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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:37:04 UTC
Update Date2021-10-13 06:08:24 UTC
HMDB IDHMDB0030483
Secondary Accession Numbers
  • HMDB30483
Metabolite Identification
Common NameQuestiomycin A
DescriptionQuestiomycin A, also known as isophenoxazine or 2-aminophenoxazon, 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. Questiomycin A is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Questiomycin A.
Structure
Data?1563861992
Synonyms
ValueSource
IsophenoxazineChEBI
3-AminophenoxazoneKegg
2-Amino-3-phenoxazoneHMDB
2-Amino-3H-phenoxazin-3-oneHMDB
2-Amino-phenoxazin-3-oneHMDB
2-Aminophenoxazin-3-oneHMDB
2-AminophenoxazonHMDB
2-AminophenoxazoneHMDB
Acrospermum viticola toxin CHMDB
AV toxin CHMDB
NSC 94945HMDB
PHX-3 CPDHMDB
2-Acetylamino-(3H)-phenoxazin-3-oneHMDB
2-Aminophenoxazine-3-oneHMDB
Questinomycine aHMDB
Questiomycin aChEBI
Questiomycin AHMDB
Chemical FormulaC12H8N2O2
Average Molecular Weight212.2041
Monoisotopic Molecular Weight212.05857751
IUPAC Name2-amino-3H-phenoxazin-3-one
Traditional Name2-aminophenoxazin-3-one
CAS Registry Number1916-59-2
SMILES
NC1=CC2=NC3=CC=CC=C3OC2=CC1=O
InChI Identifier
InChI=1S/C12H8N2O2/c13-7-5-9-12(6-10(7)15)16-11-4-2-1-3-8(11)14-9/h1-6H,13H2
InChI KeyRDJXPXHQENRCNG-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
  • Benzenoid
  • Heteroaromatic compound
  • Cyclic ketone
  • Azacycle
  • Oxacycle
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility40350 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP10(1.06) g/LALOGPS
logP10(1.19) g/LChemAxon
logS10(-3) g/LALOGPS
pKa (Strongest Acidic)19.95ChemAxon
pKa (Strongest Basic)-0.29ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.68 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity63.57 m³·mol⁻¹ChemAxon
Polarizability21.36 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
DarkChem[M+H]+148.22931661259
DarkChem[M-H]-146.48831661259
DeepCCS[M+H]+144.84630932474
DeepCCS[M-H]-142.31130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Questiomycin ANC1=CC2=NC3=CC=CC=C3OC2=CC1=O3028.4Standard polar33892256
Questiomycin ANC1=CC2=NC3=CC=CC=C3OC2=CC1=O2274.6Standard non polar33892256
Questiomycin ANC1=CC2=NC3=CC=CC=C3OC2=CC1=O2419.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Questiomycin A,1TMS,isomer #1C[Si](C)(C)NC1=CC2=NC3=CC=CC=C3OC2=CC1=O2578.8Semi standard non polar33892256
Questiomycin A,1TMS,isomer #1C[Si](C)(C)NC1=CC2=NC3=CC=CC=C3OC2=CC1=O2480.5Standard non polar33892256
Questiomycin A,2TMS,isomer #1C[Si](C)(C)N(C1=CC2=NC3=CC=CC=C3OC2=CC1=O)[Si](C)(C)C2606.1Semi standard non polar33892256
Questiomycin A,2TMS,isomer #1C[Si](C)(C)N(C1=CC2=NC3=CC=CC=C3OC2=CC1=O)[Si](C)(C)C2577.9Standard non polar33892256
Questiomycin A,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC2=NC3=CC=CC=C3OC2=CC1=O2854.7Semi standard non polar33892256
Questiomycin A,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC1=CC2=NC3=CC=CC=C3OC2=CC1=O2672.2Standard non polar33892256
Questiomycin A,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC2=NC3=CC=CC=C3OC2=CC1=O)[Si](C)(C)C(C)(C)C2995.9Semi standard non polar33892256
Questiomycin A,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(C1=CC2=NC3=CC=CC=C3OC2=CC1=O)[Si](C)(C)C(C)(C)C2953.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Questiomycin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-3950000000-170e4f3cf8ec253fbb132017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Questiomycin A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Questiomycin A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Questiomycin A LC-ESI-qTof , Positive-QTOFsplash10-000i-0910000000-f6e8b189198fb21b8fbf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Questiomycin A , positive-QTOFsplash10-000i-0910000000-f6e8b189198fb21b8fbf2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Questiomycin A 10V, Positive-QTOFsplash10-03di-0090000000-c592ec79c93eefd902e12015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Questiomycin A 20V, Positive-QTOFsplash10-03di-0190000000-f02aff344c005054cf3c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Questiomycin A 40V, Positive-QTOFsplash10-0w90-8930000000-22e0d3ec0ba2457a6eef2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Questiomycin A 10V, Negative-QTOFsplash10-03di-0090000000-0f3befc55c4faa386e5b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Questiomycin A 20V, Negative-QTOFsplash10-03di-0090000000-88fa56ded28a83b408722015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Questiomycin A 40V, Negative-QTOFsplash10-0r09-3910000000-68edb98bc915f41d997f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Questiomycin A 10V, Negative-QTOFsplash10-03di-0090000000-fb1be335f42676557e202021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Questiomycin A 20V, Negative-QTOFsplash10-03di-0090000000-fb1be335f42676557e202021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Questiomycin A 40V, Negative-QTOFsplash10-03e9-0590000000-1ba841e0e4c2e8f3ebf52021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Questiomycin A 10V, Positive-QTOFsplash10-03di-0090000000-056698109127ac4a7b162021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Questiomycin A 20V, Positive-QTOFsplash10-03di-0090000000-056698109127ac4a7b162021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Questiomycin A 40V, Positive-QTOFsplash10-0a4i-0920000000-b6773186f686365fde822021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB002352
KNApSAcK IDC00018683
Chemspider ID65565
KEGG Compound IDC02161
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkQuestiomycin A
METLIN IDNot Available
PubChem Compound72725
PDB IDNot Available
ChEBI ID17293
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1820341
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  3. 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 ]