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

• ChemBase ID: 155003
• Molecular Formular: C18H25NO4
• Molecular Mass: 319.3954
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

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

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 4.087685
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.98667955
• LogD (pH = 7.4): -0.6588317
• Log P: 2.1123233
• Molar Refractivity: 85.5618 cm^3
• Polarizability: 33.2816 Å^3
• Polar Surface Area: 83.47 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble20 mg/mL; H2O: soluble0.2 mg/mL; methanol: soluble20 mg/mL

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: >95% (HPLC)
• Biological Source: from Pseudomonas syringae pv Glycinea
• Empirical Formula (Hill Notation): C18H25NO4

DETAILS

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.