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Showing NP-Card for antipyrine (NP0264814)

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Record Information
Version2.0
Created at2022-09-08 08:34:20 UTC
Updated at2022-09-08 08:34:20 UTC
NP-MRD IDNP0264814
Secondary Accession NumbersNone
Natural Product 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. Antipyrine is an extremely weak basic (essentially neutral) compound (based on its pKa). In humans, antipyrine is involved in antipyrine action pathway. antipyrine is found in Homo sapiens. antipyrine was first documented in 2014 (PMID: 24345239). A pyrazolone derivative that is 1,2-dihydropyrazol-3-one substituted with methyl groups at C-1 and C-5 and with a phenyl group at N-2 (PMID: 25038548) (PMID: 25435228) (PMID: 25631541) (PMID: 26703262).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0264814 (antipyrine)

1435
  Mrv0541 02231215292D          

 14 15  0  0  1  0            999 V2000
    1.6500    0.4990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021    0.2690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695    0.7540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5146    1.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021   -0.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    0.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896    1.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5541    0.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9995    2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -0.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3876   -0.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -1.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3876   -1.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021   -2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  7  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  2  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  2  0  0  0  0
 12 14  2  0  0  0  0
 13 14  1  0  0  0  0
M  END
Download

3D MOL for NP0264814 (antipyrine)

     RDKit          3D

 26 27  0  0  0  0  0  0  0  0999 V2000
   -3.7926    0.3415    0.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4447   -0.2188   -0.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1851   -1.3416   -1.0897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8193   -1.4925   -1.1260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1457   -2.3779   -1.7247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2671   -0.5066   -0.3909 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1264   -0.2879   -0.1612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8913   -1.1307    0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2161   -0.9692    0.8701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8683    0.1115    0.3118 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1398    0.9960   -0.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860    0.7961   -0.7197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2496    0.2370    0.0899 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0261    1.4060    0.9388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4453   -0.5507    0.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2315    0.9104   -0.7926 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7350    0.9005    0.9905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9133   -1.9665   -1.5754 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3796   -1.9760    1.0564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8197   -1.6272    1.4818 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9303    0.2622    0.4977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6908    1.8317   -0.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2690    1.4906   -1.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9184    1.6781    1.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2066    1.2058    1.6552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7368    2.2784    0.3100 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13  6  1  0
  6  4  1  0
  4  5  2  0
  4  3  1  0
  3  2  2  0
  2  1  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
  2 13  1  0
 12  7  1  0
 14 24  1  0
 14 25  1  0
 14 26  1  0
  3 18  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
 11 22  1  0
 12 23  1  0
M  END
Download

3D SDF for NP0264814 (antipyrine)

1435
  Mrv0541 02231215292D          

 14 15  0  0  1  0            999 V2000
    1.6500    0.4990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021    0.2690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7695    0.7540    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5146    1.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021   -0.5560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4347    0.7540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6896    1.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5541    0.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9995    2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -0.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3876   -0.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8166   -1.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3876   -1.7935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1021   -2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  7  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  2  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
 10 12  1  0  0  0  0
 11 13  2  0  0  0  0
 12 14  2  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0264814

> <DATABASE_NAME>
NP-MRD

> <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_KEY>
VEQOALNAAJBPNY-UHFFFAOYSA-N

> <FORMULA>
C11H12N2O

> <MOLECULAR_WEIGHT>
188.2258

> <EXACT_MASS>
188.094963016

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
20.403569601512736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.18

> <JCHEM_LOGP>
1.2189718436666666

> <ALOGPS_LOGS>
-0.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.3706652076238215

> <JCHEM_POLAR_SURFACE_AREA>
23.550000000000004

> <JCHEM_REFRACTIVITY>
56.41680000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.74e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
antipyrine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0264814 (antipyrine)

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PDB for NP0264814 (antipyrine)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1435                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080   0.931   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       5.791   0.502   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       7.036   1.407   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       6.561   2.872   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.791  -1.038   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.545   1.407   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.021   2.872   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.501   0.931   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.466   4.118   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.124  -1.808   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.457  -1.808   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.124  -3.348   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.457  -3.348   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.791  -4.118   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    3    5    6                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    7    9                                                  
CONECT    5    2   10   11                                                  
CONECT    6    1    2    7                                                  
CONECT    7    4    6                                                       
CONECT    8    3                                                            
CONECT    9    4                                                            
CONECT   10    5   12                                                       
CONECT   11    5   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   14                                                       
CONECT   14   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for NP0264814 (antipyrine)
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SMILES for NP0264814 (antipyrine)
CN1N(C(=O)C=C1C)C1=CC=CC=C1
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INCHI for NP0264814 (antipyrine)
InChI=1S/C11H12N2O/c1-9-8-11(14)13(12(9)2)10-6-4-3-5-7-10/h3-8H,1-2H3
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View in JSmol
Synonyms
ValueSource
1,2-Dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-oneChEBI
2,3-Dimethyl-1-phenyl-5-pyrazoloneChEBI
FenazonaChEBI
PhenazoneChEBI
AnalgesineHMDB
AnodyninHMDB
AnodynineHMDB
AntipirinHMDB
AntipyrinHMDB
AntipyrinumHMDB
AzophenHMDB
AzophenumHMDB
FenazoneHMDB
PhenozoneHMDB
PyramidoneHMDB
Chemical FormulaC11H12N2O
Average Mass188.2258 Da
Monoisotopic Mass188.09496 Da
IUPAC Name1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one
Traditional Nameantipyrine
CAS Registry NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Homo sapiensLOTUS Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0015503  
DrugBank IDDB01435  
Phenol Explorer Compound IDNot Available
FoodDB 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  
Good Scents IDNot Available
References
General References
  1. Espejo A, Aguinaco A, Amat AM, Beltran FJ: Some ozone advanced oxidation processes to improve the biological removal of selected pharmaceutical contaminants from urban wastewater. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2014;49(4):410-21. doi:  10.1080/10934529.2014.854652. [PubMed:24345239  ] 
  2. Miao HF, Cao M, Xu DY, Ren HY, Zhao MX, Huang ZX, Ruan WQ: Degradation of phenazone in aqueous solution with ozone: influencing factors and degradation pathways. Chemosphere. 2015 Jan;119:326-333. doi: 10.1016/j.chemosphere.2014.06.082. Epub  2014 Jul 17. [PubMed:25038548  ] 
  3. Bulatov A, Medinskaia K, Aseeva D, Garmonov S, Moskvin L: Determination of antipyrine in saliva using the dispersive liquid-liquid microextraction based on a stepwise injection system. Talanta. 2015 Feb;133:66-70. doi: 10.1016/j.talanta.2014.05.064. Epub 2014 Jul 8. [PubMed:25435228  ] 
  4. Karinen R, Hoiseth G, Svendsen KO, Rogde S, Vindenes V: A fatal intoxication with phenazone (antipyrine). Forensic Sci Int. 2015 Mar;248:e13-5. doi: 10.1016/j.forsciint.2015.01.001. Epub  2015 Jan 8. [PubMed:25631541  ] 
  5. Medinskaia K, Vakh C, Aseeva D, Andruch V, Moskvin L, Bulatov A: A fully automated effervescence assisted dispersive liquid-liquid microextraction based on a stepwise injection system. Determination of antipyrine in saliva samples. Anal Chim Acta. 2016 Jan 1;902:129-134. doi: 10.1016/j.aca.2015.11.017. Epub 2015  Nov 27. [PubMed:26703262  ] 
  6. LOTUS database [Link]