[(1R,2R,6R,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(3-hydroxy-5-methoxyphenyl)acetate

• ChemBase编号: 133756
• 分子式: C37H40O9
• 平均质量: 628.7081
• 单一同位素质量: 628.26723286
• SMILES: C[C@@H]1C[C@]2([C@H]3C4[C@]1([C@@H]1C=C(C(=O)[C@]1(CC(=C4)COC(=O)Cc1cc(cc(c1)OC)O)O)C)O[C@](O3)(O2)Cc1ccccc1)C(=C)C
• Canonical SMILES: COc1cc(CC(=O)OCC2=CC3[C@H]4O[C@]5(O[C@]3([C@H]3[C@@](C2)(O)C(=O)C(=C3)C)[C@@H](C[C@@]4(O5)C(=C)C)C)Cc2ccccc2)cc(c1)O
• InChI: InChI=1S/C37H40O9/c1-21(2)35-17-23(4)37-29(33(35)44-36(45-35,46-37)19-24-9-7-6-8-10-24)14-26(18-34(41)30(37)11-22(3)32(34)40)20-43-31(39)15-25-12-27(38)16-28(13-25)42-5/h6-14,16,23,29-30,33,38,41H,1,15,17-20H2,2-5H3/t23-,29?,30-,33-,34-,35-,36-,37-/m1/s1
• InChIKey: IKYCZSUNGFRBJS-PMIKMUNESA-N

名称和登记号

名称

• IUPAC标准名: [(1R,2R,6R,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0^1,^1^0.0^2,^6.0^1^1,^1^5]octadeca-3,8-dien-8-yl]methyl 2-(3-hydroxy-5-methoxyphenyl)acetate
• IUPAC传统名: [(1R,2R,6R,11R,13S,15R,17R)-13-benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.0^1,^1^0.0^2,^6.0^1^1,^1^5]octadeca-3,8-dien-8-yl]methyl 2-(3-hydroxy-5-methoxyphenyl)acetate
• 别名: Resiniferatoxin aus Euphorbia poisonii; Resiniferatoxin

登记号

• CAS号: 57444-62-9
• MDL号: MFCD00135927
• Beilstein号: 5371150
• PubChem SID: 162228033; 24899411
• PubChem CID: 16219935

理论计算性质

• Acid pKa: 9.390471
• 质子受体: 8
• 质子供体: 2
• LogD (pH = 5.5): 5.588817
• LogD (pH = 7.4): 5.5844836
• Log P: 5.588873
• 摩尔折射率: 170.105 cm^3
• 极化性: 66.35148 Å^3
• 极化表面积: 120.75 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: false

分子性质

安全信息

• RTECS编号: CY1633700
• 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: 3
• 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: 25-35
• 安全公开号: 26-36/37/39-45
• GHS危险品标识: GHS05; GHS06
• GHS警示词: Danger
• GHS危险声明: H301-H314
• GHS警示性声明: P280-P305 + P351 + P338-P310
• 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 3
• 保存温度: -20°C

药理学性质

• 相关基因信息: rat ... Trpv1(83810)

产品相关信息

• 纯度: ~95%; ≥95% (HPLC)
• 生物来源: from Euphorbia poisonii
• Empirical Formula (Hill Notation): C37H40O9

详细说明

Sigma Aldrich - R8756

Biochem/physiol Actions
Potent VR1 vanilloid receptor agonist that has been used to label the vanilloid receptor in sensory ganglia; activates protein kinase C. Diterpene ester that is related to phorbol, but is not tumorigenic.

Sigma Aldrich - 83590

Other Notes
Phorbol-related diterpene ester of the daphnane type. Highly inflammatory, skin irritant (ID5/50 16 fmole/ear)1,2; Review (Pro-inflammatory, tumor-promoting and anti-tumor diterpenes of the plant families Euphorbiaceae and Thymeleaceae3