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

• ChemBase ID: 167714
• Molecular Formular: C28H46O
• Molecular Mass: 398.66424
• Monoisotopic Mass: 398.35486609
• SMILES: C1C/C(=C\C=C/2\[C@H](CC[C@@H](C2)O)C)/[C@H]2[C@](C1)([C@H](CC2)[C@@H](/C=C/[C@@H](C(C)C)C)C)C
• Canonical SMILES: O[C@H]1CC[C@@H](/C(=C/C=C/2\CCC[C@]3([C@H]2CC[C@@H]3[C@@H](/C=C/[C@@H](C(C)C)C)C)C)/C1)C
• InChI: InChI=1S/C28H46O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-22,25-27,29H,7-8,11,14-18H2,1-6H3/b10-9+,23-12+,24-13+/t20-,21-,22+,25-,26+,27-,28+/m0/s1
• InChIKey: ILYCWAKSDCYMBB-OPCMSESCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3E,4S)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylcyclohexan-1-ol
• IUPAC Traditional name: dihydrotachysterol
• Synonyms: (3β,5E,7E,10α,22E)-9,10-Secoergosta-5,7,22-trien-3-ol; 24-Methyl-9,10-secocholesta-5,7,22-trien-3β-ol; Antitanil; Calcamine; DHT2; Dichystrolum; Dihydral; Tachyrol; Dihydro Tachysterol; (1S,3E,4S)-4-Methyl-3-[(2E)-2-[(1R,3aS,7aR)-octahydro-7a-methyl-1-[(1R,2E,4R)-1,4,5-trimethyl-2-hexen-1-yl]-4H-onden-4-ylidene]ethylidene]cyclohexanol

Database IDs

• CAS Number: 67-96-9
• PubChem SID: 162261847
• PubChem CID: 5311071

CALCULATED PROPERTIES

• Acid pKa: 18.296175
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 7.398204
• LogD (pH = 7.4): 7.398204
• Log P: 7.398204
• Molar Refractivity: 129.1122 cm^3
• Polarizability: 50.09825 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 116-120°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer

DETAILS

Toronto Research Chemicals - D449550

Calcium regulator. Preparation by reduction of Tachysterol. It is widely used for hypocalcemic hypoparathyroidism following surgical removal of parathyroids.

REFERENCES

• Schilling, T., et al.: Exp. Clin. Endocrinol. Diabetes, 105, 237 (1997)
• Bushinsky, D., et al.: Lancet, 352, 306 (1997)
• Jehle, D., et al.: J. Med., 30, 39 (1997)
• Winer, K., et al.: J. Clin. Endocrinol. Metab., 88, 4214 (1997)