NP-MRD: Showing NP-Card for (4-hydroxy-3-nitrophenyl)acetic acid (NP0274026)

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Record Information

Version

1.0

Created at

2022-09-08 21:16:08 UTC

Updated at

2022-09-08 21:16:08 UTC

NP-MRD ID

NP0274026

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4-hydroxy-3-nitrophenyl)acetic acid

Description

4-Hydroxy-3-nitrophenylacetate, also known as NO2HPA or NP-hapten, 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-hydroxy-3-nitrophenyl)acetic acid is found in Jeotgalibacillus marinus, Pyricularia oryzae and Sinapis alba. It was first documented in 1981 (PMID: 6787594). Based on a literature review a significant number of articles have been published on 4-hydroxy-3-nitrophenylacetate (PMID: 11997029) (PMID: 14687937) (PMID: 24383944) (PMID: 7765721).

Structure

MOL 3D MOL SDF 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>
NP0274026

> <DATABASE_NAME>
NP-MRD

> <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

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 Mass

197.1449 Da

Monoisotopic Mass

197.03242 Da

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bacillus marinus	LOTUS Database	35616633
Pyricularia oryzae	LOTUS Database	35616633
Sinapis alba	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted 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

External Links

HMDB ID

HMDB0062403

DrugBank ID

DB08294

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]
Tobita T, Oda M, Azuma T: Segmental flexibility and avidity of IgM in the interaction of polyvalent antigens. Mol Immunol. 2004 Jan;40(11):803-11. doi: 10.1016/j.molimm.2003.09.011. [PubMed:14687937 ]
Kallberg E, Ivars F, Leanderson T: Quinoline-3-carboxamides modulate primary T cell-dependent B cell responses but do not inhibit functional immunity. Scand J Immunol. 2014 Apr;79(4):237-43. doi: 10.1111/sji.12152. [PubMed:24383944 ]
Lonai P, Puri J, Hammerling G: H-2-restricted antigen binding by a hybridoma clone that produces antigen-specific helper factor. Proc Natl Acad Sci U S A. 1981 Jan;78(1):549-53. doi: 10.1073/pnas.78.1.549. [PubMed:6787594 ]
Watanabe M, Watanabe J, Michigami Y: Enhancing effect of 4-hydroxy-3-nitrophenylacetic acid on transcription of the ice nucleation-active gene of Xanthomonas campestris. Biosci Biotechnol Biochem. 1994 Dec;58(12):2269-70. doi: 10.1271/bbb.58.2269. [PubMed:7765721 ]
LOTUS database [Link]

Showing NP-Card for (4-hydroxy-3-nitrophenyl)acetic acid (NP0274026)

MOL for NP0274026 ((4-hydroxy-3-nitrophenyl)acetic acid)

3D MOL for NP0274026 ((4-hydroxy-3-nitrophenyl)acetic acid)

3D SDF for NP0274026 ((4-hydroxy-3-nitrophenyl)acetic acid)

3D-SDF for NP0274026 ((4-hydroxy-3-nitrophenyl)acetic acid)

PDB for NP0274026 ((4-hydroxy-3-nitrophenyl)acetic acid)

3D PDB for NP0274026 ((4-hydroxy-3-nitrophenyl)acetic acid)

SMILES for NP0274026 ((4-hydroxy-3-nitrophenyl)acetic acid)

INCHI for NP0274026 ((4-hydroxy-3-nitrophenyl)acetic acid)

Structure for NP0274026 ((4-hydroxy-3-nitrophenyl)acetic acid)

3D Structure for NP0274026 ((4-hydroxy-3-nitrophenyl)acetic acid)