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Showing NP-Card for 4-Nitrocatechol (NP0002671)

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Record Information
Version2.0
Created at2020-11-23 18:26:32 UTC
Updated at2021-08-12 19:51:49 UTC
NP-MRD IDNP0002671
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Nitrocatechol
Provided ByBMRBBMRB logo
Description4-Nitrocatechol belongs to the class of organic compounds known as nitrophenols. Nitrophenols are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms. 4-Nitrocatechol exists in all living organisms, ranging from bacteria to humans. 4-Nitrocatechol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. 4-Nitrocatechol was first documented in 1993 (PMID: 8267647). Based on a literature review a small amount of articles have been published on 4-Nitrocatechol (PMID: 8214571) (PMID: 14993710) (PMID: 20854995).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002671 (4-Nitrocatechol)


     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
   -3.0766   -2.0432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7723   -0.5744    0.0000 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.8921    0.4235    0.0000 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.3481   -0.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0438    1.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3804    1.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5003    0.8380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9245    1.3088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1959   -0.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3158   -1.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2283   -1.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1636    2.3631    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6848    3.3048    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0443    0.3109    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0114   -3.0975    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5326   -2.5704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11  4  1  0
  5 12  1  0
  6 13  1  0
  8 14  1  0
 10 15  1  0
 11 16  1  0
M  CHG  2   2   1   3  -1
M  END
Download

3D MOL for NP0002671 (4-Nitrocatechol)

NP0002671
     RDKit          3D

 16 16  0  0  0  0  0  0  0  0999 V2000
   -3.4630   -0.8296   -0.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6501    0.0449    0.1960 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.1537    1.2011    0.7326 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2551   -0.1353    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7517   -1.3045   -0.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6112   -1.4530   -0.6729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4772   -0.4236   -0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8470   -0.5776   -0.4409 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9652    0.7385    0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8603    1.7350    0.6311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3997    0.8701    0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979   -2.1161   -0.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0380   -2.3514   -1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4530    0.1785   -0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5791    2.6119    1.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7599    1.8111    0.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11  4  1  0
  5 12  1  0
  6 13  1  0
  8 14  1  0
 10 15  1  0
 11 16  1  0
M  CHG  2   2   1   3  -1
M  END
Download

3D SDF for NP0002671 (4-Nitrocatechol)


     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
   -3.0766   -2.0432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7723   -0.5744    0.0000 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.8921    0.4235    0.0000 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.3481   -0.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0438    1.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3804    1.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5003    0.8380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9245    1.3088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1959   -0.6308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3158   -1.6287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2283   -1.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1636    2.3631    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6848    3.3048    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0443    0.3109    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0114   -3.0975    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5326   -2.5704    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11  4  1  0
  5 12  1  0
  6 13  1  0
  8 14  1  0
 10 15  1  0
 11 16  1  0
M  CHG  2   2   1   3  -1
M  END
> <DATABASE_ID>
NP0002671

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(O)C=C(C=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H5NO4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H

> <INCHI_KEY>
XJNPNXSISMKQEX-UHFFFAOYSA-N

> <FORMULA>
C6H5NO4

> <MOLECULAR_WEIGHT>
155.1082

> <EXACT_MASS>
155.021857653

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
13.118485427435335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-nitrobenzene-1,2-diol

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
1.3060993619999999

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.832111468042104

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.177205174323545

> <JCHEM_PKA_STRONGEST_BASIC>
-6.433192237604282

> <JCHEM_POLAR_SURFACE_AREA>
83.6

> <JCHEM_REFRACTIVITY>
36.3403

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.76e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-nitrocatechol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002671 (4-Nitrocatechol)

NP0002671
     RDKit          3D

 16 16  0  0  0  0  0  0  0  0999 V2000
   -3.4630   -0.8296   -0.1304 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6501    0.0449    0.1960 N   0  0  0  0  0  4  0  0  0  0  0  0
   -3.1537    1.2011    0.7326 O   0  0  0  0  0  1  0  0  0  0  0  0
   -1.2551   -0.1353    0.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7517   -1.3045   -0.5176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6112   -1.4530   -0.6729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4772   -0.4236   -0.2827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8470   -0.5776   -0.4409 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9652    0.7385    0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8603    1.7350    0.6311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3997    0.8701    0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3979   -2.1161   -0.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0380   -2.3514   -1.0923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4530    0.1785   -0.1522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5791    2.6119    1.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7599    1.8111    0.8387 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11  4  1  0
  5 12  1  0
  6 13  1  0
  8 14  1  0
 10 15  1  0
 11 16  1  0
M  CHG  2   2   1   3  -1
M  END
Download

PDB for NP0002671 (4-Nitrocatechol)

HEADER    PROTEIN                                 16-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-18         0                                  
HETATM    1  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+1
HETATM    9  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    2                                                       
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    3                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0002671 (4-Nitrocatechol)

COMPND    NP0002671
HETATM    1  O1  UNL     1      -3.463  -0.830  -0.130  1.00  0.00           O  
HETATM    2  N1  UNL     1      -2.650   0.045   0.196  1.00  0.00           N1+
HETATM    3  O2  UNL     1      -3.154   1.201   0.733  1.00  0.00           O1-
HETATM    4  C1  UNL     1      -1.255  -0.135   0.025  1.00  0.00           C  
HETATM    5  C2  UNL     1      -0.752  -1.304  -0.518  1.00  0.00           C  
HETATM    6  C3  UNL     1       0.611  -1.453  -0.673  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.477  -0.424  -0.283  1.00  0.00           C  
HETATM    8  O3  UNL     1       2.847  -0.578  -0.441  1.00  0.00           O  
HETATM    9  C5  UNL     1       0.965   0.739   0.257  1.00  0.00           C  
HETATM   10  O4  UNL     1       1.860   1.735   0.631  1.00  0.00           O  
HETATM   11  C6  UNL     1      -0.400   0.870   0.405  1.00  0.00           C  
HETATM   12  H1  UNL     1      -1.398  -2.116  -0.828  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.038  -2.351  -1.092  1.00  0.00           H  
HETATM   14  H3  UNL     1       3.453   0.178  -0.152  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.579   2.612   1.031  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.760   1.811   0.839  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5    5   11
CONECT    5    6   12
CONECT    6    7    7   13
CONECT    7    8    9
CONECT    8   14
CONECT    9   10   11   11
CONECT   10   15
CONECT   11   16
END
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SMILES for NP0002671 (4-Nitrocatechol)

OC1=C(O)C=C(C=C1)[N+]([O-])=O
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INCHI for NP0002671 (4-Nitrocatechol)

InChI=1S/C6H5NO4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H
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View in JSmol
Synonyms
ValueSource
1,2-Dihydroxy-4-nitrobenzeneChEBI
4-NitropyrocatecholChEBI
3,4-Dihydroxy-1-nitrobenzeneHMDB
3,4-DihydroxynitrobenzeneHMDB
4-nitro-1,2-BenzenediolHMDB
4-nitro-1,2-DihydroxybenzeneHMDB
4-nitro-Pyrocatechol4-nitropyrocatechol NSC 80651HMDB
4-NitrobenzcatechinHMDB
P-NitrocatecholHMDB
2-Hydroxy-4-nitrophenolateHMDB
4-Nitro-1,2-benzenediolHMDB
4-Nitro-1,2-dihydroxybenzeneHMDB
4-NitrocatecholHMDB
p-NitrocatecholHMDB
Chemical FormulaC6H5NO4
Average Mass155.1082 Da
Monoisotopic Mass155.02186 Da
IUPAC Name4-nitrobenzene-1,2-diol
Traditional Name4-nitrocatechol
CAS Registry NumberNot Available
SMILES
OC1=C(O)C=C(C=C1)[N+]([O-])=O
InChI Identifier
InChI=1S/C6H5NO4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H
InChI KeyXJNPNXSISMKQEX-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as nitrophenols. Nitrophenols are compounds containing a nitrophenol moiety, which consists of a benzene ring bearing both a hydroxyl group and a nitro group on two different ring carbon atoms.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassNitrophenols
Direct ParentNitrophenols
Alternative Parents
Substituents
  • Nitrophenol
  • Nitrobenzene
  • Nitroaromatic compound
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • C-nitro compound
  • Organic nitro compound
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP1.26ALOGPS
logP1.31ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)7.18ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.34 m³·mol⁻¹ChemAxon
Polarizability13.12 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0002916
DrugBank IDDB03407
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023081
KNApSAcK IDNot Available
Chemspider ID2745027
KEGG Compound IDC02235
BioCyc IDCPD-158
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3505109
PDB IDNot Available
ChEBI ID16318
Good Scents IDNot Available
References
General References
  1. Tassaneeyakul W, Veronese ME, Birkett DJ, Gonzalez FJ, Miners JO: Validation of 4-nitrophenol as an in vitro substrate probe for human liver CYP2E1 using cDNA expression and microsomal kinetic techniques. Biochem Pharmacol. 1993 Dec 3;46(11):1975-81. doi: 10.1016/0006-2952(93)90639-e. [PubMed:8267647 ]
  2. Duescher RJ, Elfarra AA: Determination of p-nitrophenol hydroxylase activity of rat liver microsomes by high-pressure liquid chromatography. Anal Biochem. 1993 Aug 1;212(2):311-4. doi: 10.1006/abio.1993.1335. [PubMed:8214571 ]
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