(1R,3S)-5-{2-[(1R,3aS,7aR)-1-[(2R,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol hydrate

• ChemBase编号: 154550
• 分子式: C27H42O4
• 平均质量: 430.61998
• 单一同位素质量: 430.30830982
• SMILES: C[C@H](C=C[C@H](C1CC1)O)[C@H]1CC[C@@H]2[C@@]1(CCC/C/2=C\C=C\1/C[C@H](C[C@@H](C1=C)O)O)C.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](C=C[C@H](C2CC2)O)C)C)/C1.O
• InChI: InChI=1S/C27H40O3.H2O/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2;/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3;1H2/t17-,22-,23-,24+,25-,26+,27-;/m1./s1
• InChIKey: XBKHACNRWFKJNC-XYGBQYPUSA-N

名称和登记号

名称

• IUPAC标准名: (1R,3S)-5-{2-[(1R,3aS,7aR)-1-[(2R,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol hydrate
• IUPAC传统名: (1R,3S)-5-{2-[(1R,3aS,7aR)-1-[(2R,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-hexahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol hydrate
• 别名: (5Z,7E,22E,24S)-24-Cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1alpha,3beta,24-triol; Calcipotriene; Calcipotriol hydrate

登记号

• CAS号: 112965-21-6(anhydrous)
• MDL号: MFCD10567086
• PubChem SID: 162248688
• PubChem CID: 71311896

理论计算性质

• Acid pKa: 14.392874
• 质子受体: 3
• 质子供体: 3
• LogD (pH = 5.5): 3.8433506
• LogD (pH = 7.4): 3.8433506
• Log P: 3.843351
• 摩尔折射率: 125.4493 cm^3
• 极化性: 48.449245 Å^3
• 极化表面积: 60.69 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO: ≥24 mg/mL
• 外观: solid

安全信息

• RTECS编号: VS2830000
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H310-H315-H319-H335
• GHS警示性声明: P261-P280-P302 + P350-P305 + P351 + P338-P310
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• 保存温度: room temp

产品相关信息

• 纯度: ≥99% (HPLC)
• Empirical Formula (Hill Notation): C27H40O3 · xH2O

详细说明

Sigma Aldrich - C4369

Biochem/physiol Actions
Calcipotriol, a synthetic derivative of calcitriol or Vitamin D, is used in the treatment of psoriasis and marketed under the trade name Dovonex. It has comparable affinity with calcitriol (Vit. D) for the Vitamin D receptor (VDR), while being less than 1% as active as the calcitriol in regulating calcium metabolism. VDR belongs to the steroid/thyroid receptor superfamily, and is found on the cells of many different tissues including the thyroid, bone, kindney, and T cells of the immune system. Binding of calcipotriol to the VDR modulates the T cells gene transcription of cell differentiation and proliferation-related genes.