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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 23:32:55 UTC
Update Date2021-10-01 18:51:03 UTC
HMDB IDHMDB0246531
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Nitrobenzaldehyde
Description4-nitrobenzaldehyde belongs to the class of organic compounds known as nitrobenzaldehydes. These are nitrobenzenes that carry an aldehyde group at any position of the benzene ring. Based on a literature review a small amount of articles have been published on 4-nitrobenzaldehyde. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-nitrobenzaldehyde is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Nitrobenzaldehyde 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
Synonyms
ValueSource
p-NitrobenzaldehydeChEBI
4-Nitrobenzaldehyde, ion(1-), potassium saltMeSH
4-Nitrobenzaldehyde, ion(1-)MeSH
Para-nitrobenzaldehydeMeSH
4-Nitrobenzaldehyde, 1-(13)C-labeledMeSH
4-Nitrobenzaldehyde, aldehyde-(18)O-labeledMeSH
Chemical FormulaC7H5NO3
Average Molecular Weight151.1195
Monoisotopic Molecular Weight151.026943031
IUPAC Name4-nitrobenzaldehyde
Traditional Name4-nitrobenzaldehyde
CAS Registry NumberNot Available
SMILES
O=CC1=CC=C(C=C1)N(=O)=O
InChI Identifier
InChI=1S/C7H5NO3/c9-5-6-1-3-7(4-2-6)8(10)11/h1-5H
InChI KeyBXRFQSNOROATLV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitrobenzaldehydes. These are nitrobenzenes that carry an aldehyde group at any position of the benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNitrobenzenes
Direct ParentNitrobenzaldehydes
Alternative Parents
Substituents
  • Nitrobenzaldehyde
  • Benzaldehyde
  • Nitroaromatic compound
  • Benzoyl
  • Aryl-aldehyde
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Aldehyde
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
logP1.45ALOGPS
logP1.63ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area62.89 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.97 m³·mol⁻¹ChemAxon
Polarizability13.43 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+129.11530932474
DeepCCS[M-H]-125.28430932474
DeepCCS[M-2H]-162.60230932474
DeepCCS[M+Na]+138.14230932474
AllCCS[M+H]+130.332859911
AllCCS[M+H-H2O]+125.832859911
AllCCS[M+NH4]+134.632859911
AllCCS[M+Na]+135.832859911
AllCCS[M-H]-125.832859911
AllCCS[M+Na-2H]-126.932859911
AllCCS[M+HCOO]-128.232859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 202213.2586 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.36 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1474.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid478.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid155.6 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid307.3 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid103.4 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid434.8 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid617.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)317.2 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1075.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid385.3 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1141.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid382.6 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid444.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate601.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA512.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water181.2 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-NitrobenzaldehydeO=CC1=CC=C(C=C1)N(=O)=O2486.7Standard polar33892256
4-NitrobenzaldehydeO=CC1=CC=C(C=C1)N(=O)=O1316.5Standard non polar33892256
4-NitrobenzaldehydeO=CC1=CC=C(C=C1)N(=O)=O1362.3Semi standard non polar33892256
Spectra
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 ID526
KEGG Compound IDNot Available
BioCyc IDCPD-703
BiGG IDNot Available
Wikipedia Link4-Nitrobenzaldehyde
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID66926
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 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Accessory potassium channel protein which modulates the activity of the pore-forming alpha subunit. Alters functional properties of Kv1.4
Gene Name:
KCNAB2
Uniprot ID:
Q13303
Molecular weight:
40999.9
General function:
Not Available
Specific function:
Cytoplasmic potassium channel subunit that modulates the characteristics of the channel-forming alpha-subunits (PubMed:9763623, PubMed:21357749). Contributes to the regulation of nerve signaling, and prevents neuronal hyperexcitability (By similarity). Promotes expression of the pore-forming alpha subunits at the cell membrane, and thereby increases channel activity (PubMed:10896669, PubMed:16770729, PubMed:18003609, PubMed:21357749). Promotes potassium channel closure via a mechanism that does not involve physical obstruction of the channel pore (PubMed:21357749). Modulates the functional properties of KCNA4 (PubMed:9763623). Modulates the functional properties of KCNA5 (By similarity). Enhances KCNB2 channel activity (By similarity). Binds NADPH and has NADPH-dependent aldoketoreductase activity (PubMed:18672894, PubMed:21209188). Has broad substrate specificity and can catalyze the reduction of methylglyoxal, 9,10-phenanthrenequinone, prostaglandin J2, 4-nitrobenzaldehyde, 4-nitroacetophenone and 4-oxo-trans-2-nonenal (in vitro) (PubMed:18672894).
Gene Name:
KCNAB2
Uniprot ID:
P62483
Molecular weight:
41020.95