(1R,3aS,7aR)-octahydro-1-[(1R,2E)-4-hydroxy-1,4,5-trimethyl-2-hexen-1-yl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol-d3; 1,24-Dihydroxyvitamin D2-d3; 1α,24-Dihydroxyvitamin D2-d3; (1α,3β,5Z,7E,22E,24ξ)-9,10-Secoergosta-5,7,10(19),22-tetraene-1,3,24-triol-d3; 1α,24-Dihydroxy Vitamin D2-d3

Database IDs

• PubChem SID: 162262035
• PubChem CID: 71316282

CALCULATED PROPERTIES

• Acid pKa: 14.392874
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.587653
• LogD (pH = 7.4): 4.587653
• Log P: 4.587653
• Molar Refractivity: 131.8897 cm^3
• Polarizability: 51.0291 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D455107

Labelled analogue of 1α,24-Dihydroxyvitamin D2, a naturally occurring metabolite of vitamin D2 (V676040) with low calcemic activity and potent antiproliferative activity. 1α,24-Dihydroxyvitamin D2 is also a metabolite of 1α-Hydroxyvitamin D2 (H995800), a

REFERENCES

• Zinser, G.M. et al.: Anticancer Res., 25, 235 (2005)
• Mawer, E.B. et al.: J. Clin. Endocrinol. Metab., 83, 2156 (2005)
• Knutson, J.C. et al.: Biochem. Pharmacol., 53, 829 (2005)