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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:53:08 UTC

Update Date

2021-09-26 22:52:42 UTC

HMDB ID

HMDB0244748

Secondary Accession Numbers

None

Metabolite Identification

Common Name

L-Alanine-4-nitroanilide

Description

L-Alanine-4-nitroanilide belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. Based on a literature review very few articles have been published on L-Alanine-4-nitroanilide. This compound has been identified in human blood as reported by (PMID: 31557052 ). L-alanine-4-nitroanilide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically L-Alanine-4-nitroanilide 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

  Mrv1652309102123532D          

 15 15  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   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 N   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
    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
    0.7145    3.7125    0.0000 N   0  0  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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  2 15  1  0  0  0  0
M  CHG  2  12   1  14  -1
M  END
> <DATABASE_ID>
HMDB0244748

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H11N3O3/c1-6(10)9(13)11-7-2-4-8(5-3-7)12(14)15/h2-6H,10H2,1H3,(H,11,13)

> <INCHI_KEY>
PXFUDSMGEYRNNC-UHFFFAOYSA-N

> <FORMULA>
C9H11N3O3

> <MOLECULAR_WEIGHT>
209.205

> <EXACT_MASS>
209.080041226

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.358715849916223

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-amino-N-(4-nitrophenyl)propanamide

> <ALOGPS_LOGP>
0.24

> <JCHEM_LOGP>
0.7955747723333331

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.406867943257154

> <JCHEM_PKA_STRONGEST_BASIC>
8.226952776961625

> <JCHEM_POLAR_SURFACE_AREA>
98.25999999999999

> <JCHEM_REFRACTIVITY>
55.0951

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.01e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-N-(4-nitrophenyl)propanamide

> <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      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       1.334   3.850   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+1
HETATM   13  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O-1
HETATM   15  N   UNK     0       1.334   6.930   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    2                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₉H₁₁N₃O₃

Average Molecular Weight

209.205

Monoisotopic Molecular Weight

209.080041226

IUPAC Name

2-amino-N-(4-nitrophenyl)propanamide

Traditional Name

2-amino-N-(4-nitrophenyl)propanamide

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C9H11N3O3/c1-6(10)9(13)11-7-2-4-8(5-3-7)12(14)15/h2-6H,10H2,1H3,(H,11,13)

InChI Key

PXFUDSMGEYRNNC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid amides

Alternative Parents

Substituents

Alpha-amino acid amide
Alanine or derivatives
Nitrobenzene
Anilide
Nitroaromatic compound
N-arylamide
Monocyclic benzene moiety
Benzenoid
Carboxamide group
C-nitro compound
Secondary carboxylic acid amide
Organic nitro compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Allyl-type 1,3-dipolar organic compound
Organic oxoazanium
Organic oxygen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Amine
Primary aliphatic amine
Organic nitrogen compound
Carbonyl group
Organic oxide
Organic zwitterion
Hydrocarbon derivative
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	0.24	ALOGPS
logP	0.8	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.41	ChemAxon
pKa (Strongest Basic)	8.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	98.26 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	55.1 m³·mol⁻¹	ChemAxon
Polarizability	20.36 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]+	142.839	30932474
DeepCCS	[M-H]-	139.579	30932474
DeepCCS	[M-2H]-	174.89	30932474
DeepCCS	[M+Na]+	150.967	30932474
AllCCS	[M+H]+	147.0	32859911
AllCCS	[M+H-H2O]+	143.2	32859911
AllCCS	[M+NH4]+	150.5	32859911
AllCCS	[M+Na]+	151.5	32859911
AllCCS	[M-H]-	145.6	32859911
AllCCS	[M+Na-2H]-	146.2	32859911
AllCCS	[M+HCOO]-	146.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Alanine-4-nitroanilide	CC(N)C(=O)NC1=CC=C(C=C1)[N+]([O-])=O	3149.9	Standard polar	33892256
L-Alanine-4-nitroanilide	CC(N)C(=O)NC1=CC=C(C=C1)[N+]([O-])=O	2190.4	Standard non polar	33892256
L-Alanine-4-nitroanilide	CC(N)C(=O)NC1=CC=C(C=C1)[N+]([O-])=O	2187.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Alanine-4-nitroanilide,1TMS,isomer #1	CC(N[Si](C)(C)C)C(=O)NC1=CC=C([N+](=O)[O-])C=C1	2249.7	Semi standard non polar	33892256
L-Alanine-4-nitroanilide,1TMS,isomer #1	CC(N[Si](C)(C)C)C(=O)NC1=CC=C([N+](=O)[O-])C=C1	2087.0	Standard non polar	33892256
L-Alanine-4-nitroanilide,1TMS,isomer #1	CC(N[Si](C)(C)C)C(=O)NC1=CC=C([N+](=O)[O-])C=C1	2903.9	Standard polar	33892256
L-Alanine-4-nitroanilide,1TMS,isomer #2	CC(N)C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C	2002.2	Semi standard non polar	33892256
L-Alanine-4-nitroanilide,1TMS,isomer #2	CC(N)C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C	2011.9	Standard non polar	33892256
L-Alanine-4-nitroanilide,1TMS,isomer #2	CC(N)C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C	3011.0	Standard polar	33892256
L-Alanine-4-nitroanilide,2TMS,isomer #1	CC(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)N([Si](C)(C)C)[Si](C)(C)C	2391.3	Semi standard non polar	33892256
L-Alanine-4-nitroanilide,2TMS,isomer #1	CC(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)N([Si](C)(C)C)[Si](C)(C)C	2195.0	Standard non polar	33892256
L-Alanine-4-nitroanilide,2TMS,isomer #1	CC(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)N([Si](C)(C)C)[Si](C)(C)C	2714.2	Standard polar	33892256
L-Alanine-4-nitroanilide,2TMS,isomer #2	CC(N[Si](C)(C)C)C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C	2088.4	Semi standard non polar	33892256
L-Alanine-4-nitroanilide,2TMS,isomer #2	CC(N[Si](C)(C)C)C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C	2101.7	Standard non polar	33892256
L-Alanine-4-nitroanilide,2TMS,isomer #2	CC(N[Si](C)(C)C)C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C	2467.7	Standard polar	33892256
L-Alanine-4-nitroanilide,3TMS,isomer #1	CC(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2233.4	Semi standard non polar	33892256
L-Alanine-4-nitroanilide,3TMS,isomer #1	CC(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2238.2	Standard non polar	33892256
L-Alanine-4-nitroanilide,3TMS,isomer #1	CC(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2364.3	Standard polar	33892256
L-Alanine-4-nitroanilide,1TBDMS,isomer #1	CC(N[Si](C)(C)C(C)(C)C)C(=O)NC1=CC=C([N+](=O)[O-])C=C1	2499.3	Semi standard non polar	33892256
L-Alanine-4-nitroanilide,1TBDMS,isomer #1	CC(N[Si](C)(C)C(C)(C)C)C(=O)NC1=CC=C([N+](=O)[O-])C=C1	2286.2	Standard non polar	33892256
L-Alanine-4-nitroanilide,1TBDMS,isomer #1	CC(N[Si](C)(C)C(C)(C)C)C(=O)NC1=CC=C([N+](=O)[O-])C=C1	2932.5	Standard polar	33892256
L-Alanine-4-nitroanilide,1TBDMS,isomer #2	CC(N)C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C	2313.0	Semi standard non polar	33892256
L-Alanine-4-nitroanilide,1TBDMS,isomer #2	CC(N)C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C	2213.1	Standard non polar	33892256
L-Alanine-4-nitroanilide,1TBDMS,isomer #2	CC(N)C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C	3022.5	Standard polar	33892256
L-Alanine-4-nitroanilide,2TBDMS,isomer #1	CC(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2891.3	Semi standard non polar	33892256
L-Alanine-4-nitroanilide,2TBDMS,isomer #1	CC(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2611.3	Standard non polar	33892256
L-Alanine-4-nitroanilide,2TBDMS,isomer #1	CC(C(=O)NC1=CC=C([N+](=O)[O-])C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2770.3	Standard polar	33892256
L-Alanine-4-nitroanilide,2TBDMS,isomer #2	CC(N[Si](C)(C)C(C)(C)C)C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C	2628.4	Semi standard non polar	33892256
L-Alanine-4-nitroanilide,2TBDMS,isomer #2	CC(N[Si](C)(C)C(C)(C)C)C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C	2544.3	Standard non polar	33892256
L-Alanine-4-nitroanilide,2TBDMS,isomer #2	CC(N[Si](C)(C)C(C)(C)C)C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C	2631.5	Standard polar	33892256
L-Alanine-4-nitroanilide,3TBDMS,isomer #1	CC(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3009.2	Semi standard non polar	33892256
L-Alanine-4-nitroanilide,3TBDMS,isomer #1	CC(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2853.8	Standard non polar	33892256
L-Alanine-4-nitroanilide,3TBDMS,isomer #1	CC(C(=O)N(C1=CC=C([N+](=O)[O-])C=C1)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2602.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - L-Alanine-4-nitroanilide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9400000000-a9c54dc88c14ac7639b1	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Alanine-4-nitroanilide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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

471645

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

541605

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 L-Alanine-4-nitroanilide (HMDB0244748)

MOL for HMDB0244748 (L-Alanine-4-nitroanilide)

3D MOL for HMDB0244748 (L-Alanine-4-nitroanilide)

3D SDF for HMDB0244748 (L-Alanine-4-nitroanilide)

3D-SDF for HMDB0244748 (L-Alanine-4-nitroanilide)

PDB for HMDB0244748 (L-Alanine-4-nitroanilide)

3D PDB for HMDB0244748 (L-Alanine-4-nitroanilide)

SMILES for HMDB0244748 (L-Alanine-4-nitroanilide)

INCHI for HMDB0244748 (L-Alanine-4-nitroanilide)

Structure for HMDB0244748 (L-Alanine-4-nitroanilide)

3D Structure for HMDB0244748 (L-Alanine-4-nitroanilide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra