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

• ChemBase ID: 941
• Molecular Formular: C28H46O
• Molecular Mass: 398.66424
• Monoisotopic Mass: 398.35486609
• SMILES: OC1C/C(=C/C=C\2/C3C(C(CC3)C(C)/C=C/C(C(C)C)C)(CCC2)C)/C(CC1)C
• Canonical SMILES: OC1CCC(/C(=C\C=C\2/CCCC3(C2CCC3C(/C=C/C(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-
• InChIKey: ILYCWAKSDCYMBB-AAGLSAJLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3Z)-3-{2-[(4E)-1-[(3E)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylcyclohexan-1-ol; 3-{2-[1-(5,6-dimethylhept-3-en-2-yl)-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylcyclohexan-1-ol
• IUPAC Traditional name: dihydrotachysterol; 3-{2-[1-(5,6-dimethylhept-3-en-2-yl)-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylcyclohexan-1-ol
• Brand Name: Antitanil; Calcamine; DHT Intensol; Dichystrolum; Dihydral; Dygratyl; Hytakerol; Parterol; Tachystin
• Synonyms: Vitamin D4; Dihydrotachysterol; Dihydrotachysterol; DIHYDROTACHYSTEROL, CRYST

Database IDs

• CAS Number: 67-96-9
• PubChem SID: 160964404
• PubChem CID: 5281010

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 7.86
• LOG S: -6.5
• Solubility (Water): 1.25e-04 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 7.5

DETAILS

MP Biomedicals - 05213006

MP Biomedicals Rare Chemical collection

DrugBank - DB01070

• Drug Groups: approved
• Description: A vitamin D that can be regarded as a reduction product of vitamin D2. [PubChem]
• Indication: Used for the prevention and treatment of rickets or osteomalacia, and to manage hypocalcemia associated with hypoparathyroidism or pseudohypoparathyroidism. Also used for the treatment of vitamin D dependent rickets, rickets or osteomalacia secondary to long-term high dose anticonvulsant therapy, early renal osteodystrophy, osteoporosis (in conjunction with calcium), and hypophosphatemia associated with Fanconi syndrome (with treatment of acidosis).
• Pharmacology: Dihydrotachysterol is hydroxylated in the liver to 25-hydroxydihydrotachysterol, which is the major circulating active form of the drug. It does not undergo further hydroxylation by the kidney and therefore is the analogue of 1, 25-dihydroxyvitamin D. Dihydrotachysterol is effective in the elevation of serum calcium by stimulating intestinal calcium absorption and mobilizing bone calcium in the absence of parathyroid hormone and of functioning renal tissue. Dihydrotachysterol also increases renal phosphate excretion.
• Toxicity: Toxicity associated with dihydrotachysterol is similar to that seen with large doses of vitamin D.
• Affected Organisms: Humans and other mammals
• Protein Binding: >99%
• References: DeLuca HF: Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr. 2004 Dec;80(6 Suppl):1689S-96S. [Pubmed] ; Bosch R, Thijssen JH, Duursma SA: Action and metabolism of dihydrotachysterol2. J Steroid Biochem. 1987;27(4-6):829-36. [Pubmed] ; Pierides AM: Pharmacology and therapeutic use of vitamin D and its analogues. Drugs. 1981 Apr;21(4):241-56. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• DeLuca HF: Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr. 2004 Dec;80(6 Suppl):1689S-96S. Pubmed
• Bosch R, Thijssen JH, Duursma SA: Action and metabolism of dihydrotachysterol2. J Steroid Biochem. 1987;27(4-6):829-36. Pubmed
• Pierides AM: Pharmacology and therapeutic use of vitamin D and its analogues. Drugs. 1981 Apr;21(4):241-56. Pubmed