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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 15:12:19 UTC

Update Date

2023-02-21 17:16:29 UTC

HMDB ID

HMDB0002916

Secondary Accession Numbers

HMDB0062694
HMDB02916
HMDB62694

Metabolite Identification

Common Name

4-Nitrocatechol

Description

4-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 has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 4-nitrocatechol a potential biomarker for the consumption of these foods. 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. Based on a literature review a significant number of articles have been published on 4-Nitrocatechol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2-Dihydroxy-4-nitrobenzene	ChEBI
4-Nitropyrocatechol	ChEBI
3,4-Dihydroxy-1-nitrobenzene	HMDB
3,4-Dihydroxynitrobenzene	HMDB
4-nitro-1,2-Benzenediol	HMDB
4-nitro-1,2-Dihydroxybenzene	HMDB
4-nitro-Pyrocatechol4-nitropyrocatechol NSC 80651	HMDB
4-Nitrobenzcatechin	HMDB
P-Nitrocatechol	HMDB
2-Hydroxy-4-nitrophenolate	HMDB
4-Nitro-1,2-benzenediol	HMDB
4-Nitro-1,2-dihydroxybenzene	HMDB
4-Nitrocatechol	HMDB
p-Nitrocatechol	HMDB

Chemical Formula

C₆H₅NO₄

Average Molecular Weight

155.1082

Monoisotopic Molecular Weight

155.021857653

IUPAC Name

4-nitrobenzene-1,2-diol

Traditional Name

4-nitrocatechol

CAS Registry Number

3316-09-4

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

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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

C-nitro compound (CHEBI:16318 )
catechols (CHEBI:16318 )
a catechol (CPD-158 )
a nitroaromatic compound (CPD-158 )

Ontology

Not Available

Endogenous (HMDB: HMDB0002916)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0002916)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	174 - 176 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	1.66	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	7.76 g/L	ALOGPS
logP	1.26	ALOGPS
logP	1.31	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	7.18	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	36.34 m³·mol⁻¹	ChemAxon
Polarizability	13.12 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	132.781	31661259
DarkChem	[M-H]-	129.84	31661259
DeepCCS	[M+H]+	131.953	30932474
DeepCCS	[M-H]-	128.65	30932474
DeepCCS	[M-2H]-	165.6	30932474
DeepCCS	[M+Na]+	140.603	30932474
AllCCS	[M+H]+	132.3	32859911
AllCCS	[M+H-H2O]+	127.8	32859911
AllCCS	[M+NH4]+	136.5	32859911
AllCCS	[M+Na]+	137.7	32859911
AllCCS	[M-H]-	125.2	32859911
AllCCS	[M+Na-2H]-	126.4	32859911
AllCCS	[M+HCOO]-	127.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Nitrocatechol	OC1=C(O)C=C(C=C1)[N+]([O-])=O	3237.3	Standard polar	33892256
4-Nitrocatechol	OC1=C(O)C=C(C=C1)[N+]([O-])=O	1529.4	Standard non polar	33892256
4-Nitrocatechol	OC1=C(O)C=C(C=C1)[N+]([O-])=O	1742.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Nitrocatechol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C([N+](=O)[O-])C=C1O	1654.4	Semi standard non polar	33892256
4-Nitrocatechol,1TMS,isomer #2	C[Si](C)(C)OC1=CC([N+](=O)[O-])=CC=C1O	1594.0	Semi standard non polar	33892256
4-Nitrocatechol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C([N+](=O)[O-])C=C1O[Si](C)(C)C	1687.5	Semi standard non polar	33892256
4-Nitrocatechol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([N+](=O)[O-])C=C1O	1940.2	Semi standard non polar	33892256
4-Nitrocatechol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC([N+](=O)[O-])=CC=C1O	1854.3	Semi standard non polar	33892256
4-Nitrocatechol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([N+](=O)[O-])C=C1O[Si](C)(C)C(C)(C)C	2197.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-Nitrocatechol GC-EI-TOF (Non-derivatized)	splash10-001s-1950000000-faaf15fd1ec113f2b54e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Nitrocatechol GC-EI-TOF (Non-derivatized)	splash10-001s-1950000000-faaf15fd1ec113f2b54e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Nitrocatechol GC-EI-TOF (Non-derivatized)	splash10-001s-1950000000-faaf15fd1ec113f2b54e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Nitrocatechol GC-EI-TOF (Non-derivatized)	splash10-001s-1950000000-faaf15fd1ec113f2b54e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrocatechol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4900000000-02b39e2d157c3829375f	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrocatechol GC-MS (2 TMS) - 70eV, Positive	splash10-00di-8390000000-9ce3af1465a211c62c08	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrocatechol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Nitrocatechol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Nitrocatechol 35V, Negative-QTOF	splash10-0fk9-1900000000-20992826e1c86b042245	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nitrocatechol 10V, Positive-QTOF	splash10-0a4i-0900000000-cf479fcf220611c7c282	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nitrocatechol 20V, Positive-QTOF	splash10-0002-0900000000-a438cfc44009c80ae2b1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nitrocatechol 40V, Positive-QTOF	splash10-0f92-3900000000-6a688f91418ed25d4aad	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nitrocatechol 10V, Negative-QTOF	splash10-0udi-0900000000-3a1438af5cfdd1a76453	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nitrocatechol 20V, Negative-QTOF	splash10-0udi-0900000000-64163bd65bd38adfb2cf	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nitrocatechol 40V, Negative-QTOF	splash10-0udl-3900000000-f9fb9e7b1ada6519c087	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nitrocatechol 10V, Positive-QTOF	splash10-0a4i-0900000000-dd65e28b5507a1abfb0e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nitrocatechol 20V, Positive-QTOF	splash10-0a4i-2900000000-ff3f84d5fc5d45d608e5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nitrocatechol 40V, Positive-QTOF	splash10-0udi-9000000000-db86a62064c6c13c1639	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nitrocatechol 10V, Negative-QTOF	splash10-0udi-0900000000-c23d0f4048cedb728ea2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nitrocatechol 20V, Negative-QTOF	splash10-0udi-2900000000-0a7ee2badf00f8f5f00e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Nitrocatechol 40V, Negative-QTOF	splash10-0002-9000000000-a0441e6336543cb88423	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB03407

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023081

KNApSAcK ID

Not Available

Chemspider ID

2745027

KEGG Compound ID

C02235

BioCyc ID

CPD-158

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3505109

PDB ID

Not Available

ChEBI ID

16318

Food Biomarker Ontology

Not Available

VMH ID

24NPH

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [PubMed:8267647 ]
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. [PubMed:8214571 ]

Enzymes

Enzyme Details

1. 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 + Water	details

Showing metabocard for 4-Nitrocatechol (HMDB0002916)

MOL for HMDB0002916 (4-Nitrocatechol)

3D MOL for HMDB0002916 (4-Nitrocatechol)

3D SDF for HMDB0002916 (4-Nitrocatechol)

3D-SDF for HMDB0002916 (4-Nitrocatechol)

PDB for HMDB0002916 (4-Nitrocatechol)

3D PDB for HMDB0002916 (4-Nitrocatechol)

SMILES for HMDB0002916 (4-Nitrocatechol)

INCHI for HMDB0002916 (4-Nitrocatechol)

Structure for HMDB0002916 (4-Nitrocatechol)

3D Structure for HMDB0002916 (4-Nitrocatechol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions