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

• ChemBase编号: 72693
• 分子式: C27H44O3
• 平均质量: 416.63646
• 单一同位素质量: 416.32904527
• SMILES: [C@@H]1(C[C@@H](C(=C)/C(=C\C=C/2\[C@H]3[C@](CCC2)([C@H](CC3)[C@@H](CCCC(C)(C)O)C)C)/C1)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](CCCC(O)(C)C)C)C)/C1
• InChI: InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1
• InChIKey: GMRQFYUYWCNGIN-NKMMMXOESA-N

名称和登记号

名称

• IUPAC标准名: (1R,3S,5Z)-5-{2-[(1R,3aS,4E,7aR)-1-[(2R)-6-hydroxy-6-methylheptan-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
• IUPAC传统名: calcitriol
• 别名: (1R,3S,5Z)-4-Methylene-5-[(2E)-2-[(1R,3aS,7aS)-octahydro-1-[(1R)-5-hydroxy-1,5-dimethylhexyl]-7a-methyl-4H-inden-4-ylidene]ethylidene]-1,3-cyclohexanediol; (1α,3β,5Z,7E)- 9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol,; 1α,25-Dihydroxyvitamin D3; Dihydroxyvitamin D3; Panbonis; Ro 21-5535; Solbone P; Soltriol; Toptriol; 1α,25-Dihydroxycholecalciferol; Calcitriol; 1α,25-Dihydroxyvitamin D3; Calcijex; Silkis; Rocaltrol; Topitriol; Cholecalci; Calcitriol

登记号

• CAS号: 32222-06-3
• EC号: 250-963-8
• MDL号: MFCD00867079
• Beilstein号: 7559394
• PubChem SID: 162037614; 24893473
• PubChem CID: 5280453

理论计算性质

• Acid pKa: 14.392874
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): 4.350741
• LogD (pH = 7.4): 4.350741
• Log P: 4.350741
• 摩尔折射率: 126.5325 cm^3
• 极化性: 49.421616 Å^3
• 极化表面积: 60.69 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: Chloroform; DMSO; Do you have solubility information on this product that you would like to share?; Ethanol; Ethyl Acetate; Methanol; Tetrahydrofuran,
• 外观: White Solid
• 熔点: 119-121°C

安全信息

• 保存条件: -20°C; Amber Vial, -20°C Freezer
• RTECS编号: FZ4645000
• 欧盟危险性物质标志: 剧毒(Highly toxic) (T+)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 1
• 危险公开号: 63-26/27/28
• 安全公开号: 36/37/39-45
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H300-H310-H330-H361
• GHS警示性声明: P260-P264-P280-P284-P301 + P310-P302 + P350
• 个人保护装置: 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
• RID/ADR: UN 2811 6.1/PG 1
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... VDR(7421)

产品相关信息

• 纯度: ≥99% (HPLC)
• 成盐信息: Free Base
• 产品质量级别: PREMIUM

详细说明

Selleck Chemicals - S1466

Research Area: Metabolic Disease
Biological Activity:
Calcitriol, also called 1,25-dihydroxycholecalciferol or 1,25-dihydroxyvitamin D3, is the hormonally active form of vitamin D with three hydroxyl groups (abbreviated 1,25-(OH)2D3 or simply 1,25(OH)2D). It increases the level of calcium (Ca2+) in the blood by increasing the uptake of calcium from the gut into the blood, decreasing the transfer of calcium from blood to the urine by the kidney, and increasing the release of calcium into the blood from bone. [1]

Sigma Aldrich - D1530

Frequently Asked Questions
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Application
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Biochem/physiol Actions
Biologically active form of vitamin D3 in calcium absorption and deposition. 1α,25-Dihydroxyvitamin D3 has widespread effects on cellular differentiation and proliferation, and can modulate immune responsiveness, and central nervous system function. Recent studies suggest that 1α,25-dihydroxyvitamin D3 acts as a chemopreventive agent against several malignancies including cancers of the prostate and colon and shows synergy with other anticancer compounds.
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 in calcium absorption and deposition. 1α,25-Dihydroxyvitamin D3 has widespread effects on cellular differentiation and proliferation, and can modulate immune responsiveness, and central nervous system function. Recent studies suggest that 1α,25-dihydroxyvitamin D3 acts as a chemopreventive agent against several malignancies including cancers of the prostate and colon and shows synergy with other anticancer compounds.

Toronto Research Chemicals - C144500

The biologically active form of Vitamin D3. Calcium regulator; vitamin (antirachitic); antihyperparathyroid; antineoplastic; antipsoriatic.

参考文献

• http://en.wikipedia.org/wiki/Calcitriol
• Myrtle, J.F., et al.: J. Biol. Chem., 245, 1190 (1970)
• Lawson, D.E.M., et al.: Nature, 230, 228 (1970)
• Norman, A.W., et al.: Science, 173, 51 (1970)
• Suda, T., et al.: Vitamins, 45, 175 (1970)
• Muindi, J.R., et al.: Clin. Pharmacol. Ther., 72, 648 (2002