Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:46 UTC
HMDB IDHMDB0014871
Secondary Accession Numbers
  • HMDB14871
Metabolite Identification
Common NamePralidoxime
DescriptionPralidoxime is an antidote to organophosphate pesticides and chemicals. Organophosphates bind to the esteratic site of acetylcholinesterase, which results initially in reversible inactivation of the enzyme. If given within 24 hours,after organophosphate exposure, pralidoxime reactivates the enzyme cholinesterase by cleaving the phosphate-ester bond formed between the organophosphate and acetylcholinesterase.
Structure
Data?1582753230
Synonyms
ValueSource
PralidoximumChEBI
Pralidoxime chlorideHMDB
Chemical FormulaC7H9N2O
Average Molecular Weight137.1592
Monoisotopic Molecular Weight137.07148792
IUPAC Name2-[(1E)-(hydroxyimino)methyl]-1-methylpyridin-1-ium
Traditional Namepralidoximum
CAS Registry Number6735-59-7
SMILES
C[N+]1=C(\C=N\O)C=CC=C1
InChI Identifier
InChI=1S/C7H8N2O/c1-9-5-3-2-4-7(9)6-8-10/h2-6H,1H3/p+1
InChI KeyJBKPUQTUERUYQE-UHFFFAOYSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-methylpyridinium compounds. These are methylpyridines that carry a methyl group at the 1-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassMethylpyridines
Direct ParentN-methylpyridinium compounds
Alternative Parents
Substituents
  • N-methylpyridinium
  • Pyridinium
  • Heteroaromatic compound
  • Aldoxime
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point215 - 225 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.15 g/LNot Available
LogP1.564Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP-3ALOGPS
logP-3.3ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)5.78ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area36.47 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity40.33 m³·mol⁻¹ChemAxon
Polarizability14.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+127.79530932474
DeepCCS[M-H]-125.15230932474
DeepCCS[M-2H]-161.14430932474
DeepCCS[M+Na]+136.15630932474
AllCCS[M+H]+126.932859911
AllCCS[M+H-H2O]+122.232859911
AllCCS[M+NH4]+131.332859911
AllCCS[M+Na]+132.632859911
AllCCS[M-H]-129.932859911
AllCCS[M+Na-2H]-131.632859911
AllCCS[M+HCOO]-133.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PralidoximeC[N+]1=C(\C=N\O)C=CC=C11698.7Standard polar33892256
PralidoximeC[N+]1=C(\C=N\O)C=CC=C11345.7Standard non polar33892256
PralidoximeC[N+]1=C(\C=N\O)C=CC=C11402.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pralidoxime GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-3900000000-fed95af6893d175a5ee52017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pralidoxime GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pralidoxime 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 - Pralidoxime LC-ESI-QQ , positive-QTOFsplash10-000i-0900000000-20fdfd5334ead907481e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pralidoxime LC-ESI-QQ , positive-QTOFsplash10-00kr-1900000000-28213070bfa027f763962017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pralidoxime LC-ESI-QQ , positive-QTOFsplash10-00kf-9600000000-e526d65f27b45380a4012017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pralidoxime LC-ESI-QQ , positive-QTOFsplash10-0006-9100000000-5b6d1f4a0b4b4f3b44d82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pralidoxime LC-ESI-QQ , positive-QTOFsplash10-014l-9000000000-dcac00013d3eaf2dd6d92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pralidoxime LC-ESI-QTOF , positive-QTOFsplash10-00ko-4900000000-030938e55f082376a8fc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Pralidoxime LC-ESI-QTOF , positive-QTOFsplash10-00kf-9200000000-7ee2419716b3f943ce852017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pralidoxime 10V, Positive-QTOFsplash10-000i-0900000000-1fe13bf7e67cc57b36ec2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pralidoxime 20V, Positive-QTOFsplash10-000i-1900000000-261bb67d8a3b585f3d812016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pralidoxime 40V, Positive-QTOFsplash10-0a4i-9400000000-28e10229dfe4c0908bd02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pralidoxime 10V, Negative-QTOFsplash10-000i-0900000000-07f797a1ec1bdb7b8c8e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pralidoxime 20V, Negative-QTOFsplash10-000i-3900000000-476a09d3ca8cc71f5ff02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pralidoxime 40V, Negative-QTOFsplash10-0a4l-9000000000-db4d06eaed81884e2d562016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00733 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00733 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00733
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5193737
KEGG Compound IDC07400
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPralidoxime
METLIN IDNot Available
PubChem Compound6789253
PDB IDNot Available
ChEBI ID8354
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 ReferencesNot Available

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular weight:
67795.525
References
  1. Jokanovic M, Prostran M: Pyridinium oximes as cholinesterase reactivators. Structure-activity relationship and efficacy in the treatment of poisoning with organophosphorus compounds. Curr Med Chem. 2009;16(17):2177-88. [PubMed:19519385 ]
  2. Kovacic P: Mechanism of organophosphates (nerve gases and pesticides) and antidotes: electron transfer and oxidative stress. Curr Med Chem. 2003 Dec;10(24):2705-9. [PubMed:14529460 ]
  3. Jokanovic M: Medical treatment of acute poisoning with organophosphorus and carbamate pesticides. Toxicol Lett. 2009 Oct 28;190(2):107-15. doi: 10.1016/j.toxlet.2009.07.025. Epub 2009 Aug 3. [PubMed:19651196 ]
  4. Wong L, Radic Z, Bruggemann RJ, Hosea N, Berman HA, Taylor P: Mechanism of oxime reactivation of acetylcholinesterase analyzed by chirality and mutagenesis. Biochemistry. 2000 May 16;39(19):5750-7. [PubMed:10801325 ]
General function:
Involved in carboxylesterase activity
Specific function:
Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:
BCHE
Uniprot ID:
P06276
Molecular weight:
68417.575
References
  1. Pohanka M, Jun D, Kuca K: In vitro reactivation of trichlorfon-inhibited butyrylcholinesterase using HI-6, obidoxime, pralidoxime and K048. J Enzyme Inhib Med Chem. 2009 Jun;24(3):680-3. doi: 10.1080/14756360802328315. [PubMed:18825528 ]
  2. Khan S, Hemalatha R, Jeyaseelan L, Oommen A, Zachariah A: Neuroparalysis and oxime efficacy in organophosphate poisoning: a study of butyrylcholinesterase. Hum Exp Toxicol. 2001 Apr;20(4):169-74. [PubMed:11393267 ]