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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2017-03-21 06:14:48 UTC

Update Date

2023-02-21 17:30:52 UTC

HMDB ID

HMDB0062403

Secondary Accession Numbers

HMDB62403

Metabolite Identification

Common Name

4-hydroxy-3-nitrophenylacetate

Description

4-hydroxy-3-nitrophenylacetate, also known as 3-nitro-4-hydroxyphenylacetic acid, is slightly soluble (in water). It is a mildly acidic compound. This metabolite is a member of the class of 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. Free nitrotyrosine undergoes metabolism to form 3-nitro-4-hydroxyphenylacetic acid (NHPA) which is excreted in the urine (Wikipedia). However, it is not known whether NHPA is derived exclusively from metabolism of nitrotyrosine, or whether it can be formed by nitration of circulating para -hydroxyphenylacetic acid (PHPA), a metabolite of tyrosine (PMID: 12797864 ). Since the plasma concentration of PHPA is markedly higher than free nitrotyrosine (approx. 400-fold), the nitration of high-circulating endogenous PHPA to form NHPA becomes very significant and accounts for the majority of NHPA excreted in urine (PMID: 12797864 ).

Structure

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

  Mrv1652305171803112D          

 14 14  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
    2.1434   -0.4125    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 10  5  1  0  0  0  0
 14  8  1  0  0  0  0
M  CHG  2  11   1  12  -1
M  END
> <DATABASE_ID>
HMDB0062403

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CC1=CC(=C(O)C=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H7NO5/c10-7-2-1-5(4-8(11)12)3-6(7)9(13)14/h1-3,10H,4H2,(H,11,12)

> <INCHI_KEY>
QBHBHOSRLDPIHG-UHFFFAOYSA-N

> <FORMULA>
C8H7NO5

> <MOLECULAR_WEIGHT>
197.1449

> <EXACT_MASS>
197.032422339

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
17.100612415475975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-hydroxy-3-nitrophenyl)acetic acid

> <ALOGPS_LOGP>
2.01

> <JCHEM_LOGP>
1.2474129729999999

> <ALOGPS_LOGS>
-2.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.602306026638564

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0188807984153976

> <JCHEM_PKA_STRONGEST_BASIC>
-6.879134626471463

> <JCHEM_POLAR_SURFACE_AREA>
100.67

> <JCHEM_REFRACTIVITY>
45.667

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4-hydroxy-3-nitrophenyl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-MAY-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-MAY-18         0                                  
HETATM    1  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       4.001  -0.770   0.000  0.00  0.00           N+1
HETATM   12  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O-1
HETATM   13  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9    5                                                       
CONECT   11    7   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(4-HYDROXY-3-nitrophenyl)acetIC ACID	ChEBI
4-Hydroxy-3-nitrophenylacetic acid	ChEBI
NO2hpa	ChEBI
2-(4-HYDROXY-3-nitrophenyl)acetate	Generator
NP-Hapten	HMDB
Hapten NP	HMDB
(4-Hydroxy-3-nitrophenyl)acetyl	HMDB
4-Hydroxy-3-nitrophenylacetyl	HMDB
3-Nitro-4-hydroxyphenylacetic acid	HMDB
4-OHNOPHAX	HMDB
4-Hydroxy-3-nitrophenyl acetyl	HMDB
4-Hydroxy-5-nitrophenyl acetic acid	HMDB
4-Hydroxy-3-nitrophenylacetate	Generator

Chemical Formula

C₈H₇NO₅

Average Molecular Weight

197.1449

Monoisotopic Molecular Weight

197.032422339

IUPAC Name

2-(4-hydroxy-3-nitrophenyl)acetic acid

Traditional Name

(4-hydroxy-3-nitrophenyl)acetic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CC1=CC(=C(O)C=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C8H7NO5/c10-7-2-1-5(4-8(11)12)3-6(7)9(13)14/h1-3,10H,4H2,(H,11,12)

InChI Key

QBHBHOSRLDPIHG-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
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
C-nitro compound
Organic nitro compound
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:546274 )

Ontology

Not Available

Urine (PMID: 12797864)

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 11997029)

Source

Exogenous

Exogenous (HMDB: HMDB0062403)

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	2.74 g/l	ALOGPS
LogP	1.14	ALOGPS

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.01	ALOGPS
logP	1.25	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.02	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.67 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	45.67 m³·mol⁻¹	ChemAxon
Polarizability	17.1 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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]+	144.154	31661259
DarkChem	[M-H]-	141.391	31661259
DeepCCS	[M+H]+	134.631	30932474
DeepCCS	[M-H]-	131.371	30932474
DeepCCS	[M-2H]-	167.251	30932474
DeepCCS	[M+Na]+	142.96	30932474
AllCCS	[M+H]+	140.8	32859911
AllCCS	[M+H-H2O]+	136.7	32859911
AllCCS	[M+NH4]+	144.7	32859911
AllCCS	[M+Na]+	145.8	32859911
AllCCS	[M-H]-	136.1	32859911
AllCCS	[M+Na-2H]-	136.5	32859911
AllCCS	[M+HCOO]-	137.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-hydroxy-3-nitrophenylacetate	OC(=O)CC1=CC(=C(O)C=C1)[N+]([O-])=O	2870.8	Standard polar	33892256
4-hydroxy-3-nitrophenylacetate	OC(=O)CC1=CC(=C(O)C=C1)[N+]([O-])=O	1558.1	Standard non polar	33892256
4-hydroxy-3-nitrophenylacetate	OC(=O)CC1=CC(=C(O)C=C1)[N+]([O-])=O	1762.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-hydroxy-3-nitrophenylacetate,1TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=C(O)C([N+](=O)[O-])=C1	1857.8	Semi standard non polar	33892256
4-hydroxy-3-nitrophenylacetate,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CC(=O)O)C=C1[N+](=O)[O-]	1892.3	Semi standard non polar	33892256
4-hydroxy-3-nitrophenylacetate,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC1=CC=C(O[Si](C)(C)C)C([N+](=O)[O-])=C1	1968.3	Semi standard non polar	33892256
4-hydroxy-3-nitrophenylacetate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=C(O)C([N+](=O)[O-])=C1	2108.8	Semi standard non polar	33892256
4-hydroxy-3-nitrophenylacetate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(=O)O)C=C1[N+](=O)[O-]	2194.1	Semi standard non polar	33892256
4-hydroxy-3-nitrophenylacetate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C([N+](=O)[O-])=C1	2455.9	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 - 4-hydroxy-3-nitrophenylacetate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-6900000000-e5a377fa30be1cf9599c	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-hydroxy-3-nitrophenylacetate 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 - 4-hydroxy-3-nitrophenylacetate 10V, Positive-QTOF	splash10-0002-0900000000-79a4c32d8d4140950f15	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 20V, Positive-QTOF	splash10-006x-0900000000-f46310eb481a53ce8a73	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 40V, Positive-QTOF	splash10-006y-2900000000-1198cd045e8ca04126ed	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 10V, Negative-QTOF	splash10-0002-0900000000-edf1df88d14334cd7609	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 20V, Negative-QTOF	splash10-0002-1900000000-de624db331c7d7c2ad29	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 40V, Negative-QTOF	splash10-0a4i-9400000000-fd42775792f6028d92ba	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 10V, Negative-QTOF	splash10-001i-0900000000-4322905b69ee20c9fe7b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 20V, Negative-QTOF	splash10-0zgi-0900000000-32060e9dd1d20b4cbfba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 40V, Negative-QTOF	splash10-0002-9600000000-ddfb1263633ffe02e608	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 10V, Positive-QTOF	splash10-0002-0900000000-cd198104c5c4f1e9625d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 20V, Positive-QTOF	splash10-0udj-0900000000-740cc01eff010d7e6826	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-hydroxy-3-nitrophenylacetate 40V, Positive-QTOF	splash10-0a4i-8900000000-e126a2d3aff76df1c47b	2021-09-23	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	11997029	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	12797864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB08294

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

447364

PDB ID

NPA

ChEBI ID

546274

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

Takahama U, Oniki T, Murata H: The presence of 4-hydroxyphenylacetic acid in human saliva and the possibility of its nitration by salivary nitrite in the stomach. FEBS Lett. 2002 May 8;518(1-3):116-8. [PubMed:11997029 ]
Mani AR, Pannala AS, Orie NN, Ollosson R, Harry D, Rice-Evans CA, Moore KP: Nitration of endogenous para-hydroxyphenylacetic acid and the metabolism of nitrotyrosine. Biochem J. 2003 Sep 1;374(Pt 2):521-7. [PubMed:12797864 ]

Showing metabocard for 4-hydroxy-3-nitrophenylacetate (HMDB0062403)

MOL for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)

3D MOL for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)

3D SDF for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)

3D-SDF for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)

PDB for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)

3D PDB for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)

SMILES for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)

INCHI for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)

Structure for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)

3D Structure for HMDB0062403 (4-hydroxy-3-nitrophenylacetate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra