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Showing NP-Card for p-Nitrophenol (NP0331700)

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Record Information
Version1.0
Created at2023-06-27 20:00:20 UTC
Updated at2024-04-19 09:48:53 UTC
NP-MRD IDNP0331700
Secondary Accession NumbersNone
Natural Product Identification
Common Namep-Nitrophenol
Description4-Nitrophenol, also known as niphen or PNP, 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 exists in all living species, ranging from bacteria to plants to humans. 4-Nitrophenol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. It was first documented in 2021 (PMID: 34598165). Based on a literature review a significant number of articles have been published on 4-Nitrophenol (PMID: 34589566) (PMID: 34585791) (PMID: 34577151) (PMID: 34562739) (PMID: 34559304) (PMID: 34550140).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0331700 (p-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 NP0331700 (p-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 NP0331700 (p-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>
NP0331700

> <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 NP0331700 (p-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

PDB for NP0331700 (p-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 NP0331700 (p-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 NP0331700 (p-Nitrophenol)

OC1=CC=C(C=C1)[N+]([O-])=O
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INCHI for NP0331700 (p-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 NumberNot Available
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 NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2023-06-27View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)ztmnb@umsystem.eduNot AvailableNot Available2023-06-27View Spectrum
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
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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. Mundekkad D, Kameshwari GV, Karchalkar P, Koti R: The catalytic and ROS-scavenging activities of green synthesized, antiferromagneticalpha-Fe(2)O(3)nanoparticle with a prismatic octahedron morphology from pomegranate rind extract. Nanotechnology. 2021 Nov 5;33(4). doi: 10.1088/1361-6528/ac2c45. [PubMed:34598165 ]
  2. Arora PK, Saroj RS, Mishra R, Omar RA, Kumari P, Srivastava A, Garg SK, Singh VP: Draft genome sequence data of a 4-nitrophenol- degrading bacterium, Pseudomonas alloputida strain PNP. Data Brief. 2021 Sep 20;38:107390. doi: 10.1016/j.dib.2021.107390. eCollection 2021 Oct. [PubMed:34589566 ]
  3. Kostelenos K, Bairamis F, Karamoschos N, Sygellou L, Andrikopoulos KS, Konstantinou I, Tasis D: Highly Efficient Simulated Solar Light-Driven Photocatalytic Degradation of 4-Nitrophenol over CdS/Carbon/MoS(x) Hybrids. Chemistry. 2021 Nov 11;27(63):15806-15814. doi: 10.1002/chem.202103008. Epub 2021 Oct 11. [PubMed:34585791 ]
  4. Krebsz M, Kotai L, Sajo IE, Vaczi T, Pasinszki T: Carbon Microsphere-Supported Metallic Nickel Nanoparticles as Novel Heterogeneous Catalysts and Their Application for the Reduction of Nitrophenol. Molecules. 2021 Sep 18;26(18):5680. doi: 10.3390/molecules26185680. [PubMed:34577151 ]
  5. Su X, Jonnalagadda US, Bharatula LD, Kwan JJ: Unsupported gold nanocones as sonocatalytic agents with enhanced catalytic properties. Ultrason Sonochem. 2021 Nov;79:105753. doi: 10.1016/j.ultsonch.2021.105753. Epub 2021 Sep 13. [PubMed:34562739 ]
  6. Harby AG, El-Borady OM, El-Kemary M: The exploitation of rice husk biomass for the bio-inspired synthesis of gold nanoparticles as a multifunctional material for various biological and photocatalytic applications. Bioprocess Biosyst Eng. 2022 Jan;45(1):61-74. doi: 10.1007/s00449-021-02639-y. Epub 2021 Sep 24. [PubMed:34559304 ]
  7. Prasanna, Usha KM, Hegde MS: Highly recyclable Ti(0.97)Ni(0.03)O(1.97) catalyst coated on cordierite monolith for efficient transformation of arylboronic acids to phenols and reduction of 4-nitrophenol. Dalton Trans. 2021 Oct 19;50(40):14223-14234. doi: 10.1039/d1dt02293h. [PubMed:34550140 ]
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