(2R,4aS,6aS,12bR,14aS,14bR)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid

• ChemBase编号: 72612
• 分子式: C29H38O4
• 平均质量: 450.60962
• 单一同位素质量: 450.2770097
• SMILES: C1(=O)C(=C(C2=CC=C3[C@](C2=C1)(CC[C@@]1([C@@]3(CC[C@@]2([C@H]1C[C@](CC2)(C)C(=O)O)C)C)C)C)C)O
• Canonical SMILES: O=C1C=C2C(=CC=C3[C@@]2(C)CC[C@@]2([C@]3(C)CC[C@@]3([C@H]2C[C@@](C)(CC3)C(=O)O)C)C)C(=C1O)C
• InChI: InChI=1S/C29H38O4/c1-17-18-7-8-21-27(4,19(18)15-20(30)23(17)31)12-14-29(6)22-16-26(3,24(32)33)10-9-25(22,2)11-13-28(21,29)5/h7-8,15,22,31H,9-14,16H2,1-6H3,(H,32,33)/t22-,25-,26-,27+,28-,29+/m1/s1
• InChIKey: KQJSQWZMSAGSHN-JJWQIEBTSA-N

名称和登记号

名称

• IUPAC标准名: (2R,4aS,6aS,12bR,14aS,14bR)-10-hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydropicene-2-carboxylic acid
• IUPAC传统名: triterpene
• 别名: 3-Hydroxy-2-oxo-24-nor-D:A-friedooleana-1(10),3,5,7-tetraen-29-oic Acid; (9β,13α,14β,20α)-3-Hydroxy-9,13-dimethyl-2-oxo-24,25,26-trinoroleana-1(10),3,5,7-tetraen-29-oic Acid; Celastrol; 10-Hydroxy-2,4a,6a,9,12b,14a-hexamethyl-11-oxo-1,2,3,4,4a,5,6,6a,11,12b,13,14,14a,14b-tetradecahydro-picene-2-carboxylic acid; Tripterin; Celastrol

登记号

• CAS号: 34157-83-0
• MDL号: MFCD03424073
• PubChem SID: 162037537
• PubChem CID: 122724

理论计算性质

• Acid pKa: 4.7766385
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 4.5325603
• LogD (pH = 7.4): 2.754979
• Log P: 5.330474
• 摩尔折射率: 132.7461 cm^3
• 极化性: 50.732735 Å^3
• 极化表面积: 74.6 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO; DMSO: >10 mg/mL; H2O: insoluble; Methanol
• 外观: Orange Red Solid; red solid
• 熔点: 219-230°C

安全信息

• 保存条件: -20°C
• 欧盟危险性物质标志: 有毒(Toxic) (T)
• 联合国危险货物编号: 2811
• 德国WGK号: 2
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 25
• 安全公开号: 45
• GHS危险品标识: GHS06
• GHS警示词: Danger
• GHS危险声明: H301
• GHS警示性声明: P301 + P310
• 个人保护装置: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: -20°C

产品相关信息

• 纯度: ≥98% (HPLC)
• 成盐信息: Free Base
• Empirical Formula (Hill Notation): C29H38O4

详细说明

Selleck Chemicals - S1290

Research Area: Immunology
Biological Activity:
Celastrol, a plant-derived triterpene, has anti-inflammatory and immunosuppressive activity. It suppresses LPS-induced cytokine release in macrophages and monocytes (IC50=40nM for IL-1β and IL-1α, 80nM for IL-6, 110nM for prostaglandin E2 and 210nM for IL-8 and TNF-α). [1]

Sigma Aldrich - C0869

Biochem/physiol Actions
Celastrol is a potent antioxidant, and anti-inflammatory agent. It is a novel HSP90 inhibitor (disrupts Hsp90/Cdc37 complex), that exhibits anticancer (anti-angiogenic - suppresses VEGFR expression); antioxidant (inhibits lipid peroxidation) and anti-inflammatory activity (suppresses iNOS and inflammatory cytokine production).

Toronto Research Chemicals - C249500

An antioxidant natural product which inhibits the growth of human glioma xenografts in nude mice through suppressing VEGFR expression. Used for clinical treatment for rheumatoid arthritis, was demonstrated to have antiangiogenic activity, and be inhibito

参考文献

• Senger, D., et al.: Science, 219, 983 (1983)
• Folkman, J., et al.: Nature, 1, 27 (1983)
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• Grosios, K., et al.: Inflamm. Res., 53, 133 (1983)
• Yang, H., et al.: Cancer Res., 66, 4758 (1983)