(3S,6R)-6-[(1R,3aS,7aR)-4-{2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol

• ChemBase ID: 153885
• Molecular Formular: C27H44O3
• Molecular Mass: 416.63646
• Monoisotopic Mass: 416.32904527
• SMILES: C[C@H](CC[C@@H](C(C)(C)O)O)[C@H]1CC[C@@H]2[C@@]1(CCC/C/2=C\C=C\1/C[C@H](CCC1=C)O)C
• Canonical SMILES: O[C@H]1CCC(=C)/C(=C/C=C/2\CCC[C@]3([C@H]2CC[C@@H]3[C@@H](CC[C@@H](C(O)(C)C)O)C)C)/C1
• InChI: InChI=1S/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/t19-,22+,23-,24+,25+,27-/m1/s1
• InChIKey: FCKJYANJHNLEEP-UWFSUSOLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6R)-6-[(1R,3aS,7aR)-4-{2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol
• IUPAC Traditional name: (3S,6R)-6-[(1R,3aS,7aR)-4-{2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-hexahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol
• Synonyms: (24S)-24,25-Dihydroxycholecalciferol; (24S)-24,25-Dihydroxyvitamin D3

Database IDs

• CAS Number: 55700-58-8
• MDL Number: MFCD11114064
• PubChem SID: 162248024
• PubChem CID: 71311749

CALCULATED PROPERTIES

• Acid pKa: 13.849643
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 4.5794425
• LogD (pH = 7.4): 4.5794425
• Log P: 4.5794425
• Molar Refractivity: 126.4221 cm^3
• Polarizability: 49.421616 Å^3
• Polar Surface Area: 60.69 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Highly toxic (T+)
• German water hazard class: 3
• Risk Statements: 28
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Product Information

• Purity: ≥99.0% (HPLC)
• Empirical Formula (Hill Notation): C27H44O3

DETAILS

Sigma Aldrich - 29447

Biochem/physiol Actions
Cholecalciferol is an inactive form of vitamin D3 which undergoes various levels of hydroxylation to form active vitamin D3 analogs. 1α-Hydroxyvitamin D3 (alfacalcidol) is a synthetic analog that is metabolized to 1,25-dihydroxycholecalciferol, the biologically active form of vitamin D3. Other analogues of cholecalciferol result from different hydroxylations. 24S,25-Dihydroxyvitamin D3 should not be confused with 24R,25-Dihydroxyvitamin D3.