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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 20:50:51 UTC

Update Date

2021-09-26 22:50:44 UTC

HMDB ID

HMDB0243594

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid

Description

(2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine. Based on a literature review very few articles have been published on (2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (2s)-2-[(3-nitrobenzoyl)amino]propanoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (2S)-2-[(3-Nitrobenzoyl)amino]propanoic 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


  Mrv1652309102122512D          

 17 17  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  CHG  2  15   1  17  -1
M  END
> <DATABASE_ID>
HMDB0243594

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H10N2O5/c1-6(10(14)15)11-9(13)7-3-2-4-8(5-7)12(16)17/h2-6H,1H3,(H,11,13)(H,14,15)

> <INCHI_KEY>
CDBXKLYOJGRINM-UHFFFAOYSA-N

> <FORMULA>
C10H10N2O5

> <MOLECULAR_WEIGHT>
238.199

> <EXACT_MASS>
238.05897143

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.91110502709977

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3-nitrophenyl)formamido]propanoic acid

> <ALOGPS_LOGP>
1.20

> <JCHEM_LOGP>
1.0342939160000002

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.82357630810009

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.8111865635379605

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5798890810403785

> <JCHEM_POLAR_SURFACE_AREA>
109.54000000000002

> <JCHEM_REFRACTIVITY>
56.93210000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3-nitrophenyl)formamido]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       4.001  -5.390   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0      10.669  -4.620   0.000  0.00  0.00           N+1
HETATM   16  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
CONECT   15   11   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0243594
HETATM    1  C1  UNL     1      -3.374   1.215  -0.642  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.727   0.028   0.044  1.00  0.00           C  
HETATM    3  N1  UNL     1      -1.386  -0.087  -0.492  1.00  0.00           N  
HETATM    4  C3  UNL     1      -0.299   0.117   0.393  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.505   0.392   1.617  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.086   0.022  -0.055  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.388  -0.272  -1.366  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.700  -0.354  -1.757  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.717  -0.145  -0.846  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.462   0.152   0.475  1.00  0.00           C  
HETATM   11  N2  UNL     1       4.522   0.363   1.393  1.00  0.00           N1+
HETATM   12  O2  UNL     1       4.293   0.629   2.578  1.00  0.00           O  
HETATM   13  O3  UNL     1       5.810   0.266   0.937  1.00  0.00           O1-
HETATM   14  C9  UNL     1       2.131   0.229   0.845  1.00  0.00           C  
HETATM   15  C10 UNL     1      -3.494  -1.210  -0.119  1.00  0.00           C  
HETATM   16  O4  UNL     1      -3.044  -2.253  -0.660  1.00  0.00           O  
HETATM   17  O5  UNL     1      -4.800  -1.240   0.352  1.00  0.00           O  
HETATM   18  H1  UNL     1      -2.811   1.530  -1.553  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.385   0.929  -0.966  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.434   2.095   0.013  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.723   0.275   1.137  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.280  -0.309  -1.480  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.632  -0.444  -2.114  1.00  0.00           H  
HETATM   24  H7  UNL     1       2.930  -0.587  -2.793  1.00  0.00           H  
HETATM   25  H8  UNL     1       4.757  -0.208  -1.145  1.00  0.00           H  
HETATM   26  H9  UNL     1       1.897   0.458   1.865  1.00  0.00           H  
HETATM   27  H10 UNL     1      -5.062  -1.593   1.259  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   15   21
CONECT    3    4   22
CONECT    4    5    5    6
CONECT    6    7    7   14
CONECT    7    8   23
CONECT    8    9    9   24
CONECT    9   10   25
CONECT   10   11   14   14
CONECT   11   12   12   13
CONECT   14   26
CONECT   15   16   16   17
CONECT   17   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S)-2-[(3-Nitrobenzoyl)amino]propanoate	Generator

Chemical Formula

C₁₀H₁₀N₂O₅

Average Molecular Weight

238.199

Monoisotopic Molecular Weight

238.05897143

IUPAC Name

2-[(3-nitrophenyl)formamido]propanoic acid

Traditional Name

2-[(3-nitrophenyl)formamido]propanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H10N2O5/c1-6(10(14)15)11-9(13)7-3-2-4-8(5-7)12(16)17/h2-6H,1H3,(H,11,13)(H,14,15)

InChI Key

CDBXKLYOJGRINM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hippuric acids

Alternative Parents

Substituents

N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Hippuric acid
Alanine or derivatives
Alpha-amino acid or derivatives
Nitrobenzene
Nitroaromatic compound
Benzoyl
Carboxamide group
Organic nitro compound
C-nitro compound
Secondary carboxylic acid amide
Allyl-type 1,3-dipolar organic compound
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Organic oxoazanium
Organic 1,3-dipolar compound
Carboxylic acid
Carboxylic acid derivative
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic zwitterion
Organic salt
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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)

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	1.2	ALOGPS
logP	1.03	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	2.81	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.54 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	56.93 m³·mol⁻¹	ChemAxon
Polarizability	21.91 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
DeepCCS	[M+H]+	156.017	30932474
DeepCCS	[M-H]-	153.83	30932474
DeepCCS	[M-2H]-	187.072	30932474
DeepCCS	[M+Na]+	162.11	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid	CC(NC(=O)C1=CC(=CC=C1)[N+]([O-])=O)C(O)=O	3284.8	Standard polar	33892256
(2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid	CC(NC(=O)C1=CC(=CC=C1)[N+]([O-])=O)C(O)=O	2089.8	Standard non polar	33892256
(2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid	CC(NC(=O)C1=CC(=CC=C1)[N+]([O-])=O)C(O)=O	2200.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid,2TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)N(C(=O)C1=CC=CC([N+](=O)[O-])=C1)[Si](C)(C)C	2178.4	Semi standard non polar	33892256
(2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid,2TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)N(C(=O)C1=CC=CC([N+](=O)[O-])=C1)[Si](C)(C)C	2100.7	Standard non polar	33892256
(2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid,2TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)N(C(=O)C1=CC=CC([N+](=O)[O-])=C1)[Si](C)(C)C	2568.4	Standard polar	33892256
(2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid,2TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)C1=CC=CC([N+](=O)[O-])=C1)[Si](C)(C)C(C)(C)C	2709.7	Semi standard non polar	33892256
(2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid,2TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)C1=CC=CC([N+](=O)[O-])=C1)[Si](C)(C)C(C)(C)C	2540.9	Standard non polar	33892256
(2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid,2TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)C1=CC=CC([N+](=O)[O-])=C1)[Si](C)(C)C(C)(C)C	2743.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0096-6920000000-2e746f5beef273976047	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2S)-2-[(3-Nitrobenzoyl)amino]propanoic 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

2670753

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3427405

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 (2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid (HMDB0243594)

MOL for HMDB0243594 ((2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid)

3D MOL for HMDB0243594 ((2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid)

3D SDF for HMDB0243594 ((2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid)

3D-SDF for HMDB0243594 ((2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid)

PDB for HMDB0243594 ((2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid)

3D PDB for HMDB0243594 ((2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid)

SMILES for HMDB0243594 ((2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid)

INCHI for HMDB0243594 ((2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid)

Structure for HMDB0243594 ((2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid)

3D Structure for HMDB0243594 ((2S)-2-[(3-Nitrobenzoyl)amino]propanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra