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Showing metabocard for Demethylated antipyrine (HMDB0006240)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 18:56:27 UTC
Update Date2023-02-21 17:17:16 UTC
HMDB IDHMDB0006240
Secondary Accession Numbers
  • HMDB06240
Metabolite Identification
Common NameDemethylated antipyrine
DescriptionDemethylated 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
Data?1676999836
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0006240 (Demethylated antipyrine)


  Mrv0541 02231220342D          

 13 14  0  0  0  0            999 V2000
   15.9315  -11.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6459  -11.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6459  -12.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9315  -13.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2170  -12.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2170  -11.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9315  -10.7401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2640  -10.2551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5989  -10.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3440   -9.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5190   -9.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0340   -8.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3835  -10.5101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  6  1  1  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 11  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  2  0  0  0  0
M  END
Download

3D MOL for HMDB0006240 (Demethylated antipyrine)

HMDB0006240
     RDKit          3D
Demethylated antipyrine
 23 24  0  0  0  0  0  0  0  0999 V2000
    3.8328   -0.8557   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5353   -0.1953    0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3974    0.9636    0.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0381    1.2287    0.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4695    2.1854    1.3505 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4001    0.2517    0.0962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0054    0.1439   -0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6658    0.8519   -1.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0347    0.7308   -1.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7936   -0.1031   -0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1334   -0.8113    0.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7628   -0.6908    0.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846   -0.5885   -0.3603 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3171   -0.3709   -1.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6470   -1.9342   -0.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5482   -0.7743    0.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2018    1.5311    1.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0539    1.5136   -1.7209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5373    1.2976   -2.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8668   -0.2057   -0.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7109   -1.4759    1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2290   -1.2471    1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1217   -1.4458   -0.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13  2  1  0
 12  7  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
 13 23  1  0
M  END
Download

3D SDF for HMDB0006240 (Demethylated antipyrine)


  Mrv0541 02231220342D          

 13 14  0  0  0  0            999 V2000
   15.9315  -11.5651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6459  -11.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6459  -12.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9315  -13.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2170  -12.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2170  -11.9776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9315  -10.7401    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2640  -10.2551    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5989  -10.2551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3440   -9.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5190   -9.4705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0340   -8.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3835  -10.5101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  6  1  1  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 11  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006240

> <DATABASE_NAME>
hmdb

> <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

> <FORMULA>
C10H10N2O

> <MOLECULAR_WEIGHT>
174.1992

> <EXACT_MASS>
174.079312952

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
18.553654761584852

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.59

> <JCHEM_LOGP>
1.276877759333333

> <ALOGPS_LOGS>
-0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.266748606708767

> <JCHEM_PKA_STRONGEST_BASIC>
1.619044482553643

> <JCHEM_POLAR_SURFACE_AREA>
32.34

> <JCHEM_REFRACTIVITY>
62.13500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methyl-2-phenyl-1H-pyrazol-3-one

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0006240 (Demethylated antipyrine)

HMDB0006240
     RDKit          3D
Demethylated antipyrine
 23 24  0  0  0  0  0  0  0  0999 V2000
    3.8328   -0.8557   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5353   -0.1953    0.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3974    0.9636    0.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0381    1.2287    0.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4695    2.1854    1.3505 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4001    0.2517    0.0962 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0054    0.1439   -0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6658    0.8519   -1.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0347    0.7308   -1.2738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7936   -0.1031   -0.4787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1334   -0.8113    0.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7628   -0.6908    0.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2846   -0.5885   -0.3603 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3171   -0.3709   -1.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6470   -1.9342   -0.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5482   -0.7743    0.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2018    1.5311    1.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0539    1.5136   -1.7209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5373    1.2976   -2.0544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8668   -0.2057   -0.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7109   -1.4759    1.1444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2290   -1.2471    1.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1217   -1.4458   -0.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  6 13  1  0
 13  2  1  0
 12  7  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
 11 21  1  0
 12 22  1  0
 13 23  1  0
M  END
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PDB for HMDB0006240 (Demethylated antipyrine)

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
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3D PDB for HMDB0006240 (Demethylated antipyrine)

COMPND    HMDB0006240
HETATM    1  C1  UNL     1       3.833  -0.856  -0.286  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.535  -0.195   0.015  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.397   0.964   0.749  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.038   1.229   0.788  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.469   2.185   1.351  1.00  0.00           O  
HETATM    6  N1  UNL     1       0.400   0.252   0.096  1.00  0.00           N  
HETATM    7  C5  UNL     1      -1.005   0.144  -0.110  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.666   0.852  -1.092  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.035   0.731  -1.274  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.794  -0.103  -0.479  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.133  -0.811   0.504  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.763  -0.691   0.687  1.00  0.00           C  
HETATM   13  N2  UNL     1       1.285  -0.589  -0.360  1.00  0.00           N  
HETATM   14  H1  UNL     1       4.317  -0.371  -1.173  1.00  0.00           H  
HETATM   15  H2  UNL     1       3.647  -1.934  -0.461  1.00  0.00           H  
HETATM   16  H3  UNL     1       4.548  -0.774   0.573  1.00  0.00           H  
HETATM   17  H4  UNL     1       3.202   1.531   1.193  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.054   1.514  -1.721  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.537   1.298  -2.054  1.00  0.00           H  
HETATM   20  H7  UNL     1      -4.867  -0.206  -0.612  1.00  0.00           H  
HETATM   21  H8  UNL     1      -3.711  -1.476   1.144  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.229  -1.247   1.463  1.00  0.00           H  
HETATM   23  H10 UNL     1       1.122  -1.446  -0.929  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3   13
CONECT    3    4   17
CONECT    4    5    5    6
CONECT    6    7   13
CONECT    7    8    8   12
CONECT    8    9   18
CONECT    9   10   10   19
CONECT   10   11   20
CONECT   11   12   12   21
CONECT   12   22
CONECT   13   23
END
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SMILES for HMDB0006240 (Demethylated antipyrine)

CC1=CC(=O)N(N1)C1=CC=CC=C1
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INCHI for HMDB0006240 (Demethylated antipyrine)

InChI=1S/C10H10N2O/c1-8-7-10(13)12(11-8)9-5-3-2-4-6-9/h2-7,11H,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
1-Phenyl-3-methyl-1H-4,5-dihydropyrazol-5-oneHMDB
1-Phenyl-3-methyl-2-pyrazolin-5-oneHMDB
1-Phenyl-3-methyl-5-oxopyrazoleHMDB
1-Phenyl-3-methyl-5-pyrazolinoneHMDB
1-Phenyl-3-methyl-5-pyrazoloneHMDB
2,4-dihydro-5-Methyl-2-phenyl-3H-pyrazol-3-oneHMDB
3-Methyl-1-phenyl-1H-pyrazol-5-oneHMDB
3-Methyl-1-phenyl-2-pyrazolin-5-oneHMDB
3-Methyl-1-phenyl-2-pyrazoline-5-oneHMDB
3-Methyl-1-phenyl-4,5-dihydropyrazol-5-oneHMDB
3-Methyl-1-phenyl-4,5-dihydropyrazole-5-oneHMDB
3-Methyl-1-phenyl-5-pyrazoloneHMDB
3-Methyl-1-phenylpyrazol-5(4H)-oneHMDB
3-Methyl-1-phenylpyrazolin-5-oneHMDB
5-Methyl-2-phenyl-2H-pyrazol-3(4H)-oneHMDB
5-Methyl-2-phenylpyrazol-3-oneHMDB
EdaraboneHMDB
EdaravoneHMDB
MethylphenylpyrazoloneHMDB
NorantipyrineHMDB
NorphenazoneHMDB
N-Demethylantipyrine, 14C-labeledMeSH, HMDB
N-DemethylantipyrineMeSH, HMDB
Chemical FormulaC10H10N2O
Average Molecular Weight174.1992
Monoisotopic Molecular Weight174.079312952
IUPAC Name5-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
Traditional Name5-methyl-2-phenyl-1H-pyrazol-3-one
CAS Registry Number89-25-8
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 KeyKZQYIMCESJLPQH-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point130 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility380.9 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility19.3 g/LALOGPS
logP0.59ALOGPS
logP1.28ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)8.27ChemAxon
pKa (Strongest Basic)1.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.34 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity62.14 m³·mol⁻¹ChemAxon
Polarizability18.55 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]+140.11931661259
DarkChem[M-H]-138.92531661259
DeepCCS[M+H]+137.18730932474
DeepCCS[M-H]-134.79130932474
DeepCCS[M-2H]-169.70330932474
DeepCCS[M+Na]+144.16230932474
AllCCS[M+H]+136.432859911
AllCCS[M+H-H2O]+131.932859911
AllCCS[M+NH4]+140.632859911
AllCCS[M+Na]+141.832859911
AllCCS[M-H]-137.232859911
AllCCS[M+Na-2H]-137.632859911
AllCCS[M+HCOO]-138.032859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.4.63 minutes32390414
Predicted by Siyang on May 30, 20229.3253 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.04 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid721.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid310.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid112.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid172.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid63.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid279.8 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 Acid294.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)375.0 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid676.2 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid169.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid741.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid186.9 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid252.7 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate415.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA331.4 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water118.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Demethylated antipyrineCC1=CC(=O)N(N1)C1=CC=CC=C12548.8Standard polar33892256
Demethylated antipyrineCC1=CC(=O)N(N1)C1=CC=CC=C11684.9Standard non polar33892256
Demethylated antipyrineCC1=CC(=O)N(N1)C1=CC=CC=C11685.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Demethylated antipyrine,1TMS,isomer #1CC1=CC(=O)N(C2=CC=CC=C2)N1[Si](C)(C)C1687.8Semi standard non polar33892256
Demethylated antipyrine,1TMS,isomer #1CC1=CC(=O)N(C2=CC=CC=C2)N1[Si](C)(C)C1820.6Standard non polar33892256
Demethylated antipyrine,1TMS,isomer #1CC1=CC(=O)N(C2=CC=CC=C2)N1[Si](C)(C)C2159.1Standard polar33892256
Demethylated antipyrine,1TBDMS,isomer #1CC1=CC(=O)N(C2=CC=CC=C2)N1[Si](C)(C)C(C)(C)C1923.0Semi standard non polar33892256
Demethylated antipyrine,1TBDMS,isomer #1CC1=CC(=O)N(C2=CC=CC=C2)N1[Si](C)(C)C(C)(C)C2031.1Standard non polar33892256
Demethylated antipyrine,1TBDMS,isomer #1CC1=CC(=O)N(C2=CC=CC=C2)N1[Si](C)(C)C(C)(C)C2241.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Demethylated antipyrine GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-4900000000-e7fde844e072d094e7bf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Demethylated antipyrine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Demethylated antipyrine 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 - Demethylated antipyrine 10V, Positive-QTOFsplash10-004i-0900000000-ccca975ba1e597027ed52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylated antipyrine 20V, Positive-QTOFsplash10-004i-0900000000-96da0ec122d8a84034862017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylated antipyrine 40V, Positive-QTOFsplash10-0a4r-9500000000-905aac7834f5ebcbec592017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylated antipyrine 10V, Negative-QTOFsplash10-00di-0900000000-8e7cd9ae2599cec8be882017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylated antipyrine 20V, Negative-QTOFsplash10-00di-0900000000-dbe1b04ba8ec0bb7b01a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylated antipyrine 40V, Negative-QTOFsplash10-054k-6900000000-e3078766e74d43ea5dce2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylated antipyrine 10V, Positive-QTOFsplash10-004i-0900000000-99e013a33d61f5b2babb2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylated antipyrine 20V, Positive-QTOFsplash10-004i-0900000000-96887c840d6d9faeba922021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylated antipyrine 40V, Positive-QTOFsplash10-004i-9100000000-a5215b963ef8a7e941172021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylated antipyrine 10V, Negative-QTOFsplash10-00di-0900000000-6c988551b42e630dedc72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylated antipyrine 20V, Negative-QTOFsplash10-00xr-9600000000-0d26a32aab574f87a2822021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylated antipyrine 40V, Negative-QTOFsplash10-00kf-9100000000-89d891f53ac7bcc51cdb2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023854
KNApSAcK IDNot Available
Chemspider ID63516
KEGG Compound IDC13008
BioCyc IDNot Available
BiGG ID2299979
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound70335
PDB IDNot Available
ChEBI ID31530
Food Biomarker OntologyNot Available
VMH IDDMANTIPYRINE
MarkerDB IDNot Available
Good Scents IDrw1191581
References
Synthesis ReferenceRojahn, 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)Download (PDF)
General References
  1. 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 ]