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Showing metabocard for 4-Nitrophenol (HMDB0001232)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:32 UTC
HMDB IDHMDB0001232
Secondary Accession Numbers
  • HMDB0062627
  • HMDB01232
  • HMDB62627
Metabolite 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 HMDB0001232 (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
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3D MOL for HMDB0001232 (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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3D SDF for HMDB0001232 (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>
HMDB0001232

> <DATABASE_NAME>
hmdb

> <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

$$$$
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3D-SDF for HMDB0001232 (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 HMDB0001232 (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 HMDB0001232 (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 HMDB0001232 (4-Nitrophenol)

OC1=CC=C(C=C1)[N+]([O-])=O
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INCHI for HMDB0001232 (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 JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC6H5NO3
Average Molecular Weight139.1088
Monoisotopic Molecular Weight139.026943031
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
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
Ontology
Physiological effectNot Available
Disposition
Source
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point113.8 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility11.6 mg/mLNot Available
LogP1.91HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Intestine
  • Liver
  • Placenta
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
 details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04417
Phenol Explorer Compound IDNot Available
FooDB IDFDB022503
KNApSAcK IDNot Available
Chemspider ID955
KEGG Compound IDC00870
BioCyc IDP-NITROPHENOL
BiGG ID36247
Wikipedia Link4-Nitrophenol
METLIN ID4100
PubChem Compound980
PDB IDNot Available
ChEBI ID16836
Food Biomarker OntologyNot Available
VMH ID4NPH
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceFache, Eric; Righini, Sebastien. Preparation of a nitrophenol. Fr. Demande (2004), 35 pp.
Material Safety Data Sheet (MSDS)Not Available
General References

Only showing the first 10 proteins. There are 13 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details
1. Serum paraoxonase/lactonase 3
General function:
Involved in arylesterase activity
Specific function:
Has low activity towards the organophosphate paraxon and aromatic carboxylic acid esters. Rapidly hydrolyzes lactones such as statin prodrugs (e.g. lovastatin). Hydrolyzes aromatic lactones and 5- or 6-member ring lactones with aliphatic substituents but not simple lactones or those with polar substituents.
Gene Name:
PON3
Uniprot ID:
Q15166
Molecular weight:
39607.185
Reactions
Parathion + Water → Diethylthiophosphate + 4-Nitrophenoldetails
Paraoxon + Water → Diethylphosphate + 4-Nitrophenoldetails
Enzyme Details
2. Alkaline phosphatase, placental type
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPP
Uniprot ID:
P05187
Molecular weight:
57953.31
Reactions
4-Nitrophenyl phosphate + Water → 4-Nitrophenol + Phosphatedetails
Enzyme Details
3. Serum paraoxonase/arylesterase 1
General function:
Involved in arylesterase activity
Specific function:
Hydrolyzes the toxic metabolites of a variety of organophosphorus insecticides. Capable of hydrolyzing a broad spectrum of organophosphate substrates and lactones, and a number of aromatic carboxylic acid esters. Mediates an enzymatic protection of low density lipoproteins against oxidative modification and the consequent series of events leading to atheroma formation.
Gene Name:
PON1
Uniprot ID:
P27169
Molecular weight:
39730.99
Reactions
Parathion + Water → Diethylthiophosphate + 4-Nitrophenoldetails
Paraoxon + Water → Diethylphosphate + 4-Nitrophenoldetails
Enzyme Details
4. Serum paraoxonase/arylesterase 2
General function:
Involved in arylesterase activity
Specific function:
Capable of hydrolyzing lactones and a number of aromatic carboxylic acid esters. Has antioxidant activity. Is not associated with high density lipoprotein. Prevents LDL lipid peroxidation, reverses the oxidation of mildly oxidized LDL, and inhibits the ability of MM-LDL to induce monocyte chemotaxis.
Gene Name:
PON2
Uniprot ID:
Q15165
Molecular weight:
39380.535
Reactions
Parathion + Water → Diethylthiophosphate + 4-Nitrophenoldetails
Paraoxon + Water → Diethylphosphate + 4-Nitrophenoldetails
Enzyme Details
5. Intestinal-type alkaline phosphatase
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPI
Uniprot ID:
P09923
Molecular weight:
56811.695
Reactions
4-Nitrophenyl phosphate + Water → 4-Nitrophenol + Phosphatedetails
Enzyme Details
6. Alkaline phosphatase, tissue-nonspecific isozyme
General function:
Involved in catalytic activity
Specific function:
This isozyme may play a role in skeletal mineralization.
Gene Name:
ALPL
Uniprot ID:
P05186
Molecular weight:
57304.435
Reactions
4-Nitrophenyl phosphate + Water → 4-Nitrophenol + Phosphatedetails
Enzyme Details
7. Tartrate-resistant acid phosphatase type 5
General function:
Involved in hydrolase activity
Specific function:
Involved in osteopontin/bone sialoprotein dephosphorylation. Its expression seems to increase in certain pathological states such as Gaucher and Hodgkin diseases, the hairy cell, the B-cell, and the T-cell leukemias.
Gene Name:
ACP5
Uniprot ID:
P13686
Molecular weight:
36598.47
Enzyme Details
8. Prostatic acid phosphatase
General function:
Involved in acid phosphatase activity
Specific function:
A non-specific tyrosine phosphatase that dephosphorylates a diverse number of substrates under acidic conditions (pH 4-6) including alkyl, aryl, and acyl orthophosphate monoesters and phosphorylated proteins. Has lipid phosphatase activity and inactivates lysophosphatidic acid in seminal plasma. Isoform 2: the cellular form also has ecto-5'-nucleotidase activity in dorsal root ganglion (DRG) neurons. Generates adenosine from AMP which acts as a pain suppressor. Acts as a tumor suppressor of prostate cancer through dephosphorylation of ERBB2 and deactivation of MAPK-mediated signaling.
Gene Name:
ACPP
Uniprot ID:
P15309
Molecular weight:
44565.715
Enzyme Details
9. Alkaline phosphatase, placental-like
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ALPPL2
Uniprot ID:
P10696
Molecular weight:
57376.515
Reactions
4-Nitrophenyl phosphate + Water → 4-Nitrophenol + Phosphatedetails
Enzyme Details
10. Cytochrome P450 2E1
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
Reactions
4-Nitrophenol + NADPH + Oxygen → 4-Nitrocatechol + NADP + Waterdetails

Only showing the first 10 proteins. There are 13 proteins in total.

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