2-ethyl-1-(6-ethyl-1-oxo-2,3,3a,6,7,7a-hexahydro-1H-indene-4-amido)cyclopropane-1-carboxylic acid

• ChemBase编号: 155003
• 分子式: C18H25NO4
• 平均质量: 319.3954
• 单一同位素质量: 319.17835829
• SMILES: CCC1CC2C(CCC2=O)C(=C1)C(=O)NC1(CC1CC)C(=O)O
• Canonical SMILES: CCC1C=C(C(=O)NC2(CC2CC)C(=O)O)C2C(C1)C(=O)CC2
• InChI: InChI=1S/C18H25NO4/c1-3-10-7-13-12(5-6-15(13)20)14(8-10)16(21)19-18(17(22)23)9-11(18)4-2/h8,10-13H,3-7,9H2,1-2H3,(H,19,21)(H,22,23)
• InChIKey: FMGBNISRFNDECK-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-ethyl-1-(6-ethyl-1-oxo-2,3,3a,6,7,7a-hexahydro-1H-indene-4-amido)cyclopropane-1-carboxylic acid
• IUPAC传统名: 2-ethyl-1-(6-ethyl-1-oxo-2,3,3a,6,7,7a-hexahydroindene-4-amido)cyclopropane-1-carboxylic acid
• 别名: COR; Cyclopropanecarboxylic acid,2-ethyl-1-[[(6-ethyl-2,3,3a,6,7a-hexahydro-1-oxo-1H-inden-4-yl)carbonyl] amino]; Coronatine

登记号

• MDL号: MFCD06798335
• PubChem SID: 162249141
• PubChem CID: 11347733

理论计算性质

• Acid pKa: 4.087685
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 0.98667955
• LogD (pH = 7.4): -0.6588317
• Log P: 2.1123233
• 摩尔折射率: 85.5618 cm^3
• 极化性: 33.2816 Å^3
• 极化表面积: 83.47 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: soluble20 mg/mL; H2O: soluble0.2 mg/mL; methanol: soluble20 mg/mL

安全信息

• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

产品相关信息

• 纯度: >95% (HPLC)
• 生物来源: from Pseudomonas syringae pv Glycinea
• Empirical Formula (Hill Notation): C18H25NO4

详细说明

Sigma Aldrich - C8115

Application
Coronatine is a polyketide phytotoxin produced by several members of the Pseudomonas syringae group of pathovars such as atropurpurea, glycinea, maculicola,morsprunorum and tomato. Coronatine is used to study three regulatory genes: corP, corS and corR1. It is used to study the stimulation of ethylene synthesis in Nicotiana tabacum leaves2.
Biochem/physiol Actions
Coronatine consists of two distinct structural components that function as biosynthetic intermediates: coronafacic acid (CFA) and coronamic acid (CMA)1. It is known to induce hypertrophy and chlorosis, inhibit root elongation, and stimulate ethylene production1.