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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2007-05-22 16:19:02 UTC

Update Date

2023-02-21 17:17:15 UTC

HMDB ID

HMDB0006200

Secondary Accession Numbers

HMDB06200

Metabolite Identification

Common Name

2,4-Dihydroxy-nitrophenol

Description

2,4-Dihydroxy-nitrophenol 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. 2,4-Dihydroxy-nitrophenol 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 2,4-dihydroxy-nitrophenol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2,4-Dihydroxy-nitrophenol.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Nitrobenzene-1,3-diol	HMDB
4-Nitroresorcinol	HMDB

Chemical Formula

C₆H₅NO₄

Average Molecular Weight

155.1082

Monoisotopic Molecular Weight

155.021857653

IUPAC Name

4-nitrobenzene-1,3-diol

Traditional Name

2,4 dihydroxy nitrophenol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

CYEZXDVLBGFROE-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
Resorcinol
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
Organooxygen compound
Organonitrogen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0006200)
Extracellular (HMDB: HMDB0006200)

Source

Endogenous

Endogenous (HMDB: HMDB0006200)

Microbe

Microbe (HMDB: HMDB0006200)

Exogenous

Exogenous (HMDB: HMDB0006200)

Food

Animal origin

Poultry

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)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

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)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	6.99 g/L	ALOGPS
logP	1.5	ALOGPS
logP	1.31	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	6.34	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	86.28 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.34 m³·mol⁻¹	ChemAxon
Polarizability	13.04 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]+	132.858	31661259
DarkChem	[M-H]-	128.504	31661259
DeepCCS	[M+H]+	132.097	30932474
DeepCCS	[M-H]-	128.818	30932474
DeepCCS	[M-2H]-	165.75	30932474
DeepCCS	[M+Na]+	140.749	30932474
AllCCS	[M+H]+	132.0	32859911
AllCCS	[M+H-H2O]+	127.5	32859911
AllCCS	[M+NH4]+	136.2	32859911
AllCCS	[M+Na]+	137.4	32859911
AllCCS	[M-H]-	124.7	32859911
AllCCS	[M+Na-2H]-	125.8	32859911
AllCCS	[M+HCOO]-	127.2	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,4-Dihydroxy-nitrophenol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C([N+](=O)[O-])C(O)=C1	1640.4	Semi standard non polar	33892256
2,4-Dihydroxy-nitrophenol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C([N+](=O)[O-])C(O)=C1	1548.3	Standard non polar	33892256
2,4-Dihydroxy-nitrophenol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C([N+](=O)[O-])C(O)=C1	2149.9	Standard polar	33892256
2,4-Dihydroxy-nitrophenol,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC=C1[N+](=O)[O-]	1640.4	Semi standard non polar	33892256
2,4-Dihydroxy-nitrophenol,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC=C1[N+](=O)[O-]	1592.1	Standard non polar	33892256
2,4-Dihydroxy-nitrophenol,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC=C1[N+](=O)[O-]	2105.8	Standard polar	33892256
2,4-Dihydroxy-nitrophenol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C([N+](=O)[O-])C(O[Si](C)(C)C)=C1	1719.5	Semi standard non polar	33892256
2,4-Dihydroxy-nitrophenol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C([N+](=O)[O-])C(O[Si](C)(C)C)=C1	1633.8	Standard non polar	33892256
2,4-Dihydroxy-nitrophenol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C([N+](=O)[O-])C(O[Si](C)(C)C)=C1	1829.7	Standard polar	33892256
2,4-Dihydroxy-nitrophenol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([N+](=O)[O-])C(O)=C1	1922.2	Semi standard non polar	33892256
2,4-Dihydroxy-nitrophenol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([N+](=O)[O-])C(O)=C1	1771.8	Standard non polar	33892256
2,4-Dihydroxy-nitrophenol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([N+](=O)[O-])C(O)=C1	2239.7	Standard polar	33892256
2,4-Dihydroxy-nitrophenol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC=C1[N+](=O)[O-]	1899.3	Semi standard non polar	33892256
2,4-Dihydroxy-nitrophenol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC=C1[N+](=O)[O-]	1821.4	Standard non polar	33892256
2,4-Dihydroxy-nitrophenol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC=C1[N+](=O)[O-]	2213.6	Standard polar	33892256
2,4-Dihydroxy-nitrophenol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([N+](=O)[O-])C(O[Si](C)(C)C(C)(C)C)=C1	2196.4	Semi standard non polar	33892256
2,4-Dihydroxy-nitrophenol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([N+](=O)[O-])C(O[Si](C)(C)C(C)(C)C)=C1	2095.7	Standard non polar	33892256
2,4-Dihydroxy-nitrophenol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C([N+](=O)[O-])C(O[Si](C)(C)C(C)(C)C)=C1	2083.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Dihydroxy-nitrophenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-8900000000-f5a16ea875eb9654f794	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Dihydroxy-nitrophenol GC-MS (2 TMS) - 70eV, Positive	splash10-00di-9380000000-543e33ea82177ad250b6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,4-Dihydroxy-nitrophenol 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-nitrophenol 10V, Positive-QTOF	splash10-0a4i-0900000000-c678e5e84c3f4cff2d7a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-nitrophenol 20V, Positive-QTOF	splash10-052r-0900000000-90078fc2118fd684fe9d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-nitrophenol 40V, Positive-QTOF	splash10-03di-5900000000-3760770db292d120978d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-nitrophenol 10V, Negative-QTOF	splash10-0udi-0900000000-7e507d25285932920903	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-nitrophenol 20V, Negative-QTOF	splash10-0udi-0900000000-868333d382b2e6c6890f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-nitrophenol 40V, Negative-QTOF	splash10-0w2c-4900000000-a123d9bd989cafa7594f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-nitrophenol 10V, Positive-QTOF	splash10-0a4i-0900000000-ec0e93e84874e2f3187f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-nitrophenol 20V, Positive-QTOF	splash10-0a4i-0900000000-612c6ab5ffa3d7fa282f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-nitrophenol 40V, Positive-QTOF	splash10-0hfx-9100000000-7f08c8c5021c1b7b603d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-nitrophenol 10V, Negative-QTOF	splash10-0udi-0900000000-c23d0f4048cedb728ea2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-nitrophenol 20V, Negative-QTOF	splash10-0udi-2900000000-7e94590ff2e781b7dcdb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,4-Dihydroxy-nitrophenol 40V, Negative-QTOF	splash10-0006-9000000000-a3e3c31562c05b256507	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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

Cytoplasm
Extracellular

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023833

KNApSAcK ID

Not Available

Chemspider ID

69087

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2300001

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76623

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 2,4-Dihydroxy-nitrophenol (HMDB0006200)

MOL for HMDB0006200 (2,4-Dihydroxy-nitrophenol)

3D MOL for HMDB0006200 (2,4-Dihydroxy-nitrophenol)

3D SDF for HMDB0006200 (2,4-Dihydroxy-nitrophenol)

3D-SDF for HMDB0006200 (2,4-Dihydroxy-nitrophenol)

PDB for HMDB0006200 (2,4-Dihydroxy-nitrophenol)

3D PDB for HMDB0006200 (2,4-Dihydroxy-nitrophenol)

SMILES for HMDB0006200 (2,4-Dihydroxy-nitrophenol)

INCHI for HMDB0006200 (2,4-Dihydroxy-nitrophenol)

Structure for HMDB0006200 (2,4-Dihydroxy-nitrophenol)

3D Structure for HMDB0006200 (2,4-Dihydroxy-nitrophenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra