(1S)-3-[(Z)-2-[(1R,3aR,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethenyl]-4-methylcyclohex-3-en-1-ol

• ChemBase ID: 176917
• Molecular Formular: C27H44O
• Molecular Mass: 384.63766
• Monoisotopic Mass: 384.33921603
• SMILES: C1(=CCC[C@]2([C@H]1CC[C@@H]2[C@@H](CCCC(C)C)C)C)/C=C\C1=C(CC[C@@H](C1)O)C
• Canonical SMILES: CC(CCC[C@H]([C@H]1CC[C@@H]2[C@]1(C)CCC=C2/C=C\C1=C(C)CC[C@@H](C1)O)C)C
• InChI: InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h10,12-13,19,21,24-26,28H,6-9,11,14-18H2,1-5H3/b13-12-/t21-,24+,25-,26+,27-/m1/s1
• InChIKey: YUGCAAVRZWBXEQ-WHTXLNIXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-3-[(Z)-2-[(1R,3aR,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]ethenyl]-4-methylcyclohex-3-en-1-ol
• IUPAC Traditional name: previtamin D3
• Synonyms: Precalciferol3; Precholecalciferol; Previtamin D; Precalciferol; (3β,6Z)-9,10-Secocholesta-5(10),6,8-trien-3-ol; 9,10-Secocholesta-5(10),6,8-trien-3β-ol; (1S)-3-[(1Z)-2-[(1R,3aR,7aR)-1-[(1R)-1,5-Dimethylhexyl]-2,3,3a,6,7,7a-hexahydro-7a-methyl-1H-inden-4-yl]ethenyl]-4-methyl-3-Cyclohexen-1-ol; Previtamin D3

Database IDs

• CAS Number: 1173-13-3
• PubChem SID: 164232827
• PubChem CID: 5281058

CALCULATED PROPERTIES

• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false
• Acid pKa: 18.314426
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 7.067527
• LogD (pH = 7.4): 7.0675273
• Log P: 7.0675273
• Molar Refractivity: 124.297 cm^3
• Polarizability: 48.251457 Å^3

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Oil

DETAILS

Toronto Research Chemicals - P713510

Vitamin D3 (V676045) isomer. Vitamin D3 mediates intestinal calcium absorbtion, bone calcium metabolism and many other processes. During exposure to sunlight 7-dehydrocholesterol in converted to pre-vitamin D3, which undergoes a rapid transformation withi

REFERENCES

• Holick, M. et al.; J. Bone. Miner. Metab. 22, V28 (2007)
• Tian, X. & Holick, M.; J. Biol. Chem. 270, 8706 (1995)