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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-08-28 21:37:59 UTC
Update Date2021-09-26 22:48:54 UTC
HMDB IDHMDB0242266
Secondary Accession NumbersNone
Metabolite Identification
Common Name(+/-)-(e)-4-Ethyl-2-[(z)-hydroxyimino]-5-nitro-3-hexen-1-yl-nicotinamide
Description(+/-)-(e)-4-Ethyl-2-[(z)-hydroxyimino]-5-nitro-3-hexen-1-yl-nicotinamide belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group. Based on a literature review very few articles have been published on (+/-)-(e)-4-Ethyl-2-[(z)-hydroxyimino]-5-nitro-3-hexen-1-yl-nicotinamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). (+/-)-(e)-4-ethyl-2-[(z)-hydroxyimino]-5-nitro-3-hexen-1-yl-nicotinamide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (+/-)-(e)-4-Ethyl-2-[(z)-hydroxyimino]-5-nitro-3-hexen-1-yl-nicotinamide is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC14H18N4O4
Average Molecular Weight306.322
Monoisotopic Molecular Weight306.132805076
IUPAC NameN-[2-(ethoxyimino)-5-nitrohex-3-en-1-yl]pyridine-3-carboxamide
Traditional NameN-[2-(ethoxyimino)-5-nitrohex-3-en-1-yl]pyridine-3-carboxamide
CAS Registry NumberNot Available
SMILES
CCON=C(CNC(=O)C1=CN=CC=C1)C=CC(C)[N+]([O-])=O
InChI Identifier
InChI=1S/C14H18N4O4/c1-3-22-17-13(7-6-11(2)18(20)21)10-16-14(19)12-5-4-8-15-9-12/h4-9,11H,3,10H2,1-2H3,(H,16,19)
InChI KeyBSMGQVOYPQZEOC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nicotinamides. These are heterocyclic aromatic compounds containing a pyridine ring substituted at position 3 by a carboxamide group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentNicotinamides
Alternative Parents
Substituents
  • Nicotinamide
  • Heteroaromatic compound
  • Organic nitro compound
  • Secondary carboxylic acid amide
  • Oxime ether
  • C-nitro compound
  • Carboxamide group
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic zwitterion
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP1.77ALOGPS
logP1.21ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)9.19ChemAxon
pKa (Strongest Basic)3.68ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area106.72 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity80.4 m³·mol⁻¹ChemAxon
Polarizability31.2 ųChemAxon
Number of Rings1ChemAxon
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]+162.64330932474
DeepCCS[M-H]-159.89130932474
DeepCCS[M-2H]-194.78130932474
DeepCCS[M+Na]+170.9330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(+/-)-(e)-4-Ethyl-2-[(z)-hydroxyimino]-5-nitro-3-hexen-1-yl-nicotinamideCCON=C(CNC(=O)C1=CN=CC=C1)C=CC(C)[N+]([O-])=O3644.8Standard polar33892256
(+/-)-(e)-4-Ethyl-2-[(z)-hydroxyimino]-5-nitro-3-hexen-1-yl-nicotinamideCCON=C(CNC(=O)C1=CN=CC=C1)C=CC(C)[N+]([O-])=O2482.2Standard non polar33892256
(+/-)-(e)-4-Ethyl-2-[(z)-hydroxyimino]-5-nitro-3-hexen-1-yl-nicotinamideCCON=C(CNC(=O)C1=CN=CC=C1)C=CC(C)[N+]([O-])=O2608.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(+/-)-(e)-4-Ethyl-2-[(z)-hydroxyimino]-5-nitro-3-hexen-1-yl-nicotinamide,1TMS,isomer #1CCON=C(C=CC(C)[N+](=O)[O-])CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C2481.6Semi standard non polar33892256
(+/-)-(e)-4-Ethyl-2-[(z)-hydroxyimino]-5-nitro-3-hexen-1-yl-nicotinamide,1TMS,isomer #1CCON=C(C=CC(C)[N+](=O)[O-])CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C2144.3Standard non polar33892256
(+/-)-(e)-4-Ethyl-2-[(z)-hydroxyimino]-5-nitro-3-hexen-1-yl-nicotinamide,1TMS,isomer #1CCON=C(C=CC(C)[N+](=O)[O-])CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C3509.0Standard polar33892256
(+/-)-(e)-4-Ethyl-2-[(z)-hydroxyimino]-5-nitro-3-hexen-1-yl-nicotinamide,1TBDMS,isomer #1CCON=C(C=CC(C)[N+](=O)[O-])CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C2697.5Semi standard non polar33892256
(+/-)-(e)-4-Ethyl-2-[(z)-hydroxyimino]-5-nitro-3-hexen-1-yl-nicotinamide,1TBDMS,isomer #1CCON=C(C=CC(C)[N+](=O)[O-])CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C2324.6Standard non polar33892256
(+/-)-(e)-4-Ethyl-2-[(z)-hydroxyimino]-5-nitro-3-hexen-1-yl-nicotinamide,1TBDMS,isomer #1CCON=C(C=CC(C)[N+](=O)[O-])CN(C(=O)C1=CC=CN=C1)[Si](C)(C)C(C)(C)C3542.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (+/-)-(e)-4-Ethyl-2-[(z)-hydroxyimino]-5-nitro-3-hexen-1-yl-nicotinamide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-6890000000-c780814607f3c31b629b2021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+/-)-(e)-4-Ethyl-2-[(z)-hydroxyimino]-5-nitro-3-hexen-1-yl-nicotinamide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal 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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
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. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]