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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:45:38 UTC

Update Date

2021-09-26 22:56:01 UTC

HMDB ID

HMDB0246745

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-Amino-2-nitrobenzoic acid

Description

5-Amino-2-nitrobenzoic acid belongs to the class of organic compounds known as nitrobenzoic acids and derivatives. Nitrobenzoic acids and derivatives are compounds containing a nitrobenzoic acid moiety, which consists of a benzene ring bearing both a carboxylic acid group and a nitro group on two different ring carbon atoms. Based on a literature review a significant number of articles have been published on 5-Amino-2-nitrobenzoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5-amino-2-nitrobenzoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5-Amino-2-nitrobenzoic acid 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


  Mrv1652309112101452D          

 13 13  0  0  0  0            999 V2000
    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 N   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
   -1.4289    0.0000    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
    0.7145   -1.2375    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  3 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  CHG  2  11   1  13  -1
M  END
> <DATABASE_ID>
HMDB0246745

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=CC(C(O)=O)=C(C=C1)[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H6N2O4/c8-4-1-2-6(9(12)13)5(3-4)7(10)11/h1-3H,8H2,(H,10,11)

> <INCHI_KEY>
KZZWQCKYLNIOBT-UHFFFAOYSA-N

> <FORMULA>
C7H6N2O4

> <MOLECULAR_WEIGHT>
182.135

> <EXACT_MASS>
182.032756681

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.74638830986038

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-amino-2-nitrobenzoic acid

> <ALOGPS_LOGP>
1.35

> <JCHEM_LOGP>
0.5330143898253398

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.341134418847002

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.367910631604072

> <JCHEM_PKA_STRONGEST_BASIC>
0.7500601039599811

> <JCHEM_POLAR_SURFACE_AREA>
106.46000000000001

> <JCHEM_REFRACTIVITY>
44.335100000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-amino-2-nitrobenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   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   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+1
HETATM   12  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O-1
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   11                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    4    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    3   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Amino-2-nitrobenzoate	Generator

Chemical Formula

C₇H₆N₂O₄

Average Molecular Weight

182.135

Monoisotopic Molecular Weight

182.032756681

IUPAC Name

5-amino-2-nitrobenzoic acid

Traditional Name

5-amino-2-nitrobenzoic acid

CAS Registry Number

Not Available

SMILES

NC1=CC(C(O)=O)=C(C=C1)[N+]([O-])=O

InChI Identifier

InChI=1S/C7H6N2O4/c8-4-1-2-6(9(12)13)5(3-4)7(10)11/h1-3H,8H2,(H,10,11)

InChI Key

KZZWQCKYLNIOBT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nitrobenzoic acids and derivatives. Nitrobenzoic acids and derivatives are compounds containing a nitrobenzoic acid moiety, which consists of a benzene ring bearing both a carboxylic acid group and a nitro group on two different ring carbon atoms.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Nitrobenzoic acids and derivatives

Alternative Parents

Substituents

Nitrobenzoate
Aminobenzoic acid
Aminobenzoic acid or derivatives
Benzoic acid
Nitrobenzene
Nitroaromatic compound
Benzoyl
Aniline or substituted anilines
Amino acid or derivatives
Amino acid
Organic nitro compound
C-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
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Primary amine
Organic zwitterion
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (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	1.35	ALOGPS
logP	0.53	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	2.37	ChemAxon
pKa (Strongest Basic)	0.75	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	106.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	44.34 m³·mol⁻¹	ChemAxon
Polarizability	15.75 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]+	129.15	30932474
DeepCCS	[M-H]-	125.889	30932474
DeepCCS	[M-2H]-	161.634	30932474
DeepCCS	[M+Na]+	137.359	30932474
AllCCS	[M+H]+	138.3	32859911
AllCCS	[M+H-H2O]+	134.0	32859911
AllCCS	[M+NH4]+	142.2	32859911
AllCCS	[M+Na]+	143.4	32859911
AllCCS	[M-H]-	131.9	32859911
AllCCS	[M+Na-2H]-	132.5	32859911
AllCCS	[M+HCOO]-	133.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Amino-2-nitrobenzoic acid	NC1=CC(C(O)=O)=C(C=C1)[N+]([O-])=O	3297.2	Standard polar	33892256
5-Amino-2-nitrobenzoic acid	NC1=CC(C(O)=O)=C(C=C1)[N+]([O-])=O	1959.2	Standard non polar	33892256
5-Amino-2-nitrobenzoic acid	NC1=CC(C(O)=O)=C(C=C1)[N+]([O-])=O	1983.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Amino-2-nitrobenzoic acid,2TMS,isomer #1	C[Si](C)(C)NC1=CC=C([N+](=O)[O-])C(C(=O)O[Si](C)(C)C)=C1	2044.1	Semi standard non polar	33892256
5-Amino-2-nitrobenzoic acid,2TMS,isomer #1	C[Si](C)(C)NC1=CC=C([N+](=O)[O-])C(C(=O)O[Si](C)(C)C)=C1	2043.7	Standard non polar	33892256
5-Amino-2-nitrobenzoic acid,2TMS,isomer #1	C[Si](C)(C)NC1=CC=C([N+](=O)[O-])C(C(=O)O[Si](C)(C)C)=C1	2240.0	Standard polar	33892256
5-Amino-2-nitrobenzoic acid,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=C([N+](=O)[O-])C(C(=O)O)=C1)[Si](C)(C)C	2029.1	Semi standard non polar	33892256
5-Amino-2-nitrobenzoic acid,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=C([N+](=O)[O-])C(C(=O)O)=C1)[Si](C)(C)C	2092.7	Standard non polar	33892256
5-Amino-2-nitrobenzoic acid,2TMS,isomer #2	C[Si](C)(C)N(C1=CC=C([N+](=O)[O-])C(C(=O)O)=C1)[Si](C)(C)C	2410.7	Standard polar	33892256
5-Amino-2-nitrobenzoic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1[N+](=O)[O-]	2058.5	Semi standard non polar	33892256
5-Amino-2-nitrobenzoic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1[N+](=O)[O-]	2082.7	Standard non polar	33892256
5-Amino-2-nitrobenzoic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C)[Si](C)(C)C)=CC=C1[N+](=O)[O-]	2121.5	Standard polar	33892256
5-Amino-2-nitrobenzoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C([N+](=O)[O-])C(C(=O)O[Si](C)(C)C(C)(C)C)=C1	2554.7	Semi standard non polar	33892256
5-Amino-2-nitrobenzoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C([N+](=O)[O-])C(C(=O)O[Si](C)(C)C(C)(C)C)=C1	2432.1	Standard non polar	33892256
5-Amino-2-nitrobenzoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C([N+](=O)[O-])C(C(=O)O[Si](C)(C)C(C)(C)C)=C1	2442.2	Standard polar	33892256
5-Amino-2-nitrobenzoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=C([N+](=O)[O-])C(C(=O)O)=C1)[Si](C)(C)C(C)(C)C	2564.3	Semi standard non polar	33892256
5-Amino-2-nitrobenzoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=C([N+](=O)[O-])C(C(=O)O)=C1)[Si](C)(C)C(C)(C)C	2431.5	Standard non polar	33892256
5-Amino-2-nitrobenzoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C1=CC=C([N+](=O)[O-])C(C(=O)O)=C1)[Si](C)(C)C(C)(C)C	2501.1	Standard polar	33892256
5-Amino-2-nitrobenzoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1[N+](=O)[O-]	2777.8	Semi standard non polar	33892256
5-Amino-2-nitrobenzoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1[N+](=O)[O-]	2657.8	Standard non polar	33892256
5-Amino-2-nitrobenzoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC=C1[N+](=O)[O-]	2428.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Amino-2-nitrobenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fl9-7900000000-5747ea3ab1c8fa02b1f3	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Amino-2-nitrobenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Amino-2-nitrobenzoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Amino-2-nitrobenzoic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Amino-2-nitrobenzoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Amino-2-nitrobenzoic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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

75159

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

83298

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

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 5-Amino-2-nitrobenzoic acid (HMDB0246745)

MOL for HMDB0246745 (5-Amino-2-nitrobenzoic acid)

3D MOL for HMDB0246745 (5-Amino-2-nitrobenzoic acid)

3D SDF for HMDB0246745 (5-Amino-2-nitrobenzoic acid)

3D-SDF for HMDB0246745 (5-Amino-2-nitrobenzoic acid)

PDB for HMDB0246745 (5-Amino-2-nitrobenzoic acid)

3D PDB for HMDB0246745 (5-Amino-2-nitrobenzoic acid)

SMILES for HMDB0246745 (5-Amino-2-nitrobenzoic acid)

INCHI for HMDB0246745 (5-Amino-2-nitrobenzoic acid)

Structure for HMDB0246745 (5-Amino-2-nitrobenzoic acid)

3D Structure for HMDB0246745 (5-Amino-2-nitrobenzoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra