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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2019-07-16 16:49:12 UTC
Update Date2022-03-07 03:18:16 UTC
HMDB IDHMDB0240369
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Acetylaminophenoxazin-3-one
Description2-Acetylaminophenoxazin-3-one, also known as 2-acetamido-3-phenoxazone or N-acetylquestiomycin a, belongs to the class of organic compounds known as phenoxazines. These are polycyclic aromatic compounds containing a phenoxazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a 1,4-oxazine ring. Based on a literature review very few articles have been published on 2-Acetylaminophenoxazin-3-one.
Structure
Data?1563892757
Synonyms
ValueSource
N-(3-oxo-3H-Phenoxazin-2-yl)ethanimidateHMDB
2-(N-Acetylamino)-3-phenoxazoneHMDB
2-Acetamido-3-phenoxazoneHMDB
2-Acetaminophenoxazin-3-oneHMDB
2-Acetylamino-3H-phenoxazin-3-oneHMDB
N-(3-oxo-3H-Phenoxazin-2-yl)acetamideHMDB
N-Acetyl-2-amino-3H-phenoxazin-3-oneHMDB
N-Acetylquestiomycin aHMDB
2-Acetylaminophenoxazin-3-oneHMDB
Chemical FormulaC14H10N2O3
Average Molecular Weight254.245
Monoisotopic Molecular Weight254.06914219
IUPAC NameN-(3-oxo-3H-phenoxazin-2-yl)acetamide
Traditional NameN-(3-oxophenoxazin-2-yl)acetamide
CAS Registry Number1916-55-8
SMILES
CC(=O)NC1=CC2=NC3=CC=CC=C3OC2=CC1=O
InChI Identifier
InChI=1S/C14H10N2O3/c1-8(17)15-10-6-11-14(7-12(10)18)19-13-5-3-2-4-9(13)16-11/h2-7H,1H3,(H,15,17)
InChI KeyDWOBTNSFRDZSMA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenoxazines. These are polycyclic aromatic compounds containing a phenoxazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a 1,4-oxazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzoxazines
Sub ClassPhenoxazines
Direct ParentPhenoxazines
Alternative Parents
Substituents
  • Phenoxazine
  • N-acetylarylamine
  • N-arylamide
  • Benzenoid
  • Heteroaromatic compound
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Cyclic ketone
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.78ALOGPS
logP1.01ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)12.88ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area67.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity73.01 m³·mol⁻¹ChemAxon
Polarizability25.82 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+154.12530932474
DeepCCS[M-H]-151.76730932474
DeepCCS[M-2H]-184.7830932474
DeepCCS[M+Na]+160.21830932474
AllCCS[M+H]+156.132859911
AllCCS[M+H-H2O]+152.432859911
AllCCS[M+NH4]+159.632859911
AllCCS[M+Na]+160.632859911
AllCCS[M-H]-160.032859911
AllCCS[M+Na-2H]-159.432859911
AllCCS[M+HCOO]-158.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Acetylaminophenoxazin-3-oneCC(=O)NC1=CC2=NC3=CC=CC=C3OC2=CC1=O3383.1Standard polar33892256
2-Acetylaminophenoxazin-3-oneCC(=O)NC1=CC2=NC3=CC=CC=C3OC2=CC1=O2477.0Standard non polar33892256
2-Acetylaminophenoxazin-3-oneCC(=O)NC1=CC2=NC3=CC=CC=C3OC2=CC1=O2579.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Acetylaminophenoxazin-3-one,1TMS,isomer #1CC(=O)N(C1=CC2=NC3=CC=CC=C3OC2=CC1=O)[Si](C)(C)C2678.6Semi standard non polar33892256
2-Acetylaminophenoxazin-3-one,1TMS,isomer #1CC(=O)N(C1=CC2=NC3=CC=CC=C3OC2=CC1=O)[Si](C)(C)C2625.3Standard non polar33892256
2-Acetylaminophenoxazin-3-one,1TMS,isomer #1CC(=O)N(C1=CC2=NC3=CC=CC=C3OC2=CC1=O)[Si](C)(C)C3363.1Standard polar33892256
2-Acetylaminophenoxazin-3-one,1TBDMS,isomer #1CC(=O)N(C1=CC2=NC3=CC=CC=C3OC2=CC1=O)[Si](C)(C)C(C)(C)C2900.9Semi standard non polar33892256
2-Acetylaminophenoxazin-3-one,1TBDMS,isomer #1CC(=O)N(C1=CC2=NC3=CC=CC=C3OC2=CC1=O)[Si](C)(C)C(C)(C)C2822.3Standard non polar33892256
2-Acetylaminophenoxazin-3-one,1TBDMS,isomer #1CC(=O)N(C1=CC2=NC3=CC=CC=C3OC2=CC1=O)[Si](C)(C)C(C)(C)C3402.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Acetylaminophenoxazin-3-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylaminophenoxazin-3-one 10V, Positive-QTOFsplash10-08fr-0090000000-c13b512a2163871a57f72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylaminophenoxazin-3-one 20V, Positive-QTOFsplash10-03di-0090000000-577856e5ef81f7fd4ef62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylaminophenoxazin-3-one 40V, Positive-QTOFsplash10-08fr-0890000000-32f92429da0bd7a643c22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylaminophenoxazin-3-one 10V, Negative-QTOFsplash10-0w29-0090000000-636f8a65e9b27e4b82512021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylaminophenoxazin-3-one 20V, Negative-QTOFsplash10-03di-0090000000-110769cb8520d4f26a652021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylaminophenoxazin-3-one 40V, Negative-QTOFsplash10-01qi-0490000000-70068c4f5b09921da7f42021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID167772
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound193337
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Adhikari KB, Laerke HN, Mortensen AG, Fomsgaard IS: Plasma and urine concentrations of bioactive dietary benzoxazinoids and their glucuronidated conjugates in rats fed a rye bread-based diet. J Agric Food Chem. 2012 Nov 21;60(46):11518-24. doi: 10.1021/jf301737n. Epub 2012 Nov 12. [PubMed:23113707 ]
  2. Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]