N-(4-oxocyclohexa-2,5-dien-1-ylidene)acetamide

• ChemBase ID: 91335
• Molecular Formular: C8H7NO2
• Molecular Mass: 149.14668
• Monoisotopic Mass: 149.04767847
• SMILES: N(=C\1/C=CC(=O)C=C1)\C(=O)C
• Canonical SMILES: O=C1C=C/C(=N/C(=O)C)/C=C1
• InChI: InChI=1S/C8H7NO2/c1-6(10)9-7-2-4-8(11)5-3-7/h2-5H,1H3
• InChIKey: URNSECGXFRDEDC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(4-oxocyclohexa-2,5-dien-1-ylidene)acetamide
• IUPAC Traditional name: NABQ; N-acetyl-p-benzoquinone
• Synonyms: N-Acetyl-1,4-benzoquinone imine; N-(4-Oxocyclohexa-2,5-dien-1-ylidene)acetamide; N-(4-Oxo-1-cyclohexa-2,5-dienylidene)acetamide; NAPQI; N-Acetyl-p-benzo-quinoneimine; N-Acetylbenzoquinoneimine; 4-(Acetylimino)-2,5-cyclohexadien-1-one; Acetimidoquinone; N-Acetyl-p-benzoquinonimine; N-Acetyl-4-benzoquinone Imine; N-乙酰基对苯醌亚胺; N-乙酰苯醌亚胺

Database IDs

• CAS Number: 50700-49-7
• MDL Number: MFCD00078909
• PubChem SID: 24891199; 162078039
• PubChem CID: 39763

CALCULATED PROPERTIES

• Acid pKa: 19.13852
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.5732796
• LogD (pH = 7.4): 0.5732803
• Log P: 0.57328033
• Molar Refractivity: 42.4518 cm^3
• Polarizability: 15.1395445 Å^3
• Polar Surface Area: 46.5 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ether; Ethyl Acetate,
• Apperance: Pale Yellow Solid
• Melting Point: 74-75°C

Safety Information

• Storage Condition: Amber Vial, -86?C Freezer, Under Inert Atmosphere
• Storage Warning: Irritant/Store at -20°C
• RTECS: AC6960000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Empirical Formula (Hill Notation): C8H7NO2

DETAILS

Apollo Scientific Ltd - OR7000T

Toxic metabolite of acetaminophen, which reacts with serum proteins.

Sigma Aldrich - A7300

Other Notes
Acetaminophen metabolite that reacts with serum proteins.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A7300.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Packaging
1, 5 mg in serum btl
Application
Reactant involved in:
• Redox reactions1
• Hydrohalogenation2
• pH dependent reactions: in acidic media it is hydrolyzed, hydroxylated in alkaline media, and dimerized at intermediate pHs3
• Mediation of acetaminophen hepatotoxicity4
• Studies to identify the utility of acetaminophen for treating autoimmune disorders5

Toronto Research Chemicals - A170000

A toxic metabolite of Acetaminophen (A161220), which reacts with serum proteins.

REFERENCES

• Jaeschke, H., et al.: J. Pharmacol. Exp. Ther., 255, 935 (1990)
• Jaeschke, H., et al.: Toxicol. Lett., 144, 279 (1990)
• Jaeschke, H., et al.: Toxicol. Sci., 89, 31 (1990)
• Ray, S., et al.: Toxicol. Appl. Pharmacol., 106, 346 (1990)