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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 12:16:24 UTC
Update Date2021-09-26 23:06:52 UTC
HMDB IDHMDB0253570
Secondary Accession NumbersNone
Metabolite Identification
Common NameIproniazid
DescriptionIproniazid belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. Pyridinecarboxylic acids and derivatives are compounds containing a pyridine ring bearing a carboxylic acid group or a derivative thereof. Iproniazid is a drug which is used for the treatment of depression (originally intended to treat tuberculosis). Iproniazid is a strong basic compound (based on its pKa). Hepatic necrosis was found in rats with doses as low as 10 mg/kg. This compound has been identified in human blood as reported by (PMID: 31557052 ). Iproniazid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Iproniazid 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
IproniazideChEMBL
IprazidMeSH
Chemical FormulaC9H13N3O
Average Molecular Weight179.219
Monoisotopic Molecular Weight179.105862053
IUPAC NameN'-(propan-2-yl)pyridine-4-carbohydrazide
Traditional Nameiproniazid
CAS Registry NumberNot Available
SMILES
CC(C)NNC(=O)C1=CC=NC=C1
InChI Identifier
InChI=1S/C9H13N3O/c1-7(2)11-12-9(13)8-3-5-10-6-4-8/h3-7,11H,1-2H3,(H,12,13)
InChI KeyNYMGNSNKLVNMIA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. Pyridinecarboxylic acids and derivatives are compounds containing a pyridine ring bearing a carboxylic acid group or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridinecarboxylic acids and derivatives
Direct ParentPyridinecarboxylic acids and derivatives
Alternative Parents
Substituents
  • Pyridine carboxylic acid or derivatives
  • Heteroaromatic compound
  • Carboxylic acid hydrazide
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP0.02ALOGPS
logP0.31ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)13.66ChemAxon
pKa (Strongest Basic)3.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.02 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60.96 m³·mol⁻¹ChemAxon
Polarizability19.19 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]+139.25330932474
DeepCCS[M-H]-136.37530932474
DeepCCS[M-2H]-172.92930932474
DeepCCS[M+Na]+148.46730932474
AllCCS[M+H]+140.632859911
AllCCS[M+H-H2O]+136.432859911
AllCCS[M+NH4]+144.532859911
AllCCS[M+Na]+145.632859911
AllCCS[M-H]-141.532859911
AllCCS[M+Na-2H]-142.532859911
AllCCS[M+HCOO]-143.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IproniazidCC(C)NNC(=O)C1=CC=NC=C12263.2Standard polar33892256
IproniazidCC(C)NNC(=O)C1=CC=NC=C11589.9Standard non polar33892256
IproniazidCC(C)NNC(=O)C1=CC=NC=C11628.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Iproniazid,1TMS,isomer #1CC(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C1692.5Semi standard non polar33892256
Iproniazid,1TMS,isomer #1CC(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C1773.2Standard non polar33892256
Iproniazid,1TMS,isomer #1CC(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C2214.2Standard polar33892256
Iproniazid,1TMS,isomer #2CC(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C1635.7Semi standard non polar33892256
Iproniazid,1TMS,isomer #2CC(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C1714.0Standard non polar33892256
Iproniazid,1TMS,isomer #2CC(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C2118.2Standard polar33892256
Iproniazid,2TMS,isomer #1CC(C)N(N(C(=O)C1=CC=NC=C1)[Si](C)(C)C)[Si](C)(C)C1685.8Semi standard non polar33892256
Iproniazid,2TMS,isomer #1CC(C)N(N(C(=O)C1=CC=NC=C1)[Si](C)(C)C)[Si](C)(C)C1793.2Standard non polar33892256
Iproniazid,2TMS,isomer #1CC(C)N(N(C(=O)C1=CC=NC=C1)[Si](C)(C)C)[Si](C)(C)C2032.1Standard polar33892256
Iproniazid,1TBDMS,isomer #1CC(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C1937.7Semi standard non polar33892256
Iproniazid,1TBDMS,isomer #1CC(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C1947.1Standard non polar33892256
Iproniazid,1TBDMS,isomer #1CC(C)N(NC(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C2328.5Standard polar33892256
Iproniazid,1TBDMS,isomer #2CC(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C1851.0Semi standard non polar33892256
Iproniazid,1TBDMS,isomer #2CC(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C1925.1Standard non polar33892256
Iproniazid,1TBDMS,isomer #2CC(C)NN(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C2241.5Standard polar33892256
Iproniazid,2TBDMS,isomer #1CC(C)N(N(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2161.9Semi standard non polar33892256
Iproniazid,2TBDMS,isomer #1CC(C)N(N(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2193.5Standard non polar33892256
Iproniazid,2TBDMS,isomer #1CC(C)N(N(C(=O)C1=CC=NC=C1)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2276.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Iproniazid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-8900000000-d786226d5db93593d8de2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Iproniazid 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 - Iproniazid 10V, Positive-QTOFsplash10-001r-0900000000-49e950c0a9fa3a055b3c2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iproniazid 20V, Positive-QTOFsplash10-000i-1900000000-8affb6a605c559ecb93d2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iproniazid 40V, Positive-QTOFsplash10-0a4u-9500000000-ef4944e3da7f09e3f3332017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iproniazid 10V, Negative-QTOFsplash10-004i-1900000000-70c20dd8c669b103896b2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iproniazid 20V, Negative-QTOFsplash10-004i-4900000000-f332cce024a43397b9d52017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iproniazid 40V, Negative-QTOFsplash10-0006-9100000000-380364d4d62d96f3f0c62017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iproniazid 10V, Positive-QTOFsplash10-001i-0900000000-eeed42b0f7d83a85dffb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iproniazid 20V, Positive-QTOFsplash10-0a4i-0900000000-9a58baefb65b09e234e42021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iproniazid 40V, Positive-QTOFsplash10-003r-9200000000-cce8a523785f5ede4bce2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iproniazid 10V, Negative-QTOFsplash10-004i-0900000000-139fe46b0bf366caedda2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iproniazid 20V, Negative-QTOFsplash10-002f-9100000000-bd9f875c29ef9d0121dc2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Iproniazid 40V, Negative-QTOFsplash10-002f-9000000000-990dd797d2e961cdcaad2021-10-12Wishart 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 IDDB04818
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC11777
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIproniazid
METLIN IDNot Available
PubChem Compound3748
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 ]