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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:34:09 UTC

Update Date

2021-09-26 22:54:00 UTC

HMDB ID

HMDB0245504

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,5-Dinitrophenol

Description

2,5-Dinitrophenol, also known as 2,5-DNP or gamma-dinitrophenol, belongs to the class of organic compounds known as dinitrophenols. These are organic aromatic compounds containing a benzene that carries a single phenol group and exactly two nitro groups. Based on a literature review very few articles have been published on 2,5-Dinitrophenol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,5-dinitrophenol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,5-Dinitrophenol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   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   0.000   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    5                                                       
CONECT    3    4    6                                                       
CONECT    4    1    3    7                                                  
CONECT    5    2    6    8                                                  
CONECT    6    3    5    9                                                  
CONECT    7    4   10   11                                                  
CONECT    8    5   12   13                                                  
CONECT    9    6                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    8                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,5-DNP	ChEBI
gamma-Dinitrophenol	ChEBI
g-Dinitrophenol	Generator
Γ-dinitrophenol	Generator
2,5-Dinitrophenol, sodium salt	HMDB

Chemical Formula

C₆H₄N₂O₅

Average Molecular Weight

184.1064

Monoisotopic Molecular Weight

184.012021248

IUPAC Name

2,5-dinitrophenol

Traditional Name

2,5-dinitrophenol

CAS Registry Number

Not Available

SMILES

OC1=C(C=CC(=C1)N(=O)=O)N(=O)=O

InChI Identifier

InChI=1S/C6H4N2O5/c9-6-3-4(7(10)11)1-2-5(6)8(12)13/h1-3,9H

InChI Key

UWEZBKLLMKVIPI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dinitrophenols. These are organic aromatic compounds containing a benzene that carries a single phenol group and exactly two nitro groups.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Dinitrophenol
Nitrobenzene
Nitroaromatic compound
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
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

dinitrophenol (CHEBI:40810 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	1.9	ALOGPS
logP	1.55	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	5.21	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.87 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.69 m³·mol⁻¹	ChemAxon
Polarizability	14.5 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
DeepCCS	[M+H]+	132.848	30932474
DeepCCS	[M-H]-	130.453	30932474
DeepCCS	[M-2H]-	165.771	30932474
DeepCCS	[M+Na]+	141.002	30932474
AllCCS	[M+H]+	136.6	32859911
AllCCS	[M+H-H2O]+	132.3	32859911
AllCCS	[M+NH4]+	140.5	32859911
AllCCS	[M+Na]+	141.6	32859911
AllCCS	[M-H]-	129.4	32859911
AllCCS	[M+Na-2H]-	129.9	32859911
AllCCS	[M+HCOO]-	130.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,5-Dinitrophenol	OC1=C(C=CC(=C1)N(=O)=O)N(=O)=O	2574.4	Standard polar	33892256
2,5-Dinitrophenol	OC1=C(C=CC(=C1)N(=O)=O)N(=O)=O	1467.3	Standard non polar	33892256
2,5-Dinitrophenol	OC1=C(C=CC(=C1)N(=O)=O)N(=O)=O	1489.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dinitrophenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-5900000000-254744febfdfb2129c4e	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dinitrophenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dinitrophenol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5-Dinitrophenol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	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 - 2,5-Dinitrophenol 10V, Positive-QTOF	splash10-000i-0900000000-9b01c6dbcc3563f7c31c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dinitrophenol 20V, Positive-QTOF	splash10-0a6r-0900000000-66cce0f03d8f9887a78d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dinitrophenol 40V, Positive-QTOF	splash10-056s-1900000000-f6c6328e672ca04c7bdc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dinitrophenol 10V, Negative-QTOF	splash10-001i-0900000000-d71aa45058bf36dd2145	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dinitrophenol 20V, Negative-QTOF	splash10-001i-0900000000-b71b201ac9947a4cbfd9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5-Dinitrophenol 40V, Negative-QTOF	splash10-0059-2900000000-2e54d2868c5ad48e4168	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9120

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9492

PDB ID

Not Available

ChEBI ID

40810

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 2,5-Dinitrophenol (HMDB0245504)

MOL for HMDB0245504 (2,5-Dinitrophenol)

3D MOL for HMDB0245504 (2,5-Dinitrophenol)

3D SDF for HMDB0245504 (2,5-Dinitrophenol)

3D-SDF for HMDB0245504 (2,5-Dinitrophenol)

PDB for HMDB0245504 (2,5-Dinitrophenol)

3D PDB for HMDB0245504 (2,5-Dinitrophenol)

SMILES for HMDB0245504 (2,5-Dinitrophenol)

INCHI for HMDB0245504 (2,5-Dinitrophenol)

Structure for HMDB0245504 (2,5-Dinitrophenol)

3D Structure for HMDB0245504 (2,5-Dinitrophenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra