(3R,4aR,5S,6S,6aS,10S,10aR,10bS)-3-ethenyl-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-5-yl acetate

• ChemBase编号: 2315
• 分子式: C22H34O7
• 平均质量: 410.50116
• 单一同位素质量: 410.23045343
• SMILES: [C@H]1(O)CCC([C@@H]2[C@H](O)[C@H](OC(=O)C)[C@]3(O[C@](CC(=O)[C@]3(O)[C@@]12C)(C=C)C)C)(C)C
• Canonical SMILES: C=C[C@@]1(C)CC(=O)[C@]2([C@@](O1)(C)[C@@H](OC(=O)C)[C@H]([C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C)O)O
• InChI: InChI=1S/C22H34O7/c1-8-19(5)11-14(25)22(27)20(6)13(24)9-10-18(3,4)16(20)15(26)17(28-12(2)23)21(22,7)29-19/h8,13,15-17,24,26-27H,1,9-11H2,2-7H3/t13-,15-,16-,17-,19-,20-,21+,22-/m0/s1
• InChIKey: OHCQJHSOBUTRHG-KGGHGJDLSA-N

名称和登记号

名称

• IUPAC标准名: (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-3-ethenyl-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-dodecahydro-1H-naphtho[2,1-b]pyran-5-yl acetate
• IUPAC传统名: forskolin
• 别名: (3R,4aR,5S,6S,6aS,10S,10aR,10bS)-5-(Acetyloxy)-3-ethenyldodecahydro-6,10,10b-trihydroxy-3,4a,7,7,10a-pentamethyl-1H-Naphtho[2,1-b]pyran-1-one; (-)-Forskolin; ForsLean; HL 362; L 75-1362B; NSC 357088; 7β-Acetoxy-8,13-epoxy-1α,6β,9α-trihydroxylabd-14-en-11-one; Coleonol; Colforsin; Forskolin; Forskolin

登记号

• CAS号: 66428-89-5; 64657-11-0; 66575-29-9
• EC号: 266-410-9
• MDL号: MFCD00082317
• Beilstein号: 1692716
• PubChem SID: 160965767; 24894799; 46509044; 24278035
• PubChem CID: 47936
• CHEBI ID: 42471
• CHEMBL: 52606
• Chemspider ID: 43607
• DrugBank ID: DB02587
• 美国药典/FDA物质标识码: 1F7A44V6OU
• 维基百科标题: Forskolin

理论计算性质

JChem

• Acid pKa: 11.565541
• 质子受体: 6
• 质子供体: 3
• LogD (pH = 5.5): 1.3561152
• LogD (pH = 7.4): 1.356086
• Log P: 1.3561156
• 摩尔折射率: 104.4681 cm^3
• 极化性: 42.281574 Å^3
• 极化表面积: 113.29 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.28
• LOG S: -2.57
• 溶解度: 1.10e+00 g/l

分子性质

理化性质

• 溶解度: Chloroform; DMSO: soluble5 mg/mL (stable at least 6 months at room temperature); ethanol: soluble; Methanol; soluble in organic solvents such as ethanol, chloroform and DMSO
• 外观: off-white powder; White Solid
• 熔点: 219-222°C

安全信息

• 保存条件: -20°C Freezer
• RTECS编号: QL6150000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 21
• 安全公开号: 22-36/37
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H312
• GHS警示性声明: P280
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: -20°C

药理学性质

• 作用靶点: cAMP
• 相关基因信息: human ... OPRK1(4986), SLC2A10(81031), TNF(7124)

产品相关信息

• 纯度: ≥98%; ≥98% (HPLC); ≥98.0% (TLC)
• 级别: for molecular biology
• 成盐信息: Free Base
• 生物来源: from Coleus forskohlii
• 产品线: BioReagent
• Empirical Formula (Hill Notation): C22H34O7

详细说明

DrugBank - DB02587

• Drug Groups: experimental
• Description: Potent activator of the adenylate cyclase system and the biosynthesis of cyclic AMP. From the plant Coleus forskohlii. Has antihypertensive, positive ionotropic, platelet aggregation inhibitory, and smooth muscle relaxant activities; also lowers intraocular pressure and promotes release of hormones from the pituitary gland. [PubChem]
• External Links: Wikipedia; Drugs.com

Sigma Aldrich - F3917

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Analysis Note
Tested for inhibition of interleukin-2 production by Jurkat cells.
Biochem/physiol Actions
Cell-permeable diterpenoid that possesses anti-hypertensive, positive inotropic, and adenylyl cyclase activating properties. Many of its biological effects are due to its activation of adenylyl cyclase and the resulting increase in intracellular cAMP concentration.1 Forskolin effects calcium currents and inhibits MAP kinase.

Sigma Aldrich - F6886

Biochem/physiol Actions
Cell-permeable diterpenoid that possesses anti-hypertensive, positive inotropic, and adenylyl cyclase activating properties. Many of its biological effects are due to its activation of adenylyl cyclase and the resulting increase in intracellular cAMP concentration.1 Forskolin effects calcium currents and inhibits MAP kinase.

Sigma Aldrich - 47735

Biochem/physiol Actions
Cell-permeable diterpenoid that possesses anti-hypertensive, positive inotropic, and adenylyl cyclase activating properties. Many of its biological effects are due to its activation of adenylyl cyclase and the resulting increase in intracellular cAMP concentration.1 Forskolin effects calcium currents and inhibits MAP kinase.

Toronto Research Chemicals - F701800

Forskolin is a diterpene isolated from Coleus forskohlii, possessing vasodilating and cardiostimulatory properties. Forskolin resensitizes cell receptors by activating the enzyme adenylyl cyclase and increasing the intracellular levels of cAMP.

参考文献

• Lindner, E., et al.: Arzneim.-Forsch., 28, 284 (1984)
• Hoever, G., et al.: J. Med. Chem., 48, 1256 (1984)
• Lai, S., et al.: Eur. J. Clin. Microbiol. Infect. Dis., 24, 5831 (1984)