N-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide

• ChemBase ID: 153199
• Molecular Formular: C13H16N2O4
• Molecular Mass: 264.27714
• Monoisotopic Mass: 264.111007
• SMILES: CC(=O)NCCC(=O)c1cc(ccc1NC=O)OC
• Canonical SMILES: O=CNc1ccc(cc1C(=O)CCNC(=O)C)OC
• InChI: InChI=1S/C13H16N2O4/c1-9(17)14-6-5-13(18)11-7-10(19-2)3-4-12(11)15-8-16/h3-4,7-8H,5-6H2,1-2H3,(H,14,17)(H,15,16)
• InChIKey: JYWNYMJKURVPFH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide
• IUPAC Traditional name: N-[3-(2-formamido-5-methoxyphenyl)-3-oxopropyl]acetamide
• Synonyms: N-[3-[2-(Formylamino)-5-methoxyphenyl]-3-oxopropyl]acetamide; NSC 688263; AFMK; N1-Acetyl-N2-formyl-5-methoxykynuramine; N-γ-Acetyl-N-2-formyl-5-methoxykynurenamine

Database IDs

• CAS Number: 52450-38-1
• MDL Number: MFCD02683241
• PubChem SID: 24724387; 162247338
• PubChem CID: 171161

CALCULATED PROPERTIES

• Acid pKa: 13.901185
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.34396306
• LogD (pH = 7.4): 0.3439631
• Log P: 0.34396324
• Molar Refractivity: 70.7994 cm^3
• Polarizability: 26.407675 Å^3
• Polar Surface Area: 84.5 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble; Methanol
• Apperance: Light Brown Solid; white solid
• Melting Point: 138-140°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H319
• GHS Precautionary statements: P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C13H16N2O4

DETAILS

Sigma Aldrich - A2355

Biochem/physiol Actions
AFMK is a melatonin metabolite first detected in rat brain; demonstrates antioxidant and free radical scavenging activities in several experimental models; inhibits LPS-mediated production of TNFα and IL-8 in neutrophils; useful tool in the study of melatonin metabolism.

Toronto Research Chemicals - A176100

A metabolite of melatonin (M215000).

REFERENCES

• Mailliet, F., et al.: Biochem. Pharmacol., 71, 74 (2005)
• Leon, J., et al.: J. Neurochem., 98, 2023 (2005)
• Fagali, N., et al.: Life Sci., 81, 299 (2005)
• Ma, X., et al.: Endocrinol., 149, 1869 (2005)