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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:00 UTC
HMDB IDHMDB0015503
Secondary Accession Numbers
  • HMDB15503
Metabolite Identification
Common NameAntipyrine
DescriptionAntipyrine, also known as phenazone or fenazona, belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group. In humans, antipyrine is involved in the antipyrine action pathway. Antipyrine 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 a significant number of articles have been published on Antipyrine.
Structure
Data?1582753304
Synonyms
ValueSource
1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-oneChEBI
2,3-Dimethyl-1-phenyl-5-pyrazoloneChEBI
FenazonaChEBI
PhenazoneChEBI
PhenazonumChEBI
AnalgesineHMDB
AnodyninHMDB
AnodynineHMDB
AntipirinHMDB
AntipyrinHMDB
AntipyrinumHMDB
AzophenHMDB
AzophenumHMDB
FenazoneHMDB
PhenozoneHMDB
PyramidoneHMDB
Chemical FormulaC11H12N2O
Average Molecular Weight188.2258
Monoisotopic Molecular Weight188.094963016
IUPAC Name1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
Traditional Nameantipyrine
CAS Registry Number60-80-0
SMILES
CN1N(C(=O)C=C1C)C1=CC=CC=C1
InChI Identifier
InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3
InChI KeyVEQOALNAAJBPNY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpyrazoles. Phenylpyrazoles are compounds containing a phenylpyrazole skeleton, which consists of a pyrazole bound to a phenyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassPyrazoles
Direct ParentPhenylpyrazoles
Alternative Parents
Substituents
  • Phenylpyrazole
  • Monocyclic benzene moiety
  • Pyrazolinone
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous amide
  • Lactam
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point114 °CNot Available
Boiling Point243.00 to 246.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility47.4 g/LNot Available
LogP0.38HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available137.849http://allccs.zhulab.cn/database/detail?ID=AllCCS00000943
Predicted Molecular Properties
PropertyValueSource
Water Solubility47.4 g/LALOGPS
logP1.18ALOGPS
logP1.22ChemAxon
logS-0.6ALOGPS
pKa (Strongest Basic)0.37ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area23.55 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity56.42 m³·mol⁻¹ChemAxon
Polarizability20.4 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+141.11331661259
DarkChem[M-H]-139.9631661259
DeepCCS[M+H]+138.61730932474
DeepCCS[M-H]-136.22130932474
DeepCCS[M-2H]-171.2130932474
DeepCCS[M+Na]+145.66930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AntipyrineCN1N(C(=O)C=C1C)C1=CC=CC=C12629.4Standard polar33892256
AntipyrineCN1N(C(=O)C=C1C)C1=CC=CC=C11763.6Standard non polar33892256
AntipyrineCN1N(C(=O)C=C1C)C1=CC=CC=C11770.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Antipyrine CI-B (Non-derivatized)splash10-000i-0900000000-1ac29db9e7ca9b1271ed2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Antipyrine EI-B (Non-derivatized)splash10-0550-9600000000-0c90aa2dd40a0fac3c482017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Antipyrine EI-B (Non-derivatized)splash10-000i-9600000000-297680e0a5f2e22c7de52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Antipyrine CI-B (Non-derivatized)splash10-000i-0900000000-1ac29db9e7ca9b1271ed2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Antipyrine EI-B (Non-derivatized)splash10-0550-9600000000-0c90aa2dd40a0fac3c482018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Antipyrine EI-B (Non-derivatized)splash10-000i-9600000000-297680e0a5f2e22c7de52018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Antipyrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ri-4900000000-83deafb6ee63b89d88302017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Antipyrine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Antipyrine 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 - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-001a-0900000000-94d2c7fe629bedc897b32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-ebc5f64904e52ff3d68e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-602baaec0430c9c48fc72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-a3fafbc8e8baf10dba962017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-ad19708445bbe9cd2bff2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-052s-2900000000-efb8c895ae384b102f762017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-0a4i-4900000000-80fc3f4f0ffbc6d8c8bb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-3a2d3f4534b07f6de8752017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-dbaaf801a6650b53331b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-0258999e6a4bf7041dea2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-4b511d8866a35ece5abd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-0a4s-2900000000-eea7fbb638b6e5146e902017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-0a4i-4900000000-80478740d36be900a6e72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-01q1-0900000000-e6dcb2d1a0ca860186fb2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-ae7f87ba95e0fc52493e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-1011-1900000000-a520cee151b2f2b6fcd12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-4fe0a2e33ea5e0c5c8762017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-ITFT , positive-QTOFsplash10-01wb-0900000000-1eaec6590298997b716e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Antipyrine LC-ESI-QTOF , positive-QTOFsplash10-000i-0900000000-65a45a9258dc65cd80a42017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antipyrine 10V, Positive-QTOFsplash10-000i-0900000000-75738b0061f94adaa1e72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antipyrine 20V, Positive-QTOFsplash10-000i-5900000000-11582ec37210a47ee3702016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antipyrine 40V, Positive-QTOFsplash10-0ki6-9100000000-ad117a2a6d3164d893e82016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antipyrine 10V, Negative-QTOFsplash10-000i-1900000000-442cd4768f9e324094e82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antipyrine 20V, Negative-QTOFsplash10-052r-2900000000-e823309262321fae485c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Antipyrine 40V, Negative-QTOFsplash10-0fr6-9200000000-10852cc4dc4bc0e299ac2016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01435 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01435 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01435
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2121
KEGG Compound IDC13244
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAntipyrine
METLIN IDNot Available
PubChem Compound2206
PDB IDNot Available
ChEBI ID31225
Food Biomarker OntologyNot Available
VMH IDANTIPYRENE
MarkerDB IDNot Available
Good Scents IDrw1498571
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available