NP-MRD: Showing NP-Card for 4-Aminoantipyrine (NP0002631)

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Record Information

Version

1.0

Created at

2020-11-23 18:25:39 UTC

Updated at

2021-08-19 23:59:13 UTC

NP-MRD ID

NP0002631

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Aminoantipyrine

Provided By

BMRB

Description

4-Aminoantipyrine, also known as 4-AAP or 4-aminophenazone, 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. 4-Aminoantipyrine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. It was first documented in 2008 (PMID: 17984079). Based on a literature review a significant number of articles have been published on 4-Aminoantipyrine (PMID: 24056243) (PMID: 24508878) (PMID: 25476354) (PMID: 25652276).

Structure

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


     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   -3.6242    0.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566    0.1959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2605   -1.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4151   -2.2587    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8072   -1.6722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2532   -3.0662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0051   -0.4047    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4919   -0.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3236   -1.5569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8205   -1.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4857   -0.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6540    1.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1571    1.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9627    0.7499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5915    2.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4263   -0.2695    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9825    2.3538    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8917    1.8001    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1630   -3.7373    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8217   -1.7376    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583   -2.9013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6522   -2.7091    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9826   -0.0202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3192    2.4764    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6117    2.1216    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9888    2.7488    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6136    2.0483    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2204    3.6566    0.0000 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  7 14  1  0
 14 15  1  0
 14  2  1  0
 13  8  1  0
  1 16  1  6
  1 17  1  0
  1 18  1  0
  4 19  1  0
  4 20  1  0
  9 21  1  0
 10 22  1  0
 11 23  1  0
 12 24  1  0
 13 25  1  0
 15 26  1  1
 15 27  1  0
 15 28  1  0
M  END
> <DATABASE_ID>
NP0002631

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1N(C(=O)C(N)=C1C)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H13N3O/c1-8-10(12)11(15)14(13(8)2)9-6-4-3-5-7-9/h3-7H,12H2,1-2H3

> <INCHI_KEY>
RLFWWDJHLFCNIJ-UHFFFAOYSA-N

> <FORMULA>
C11H13N3O

> <MOLECULAR_WEIGHT>
203.245

> <EXACT_MASS>
203.105862051

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.868823487642306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.84

> <JCHEM_LOGP>
0.33496658466666696

> <ALOGPS_LOGS>
-0.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.0696218784018321

> <JCHEM_POLAR_SURFACE_AREA>
49.57000000000001

> <JCHEM_REFRACTIVITY>
60.04170000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.29e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aminoantipyrine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.009  -5.926   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       0.564  -4.680   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       0.088  -3.215   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.377  -2.739   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.342  -5.926   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.285  -7.333   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.620  -8.578   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.152  -8.417   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.778  -7.011   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.873  -5.765   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.044  -2.739   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    9                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15    3                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    NP0002631
HETATM    1  C1  UNL     1       3.400  -0.512   0.899  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.169  -0.002   0.238  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.122   0.950  -0.764  1.00  0.00           C  
HETATM    4  N1  UNL     1       3.203   1.625  -1.359  1.00  0.00           N  
HETATM    5  C4  UNL     1       0.782   1.097  -1.056  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.247   1.853  -1.902  1.00  0.00           O  
HETATM    7  N2  UNL     1       0.045   0.268  -0.263  1.00  0.00           N  
HETATM    8  C5  UNL     1      -1.367   0.123  -0.257  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.114  -0.017   0.892  1.00  0.00           C  
HETATM   10  C7  UNL     1      -3.486  -0.156   0.873  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.161  -0.158  -0.329  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.447  -0.021  -1.484  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.072   0.117  -1.439  1.00  0.00           C  
HETATM   14  N3  UNL     1       0.908  -0.380   0.504  1.00  0.00           N  
HETATM   15  C11 UNL     1       0.534  -1.376   1.509  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.297  -0.284   0.285  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.280  -1.574   1.115  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.503   0.018   1.890  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.351   2.634  -1.061  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.847   1.180  -2.063  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.649  -0.024   1.863  1.00  0.00           H  
HETATM   22  H7  UNL     1      -4.086  -0.268   1.769  1.00  0.00           H  
HETATM   23  H8  UNL     1      -5.254  -0.270  -0.335  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.972  -0.022  -2.428  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.548   0.222  -2.360  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.467  -0.948   2.517  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.365  -1.946   1.198  1.00  0.00           H  
HETATM   28  H13 UNL     1       1.366  -2.130   1.550  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3   14
CONECT    3    4    5
CONECT    4   19   20
CONECT    5    6    6    7
CONECT    7    8   14
CONECT    8    9    9   13
CONECT    9   10   21
CONECT   10   11   11   22
CONECT   11   12   23
CONECT   12   13   13   24
CONECT   13   25
CONECT   14   15
CONECT   15   26   27   28
END

View in JSmol

Synonyms

Value	Source
4-AAP	ChEBI
4-Amino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one	ChEBI
4-Aminoantipyrene	ChEBI
4-Aminophenazone	ChEBI
Aminoantipyrin	ChEBI
Aminoantipyrine	ChEBI
Aminoazophenazone	ChEBI
Aminoazophene	ChEBI
Ampyrone	ChEBI
Metapirazone	ChEBI
Solnapyrin-a	ChEBI
Solvapyrin-a	ChEBI
4 Aminophenazone	HMDB
4 Aminoantipyrine	HMDB
4-Amino-1,5-dimethyl-2-phenyl-3H-pyrazolone	HMDB
4 Amino 1,5 dimethyl 2 phenyl 3H pyrazolone	HMDB

Chemical Formula

C₁₁H₁₃N₃O

Average Mass

203.2450 Da

Monoisotopic Mass

203.10586 Da

IUPAC Name

4-amino-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one

Traditional Name

aminoantipyrine

CAS Registry Number

Not Available

SMILES

CN1N(C(=O)C(N)=C1C)C1=CC=CC=C1

InChI Identifier

InChI=1S/C11H13N3O/c1-8-10(12)11(15)14(13(8)2)9-6-4-3-5-7-9/h3-7H,12H2,1-2H3

InChI Key

RLFWWDJHLFCNIJ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	109.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	308.96 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	2379 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	-0.257 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	0.84	ALOGPS
logP	0.33	ChemAxon
logS	-0.79	ALOGPS
pKa (Strongest Basic)	0.07	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.57 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	60.04 m³·mol⁻¹	ChemAxon
Polarizability	21.87 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0246350

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2066

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ampyrone

METLIN ID

Not Available

PubChem Compound

2151

PDB ID

Not Available

ChEBI ID

59026

Good Scents ID

rw1198741

References

General References

Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
Teng Y, Liu R: Insights into potentially toxic effects of 4-aminoantipyrine on the antioxidant enzyme copper-zinc superoxide dismutase. J Hazard Mater. 2013 Nov 15;262:318-24. doi: 10.1016/j.jhazmat.2013.08.047. Epub 2013 Aug 28. [PubMed:24056243 ]
Gowda JI, Nandibewoor ST: Binding and conformational changes of human serum albumin upon interaction with 4-aminoantipyrine studied by spectroscopic methods and cyclic voltammetry. Spectrochim Acta A Mol Biomol Spectrosc. 2014 Apr 24;124:397-403. doi: 10.1016/j.saa.2014.01.028. Epub 2014 Jan 21. [PubMed:24508878 ]
Kim HY, Lee HJ, Chang SK: Reaction-based colorimetric signaling of Cu(2+) ions by oxidative coupling of phenols with 4-aminoantipyrine. Talanta. 2015 Jan;132:625-9. doi: 10.1016/j.talanta.2014.09.048. Epub 2014 Oct 14. [PubMed:25476354 ]
Mnguni MJ, Lemmerer A: A structural study of 4-aminoantipyrine and six of its Schiff base derivatives. Acta Crystallogr C Struct Chem. 2015 Feb;71(Pt 2):103-9. doi: 10.1107/S2053229614027247. Epub 2015 Jan 12. [PubMed:25652276 ]

Showing NP-Card for 4-Aminoantipyrine (NP0002631)

MOL for NP0002631 (4-Aminoantipyrine)

3D MOL for NP0002631 (4-Aminoantipyrine)

3D SDF for NP0002631 (4-Aminoantipyrine)

3D-SDF for NP0002631 (4-Aminoantipyrine)

PDB for NP0002631 (4-Aminoantipyrine)

3D PDB for NP0002631 (4-Aminoantipyrine)

SMILES for NP0002631 (4-Aminoantipyrine)

INCHI for NP0002631 (4-Aminoantipyrine)

Structure for NP0002631 (4-Aminoantipyrine)

3D Structure for NP0002631 (4-Aminoantipyrine)