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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-22 18:56:27 UTC

Update Date

2023-02-21 17:17:16 UTC

HMDB ID

HMDB0006240

Secondary Accession Numbers

HMDB06240

Metabolite Identification

Common Name

Demethylated antipyrine

Description

Demethylated antipyrine is a novel potent free radical scavenger that has been clinically used to reduce the neuronal damage following ischemic stroke. Demethylated antipyrine exerts neuroprotective effects by inhibiting endothelial injury and by ameliorating neuronal damage in brain ischemia. Demethylated antipyrine provides the desirable features of NOS: it increases eNOS (beneficial NOS for rescuing ischemic stroke) and decreases nNOS and iNOS (detrimental NOS). Post- reperfusion brain edema and hemorrhagic events induced by thrombolytic therapy may be reduced by demethylated antipyrine pretreatment. Increased productions of superoxide and NO in the brain after reperfusion and a concomitant surge in oxygen free radicals with increased NO during recirculation lead to formation of peroxynitrite, a super potent radical. Demethylated antipyrine, which inhibits oxidation and enhances NO production derived from increased eNOS expression, may improve and conserve cerebral blood flow without peroxynitrite generation during reperfusion. Clinical experience with demethylated antipyrine suggests that this drug has a wide therapeutic time window. Demethylated antipyrine can exert a wide range of inhibitory effects on water-soluble and lipid soluble peroxyl radical-induced peroxidation systems, and appears to display combined properties of both, vitamin C and E. Demethylated antipyrine can scavenge not only hydroxyl radicals but also other free radicals, although it has no major effect on superoxide anion radicals. Demethylated antipyrine apparently traps hydroxyl radicals and inhibits OH-dependent lipid peroxidation or tyrosine nitration induced by peroxynitrite (ONOO-). Lipid peroxidation starts with lipid radical (L) production after free radical-mediated extraction of proton from unsaturated fatty acid. Subsequently lipid peroxyl radical (LOO) is generated by addition of oxygen atom, and a further L is produced by LOO-mediated extraction of proton from another unsaturated fatty acid. Demethylated antipyrine can inhibit lipid peroxidation by scavenging not only hydroxyl radicals but also other free radicals including LOO. Under physiological conditions, 50% of demethylated antipyrine is present as an anion form, and electrons released from demethylated antipyrine anion exert radical scavenging. Subsequently, demethylated antipyrine radicals are generated. They react readily with oxygen atoms, and form peroxyl radical of demethylated antipyrine, and eventually 2-oxo-3-(phenylhydrazone)- butanoic acid (OPB). (PMID: 16834755 , CNS Drug Rev. 2006 Spring;12(1):9-20.).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      29.739 -21.588   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      31.072 -22.358   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.072 -23.898   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.739 -24.668   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.405 -23.898   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.405 -22.358   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      29.739 -20.048   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      28.493 -19.143   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      30.985 -19.143   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      30.509 -17.678   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.969 -17.678   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      28.063 -16.432   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      32.449 -19.619   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8    9                                                  
CONECT    8    7   11                                                       
CONECT    9    7   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10    8   12                                                  
CONECT   12   11                                                            
CONECT   13    9                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Phenyl-3-methyl-1H-4,5-dihydropyrazol-5-one	HMDB
1-Phenyl-3-methyl-2-pyrazolin-5-one	HMDB
1-Phenyl-3-methyl-5-oxopyrazole	HMDB
1-Phenyl-3-methyl-5-pyrazolinone	HMDB
1-Phenyl-3-methyl-5-pyrazolone	HMDB
2,4-dihydro-5-Methyl-2-phenyl-3H-pyrazol-3-one	HMDB
3-Methyl-1-phenyl-1H-pyrazol-5-one	HMDB
3-Methyl-1-phenyl-2-pyrazolin-5-one	HMDB
3-Methyl-1-phenyl-2-pyrazoline-5-one	HMDB
3-Methyl-1-phenyl-4,5-dihydropyrazol-5-one	HMDB
3-Methyl-1-phenyl-4,5-dihydropyrazole-5-one	HMDB
3-Methyl-1-phenyl-5-pyrazolone	HMDB
3-Methyl-1-phenylpyrazol-5(4H)-one	HMDB
3-Methyl-1-phenylpyrazolin-5-one	HMDB
5-Methyl-2-phenyl-2H-pyrazol-3(4H)-one	HMDB
5-Methyl-2-phenylpyrazol-3-one	HMDB
Edarabone	HMDB
Edaravone	HMDB
Methylphenylpyrazolone	HMDB
Norantipyrine	HMDB
Norphenazone	HMDB
N-Demethylantipyrine, 14C-labeled	MeSH, HMDB
N-Demethylantipyrine	MeSH, HMDB

Chemical Formula

C₁₀H₁₀N₂O

Average Molecular Weight

174.1992

Monoisotopic Molecular Weight

174.079312952

IUPAC Name

5-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one

Traditional Name

5-methyl-2-phenyl-1H-pyrazol-3-one

CAS Registry Number

89-25-8

SMILES

CC1=CC(=O)N(N1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-7,11H,1H3

InChI Key

KZQYIMCESJLPQH-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azoles

Sub Class

Pyrazoles

Direct Parent

Phenylpyrazoles

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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0006240)
Extracellular (HMDB: HMDB0006240)

Source

Exogenous

Exogenous (HMDB: HMDB0006240)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0006240)

Process

Not Available

Role

Biological role

Drug metabolite (HMDB: HMDB0006240)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	130 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	380.9 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	19.3 g/L	ALOGPS
logP	0.59	ALOGPS
logP	1.28	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Acidic)	8.27	ChemAxon
pKa (Strongest Basic)	1.62	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.34 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	62.14 m³·mol⁻¹	ChemAxon
Polarizability	18.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	140.119	31661259
DarkChem	[M-H]-	138.925	31661259
DeepCCS	[M+H]+	137.187	30932474
DeepCCS	[M-H]-	134.791	30932474
DeepCCS	[M-2H]-	169.703	30932474
DeepCCS	[M+Na]+	144.162	30932474
AllCCS	[M+H]+	136.4	32859911
AllCCS	[M+H-H2O]+	131.9	32859911
AllCCS	[M+NH4]+	140.6	32859911
AllCCS	[M+Na]+	141.8	32859911
AllCCS	[M-H]-	137.2	32859911
AllCCS	[M+Na-2H]-	137.6	32859911
AllCCS	[M+HCOO]-	138.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Demethylated antipyrine	CC1=CC(=O)N(N1)C1=CC=CC=C1	2548.8	Standard polar	33892256
Demethylated antipyrine	CC1=CC(=O)N(N1)C1=CC=CC=C1	1684.9	Standard non polar	33892256
Demethylated antipyrine	CC1=CC(=O)N(N1)C1=CC=CC=C1	1685.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Demethylated antipyrine,1TMS,isomer #1	CC1=CC(=O)N(C2=CC=CC=C2)N1[Si](C)(C)C	1687.8	Semi standard non polar	33892256
Demethylated antipyrine,1TMS,isomer #1	CC1=CC(=O)N(C2=CC=CC=C2)N1[Si](C)(C)C	1820.6	Standard non polar	33892256
Demethylated antipyrine,1TMS,isomer #1	CC1=CC(=O)N(C2=CC=CC=C2)N1[Si](C)(C)C	2159.1	Standard polar	33892256
Demethylated antipyrine,1TBDMS,isomer #1	CC1=CC(=O)N(C2=CC=CC=C2)N1[Si](C)(C)C(C)(C)C	1923.0	Semi standard non polar	33892256
Demethylated antipyrine,1TBDMS,isomer #1	CC1=CC(=O)N(C2=CC=CC=C2)N1[Si](C)(C)C(C)(C)C	2031.1	Standard non polar	33892256
Demethylated antipyrine,1TBDMS,isomer #1	CC1=CC(=O)N(C2=CC=CC=C2)N1[Si](C)(C)C(C)(C)C	2241.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Demethylated antipyrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-4900000000-e7fde844e072d094e7bf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Demethylated antipyrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Demethylated antipyrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylated antipyrine 10V, Positive-QTOF	splash10-004i-0900000000-ccca975ba1e597027ed5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylated antipyrine 20V, Positive-QTOF	splash10-004i-0900000000-96da0ec122d8a8403486	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylated antipyrine 40V, Positive-QTOF	splash10-0a4r-9500000000-905aac7834f5ebcbec59	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylated antipyrine 10V, Negative-QTOF	splash10-00di-0900000000-8e7cd9ae2599cec8be88	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylated antipyrine 20V, Negative-QTOF	splash10-00di-0900000000-dbe1b04ba8ec0bb7b01a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylated antipyrine 40V, Negative-QTOF	splash10-054k-6900000000-e3078766e74d43ea5dce	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylated antipyrine 10V, Positive-QTOF	splash10-004i-0900000000-99e013a33d61f5b2babb	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylated antipyrine 20V, Positive-QTOF	splash10-004i-0900000000-96887c840d6d9faeba92	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylated antipyrine 40V, Positive-QTOF	splash10-004i-9100000000-a5215b963ef8a7e94117	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylated antipyrine 10V, Negative-QTOF	splash10-00di-0900000000-6c988551b42e630dedc7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylated antipyrine 20V, Negative-QTOF	splash10-00xr-9600000000-0d26a32aab574f87a282	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Demethylated antipyrine 40V, Negative-QTOF	splash10-00kf-9100000000-89d891f53ac7bcc51cdb	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023854

KNApSAcK ID

Not Available

Chemspider ID

63516

KEGG Compound ID

C13008

BioCyc ID

Not Available

BiGG ID

2299979

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

70335

PDB ID

Not Available

ChEBI ID

31530

Food Biomarker Ontology

Not Available

VMH ID

DMANTIPYRINE

MarkerDB ID

Not Available

Good Scents ID

rw1191581

References

Synthesis Reference

Rojahn, C. A. 1-Alkyl-3-chloropyrazoles and 1-alkyl-3-pyrazolones. Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1922), 55B 2959-71. CODEN: BDCBAD ISSN:0365-9488. CAN 17:6867 AN 1923:6867 CAPLUS

Material Safety Data Sheet (MSDS)

Not Available

General References

Yoshida H, Yanai H, Namiki Y, Fukatsu-Sasaki K, Furutani N, Tada N: Neuroprotective effects of edaravone: a novel free radical scavenger in cerebrovascular injury. CNS Drug Rev. 2006 Spring;12(1):9-20. [PubMed:16834755 ]

Showing metabocard for Demethylated antipyrine (HMDB0006240)

MOL for HMDB0006240 (Demethylated antipyrine)

3D MOL for HMDB0006240 (Demethylated antipyrine)

3D SDF for HMDB0006240 (Demethylated antipyrine)

3D-SDF for HMDB0006240 (Demethylated antipyrine)

PDB for HMDB0006240 (Demethylated antipyrine)

3D PDB for HMDB0006240 (Demethylated antipyrine)

SMILES for HMDB0006240 (Demethylated antipyrine)

INCHI for HMDB0006240 (Demethylated antipyrine)

Structure for HMDB0006240 (Demethylated antipyrine)

3D Structure for HMDB0006240 (Demethylated antipyrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra