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Showing NP-Card for 4-Nitrophenol (NP0000780)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:40:12 UTC
NP-MRD IDNP0000780
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Nitrophenol
Description4-Nitrophenol (also called p-nitrophenol or 4-hydroxynitrobenzene) is a phenolic compound that has a nitro group at the opposite position of the hydroxyl group on the benzene ring. It 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-Nitrophenol shows two polymorphs in the crystalline state. The alpha-form is colorless pillars, unstable at room temperature, and stable toward sunlight. The beta-form is yellow pillars, stable at room temperature, and gradually turns red upon irradiation of sunlight. Usually 4-nitrophenol exists as a mixture of these two forms. 4-Nitrophenol can be used as a pH indicator and as an intermediate in the synthesis of paracetamol. Itis also used as the precursor for the preparation of phenetidine and acetophenetidine, indicators, and raw materials for fungicides. Bioaccumulation of this compound rarely occurs. In peptide synthesis, carboxylate ester derivatives of 4-nitrophenol may serve as activated components for construction of amide moieties. 4-Nitrophenol is a potentially toxic compound: It can cause eyes, skin, and respiratory tract irritations. It may also cause inflammation of those parts. It has a delayed interaction with blood and forms methaemoglobin which is responsible for methemoglobinemia -which is characterized by tissue hypoxia, as methemoglobin cannot bind oxygen-, potentially causing cyanosis, confusion, and unconsciousness. When ingested, it causes abdominal pain and vomiting. Prolonged contact with skin may cause allergic response. Genotoxicity and carcinogenicity of 4-nitrophenol are not known. The LD50 in mice is 282 mg/kg and in rats is 202 mg/kg. Outside of the human body, 4-Nitrophenol has been detected, but not quantified in cow milk. Conjugates are more polar than the parent compounds and therefore are easier to excrete in the urine.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000780 (4-Nitrophenol)


  Mrv1652305261923592D          

 10 10  0  0  0  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  6  1  1  0  0  0  0
 10  1  1  0  0  0  0
M  CHG  2   7   1   8  -1
M  END
Download

3D MOL for NP0000780 (4-Nitrophenol)

HMDB0001232
     RDKit          3D
4-Nitrophenol
 15 15  0  0  0  0  0  0  0  0999 V2000
    3.2789   -0.7586    0.3372 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5719    0.2549    0.1942 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.1968    1.4756    0.1787 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.1619    0.1161    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3320    1.2058   -0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0379    1.0599   -0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6367   -0.1822   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0238   -0.3278   -0.3607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8128   -1.2766   -0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5517   -1.1211    0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7868    2.1881   -0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7061    1.9116   -0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5846   -0.3155    0.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2787   -2.2545   -0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2006   -1.9757    0.1982 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  2  0
 10  4  1  0
  5 11  1  0
  6 12  1  0
  8 13  1  0
  9 14  1  0
 10 15  1  0
M  CHG  2   2   1   3  -1
M  END
Download

3D SDF for NP0000780 (4-Nitrophenol)


  Mrv1652305261923592D          

 10 10  0  0  0  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  6  1  1  0  0  0  0
 10  1  1  0  0  0  0
M  CHG  2   7   1   8  -1
M  END
> <DATABASE_ID>
NP0000780

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H

> <INCHI_KEY>
BTJIUGUIPKRLHP-UHFFFAOYSA-N

> <FORMULA>
C6H5NO3

> <MOLECULAR_WEIGHT>
139.1088

> <EXACT_MASS>
139.026943031

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
12.22225146272029

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-nitrophenol

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
1.6096646836666664

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.0749669885710444

> <JCHEM_PKA_STRONGEST_BASIC>
-7.134669899557051

> <JCHEM_POLAR_SURFACE_AREA>
63.37

> <JCHEM_REFRACTIVITY>
34.3594

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.60e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
P-nitrophenol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000780 (4-Nitrophenol)

HMDB0001232
     RDKit          3D
4-Nitrophenol
 15 15  0  0  0  0  0  0  0  0999 V2000
    3.2789   -0.7586    0.3372 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5719    0.2549    0.1942 N   0  0  0  0  0  4  0  0  0  0  0  0
    3.1968    1.4756    0.1787 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.1619    0.1161    0.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3320    1.2058   -0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0379    1.0599   -0.2429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6367   -0.1822   -0.2232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0238   -0.3278   -0.3607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8128   -1.2766   -0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5517   -1.1211    0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7868    2.1881   -0.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7061    1.9116   -0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5846   -0.3155    0.5044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2787   -2.2545   -0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2006   -1.9757    0.1982 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  2  0
 10  4  1  0
  5 11  1  0
  6 12  1  0
  8 13  1  0
  9 14  1  0
 10 15  1  0
M  CHG  2   2   1   3  -1
M  END
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PDB for NP0000780 (4-Nitrophenol)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+1
HETATM    8  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O-1
HETATM    9  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    6   10                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    1                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for NP0000780 (4-Nitrophenol)

COMPND    HMDB0001232
HETATM    1  O1  UNL     1       3.279  -0.759   0.337  1.00  0.00           O  
HETATM    2  N1  UNL     1       2.572   0.255   0.194  1.00  0.00           N1+
HETATM    3  O2  UNL     1       3.197   1.476   0.179  1.00  0.00           O1-
HETATM    4  C1  UNL     1       1.162   0.116   0.054  1.00  0.00           C  
HETATM    5  C2  UNL     1       0.332   1.206  -0.107  1.00  0.00           C  
HETATM    6  C3  UNL     1      -1.038   1.060  -0.243  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.637  -0.182  -0.223  1.00  0.00           C  
HETATM    8  O3  UNL     1      -3.024  -0.328  -0.361  1.00  0.00           O  
HETATM    9  C5  UNL     1      -0.813  -1.277  -0.062  1.00  0.00           C  
HETATM   10  C6  UNL     1       0.552  -1.121   0.072  1.00  0.00           C  
HETATM   11  H1  UNL     1       0.787   2.188  -0.125  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.706   1.912  -0.371  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.585  -0.315   0.504  1.00  0.00           H  
HETATM   14  H4  UNL     1      -1.279  -2.255  -0.046  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.201  -1.976   0.198  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5    5   10
CONECT    5    6   11
CONECT    6    7    7   12
CONECT    7    8    9
CONECT    8   13
CONECT    9   10   10   14
CONECT   10   15
END
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SMILES for NP0000780 (4-Nitrophenol)

OC1=CC=C(C=C1)[N+]([O-])=O
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INCHI for NP0000780 (4-Nitrophenol)

InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H
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View in JSmol
Synonyms
ValueSource
4-HydroxynitrobenzeneChEBI
NiphenChEBI
p-HydroxynitrobenzeneChEBI
p-NitrophenolChEBI
ParanitrophenolChEBI
PNPChEBI
MononitrophenolHMDB
1-Hydroxy-4-nitrobenzeneHMDB
4-Nitrophenol, (18)O-labeled CPDHMDB
4-Nitrophenol, 1-(13)C-labeled CPDHMDB
4-Nitrophenol, manganese (2+) saltHMDB
4-Nitrophenol, silver(2+) saltHMDB
4-Nitrophenol, sodium salt, (2:1), dihydrateHMDB
4-Nitrophenol, tin (4+) saltHMDB
4-Nitrophenol, 2,6-(13)C2-labeled CPDHMDB
4-Nitrophenol, 2-(14)C-labeled CPDHMDB
4-Nitrophenol, copper(1+) saltHMDB
4-Nitrophenol, potassium saltHMDB
4-Nitrophenol, tin (2+) saltHMDB
4-Nitrophenol, 14C-labeled CPDHMDB
4-Nitrophenol, ammonium saltHMDB
4-Nitrophenol, ion(1-)HMDB
4-Nitrophenol, ion(1-) hydrideHMDB
4-Nitrophenol, sodium saltHMDB
4-Nitrophenol, 2,6-(14)C2-labeled CPDHMDB
4-Nitrophenol, aluminum saltHMDB
4-Nitrophenol, cesium saltHMDB
4-Nitrophenol, iron(3+) saltHMDB
4-Nitrophenol, lithium saltHMDB
4-Nitrophenol, manganese saltHMDB
4-Nitrophenol, zinc saltHMDB
4-Hydroxy-1-nitrobenzeneHMDB
4-NitrophenolateHMDB
4-NitrophenolHMDB
Chemical FormulaC6H5NO3
Average Mass139.1088 Da
Monoisotopic Mass139.02694 Da
IUPAC Name4-nitrophenol
Traditional NameP-nitrophenol
CAS Registry Number100-02-7
SMILES
OC1=CC=C(C=C1)[N+]([O-])=O
InChI Identifier
InChI=1S/C6H5NO3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H
InChI KeyBTJIUGUIPKRLHP-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
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
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
Vitis viniferaLOTUS Database
Species Where Detected
Species NameSourceReference
Monascus purpureus BCRC 38113KNApSAcK Database
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
  • 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
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point113.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.6 mg/mLNot Available
LogP1.91Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility3.6 g/LALOGPS
logP1.93ALOGPS
logP1.61ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)7.07ChemAxon
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.37 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.36 m³·mol⁻¹ChemAxon
Polarizability12.22 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001232
DrugBank IDDB04417
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022503
KNApSAcK IDC00056786
Chemspider ID955
KEGG Compound IDC00870
BioCyc IDP-NITROPHENOL
BiGG ID36247
Wikipedia Link4-Nitrophenol
METLIN ID4100
PubChem Compound980
PDB IDNot Available
ChEBI ID16836
Good Scents IDNot Available
References
General References
  1. Ozawa S, Shimizu M, Katoh T, Miyajima A, Ohno Y, Matsumoto Y, Fukuoka M, Tang YM, Lang NP, Kadlubar FF: Sulfating-activity and stability of cDNA-expressed allozymes of human phenol sulfotransferase, ST1A3*1 ((213)Arg) and ST1A3*2 ((213)His), both of which exist in Japanese as well as Caucasians. J Biochem. 1999 Aug;126(2):271-7. [PubMed:10423517 ]
  2. Sharaev PN, Gabdrakhmanova NK, Strelkova TN, Sakhabutdinova EP: [Detection of N-acetyl-beta-D-hexosaminidase in urine]. Klin Lab Diagn. 2004 May;(5):40-2. [PubMed:15230116 ]
  3. Anderson RJ, Garcia MJ, Liebentritt DK, Kay HD: Localization of human blood phenol sulfotransferase activities: novel detection of the thermostable enzyme in granulocytes. J Lab Clin Med. 1991 Nov;118(5):500-9. [PubMed:1940590 ]
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