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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:37:22 UTC

Update Date

2021-09-26 23:09:36 UTC

HMDB ID

HMDB0255085

Secondary Accession Numbers

None

Metabolite Identification

Common Name

n-benzoyl-d-alanine

Description

n-benzoyl-d-alanine, also known as a-methylhippate or methylhippuric acid, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. n-benzoyl-d-alanine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on n-benzoyl-d-alanine. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-benzoyl-d-alanine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically n-benzoyl-d-alanine 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

  Mrv1652309112116372D          

 14 14  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
  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
M  END
> <DATABASE_ID>
HMDB0255085

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(NC(=O)C1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO3/c1-7(10(13)14)11-9(12)8-5-3-2-4-6-8/h2-7H,1H3,(H,11,12)(H,13,14)

> <INCHI_KEY>
UAQVHNZEONHPQG-UHFFFAOYSA-N

> <FORMULA>
C10H11NO3

> <MOLECULAR_WEIGHT>
193.202

> <EXACT_MASS>
193.073893218

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.480277324221902

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(phenylformamido)propanoic acid

> <ALOGPS_LOGP>
0.88

> <JCHEM_LOGP>
1.0943097266666664

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.17817702616037

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.659945302706831

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3198359941230495

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
50.611600000000024

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylhippuric 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  -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
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                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
alpha-Methylhippuric acid	ChEBI
Benzoyl-DL-alanine	ChEBI
Benzoylalanine	ChEBI
DL-N-Benzoylalanine	ChEBI
Methylhippuric acid	ChEBI
N-Benzoyl-DL-alanine	ChEBI
a-Methylhippate	Generator
a-Methylhippic acid	Generator
alpha-Methylhippate	Generator
alpha-Methylhippic acid	Generator
Α-methylhippate	Generator
Α-methylhippic acid	Generator
Methylhippate	Generator
Methylhippic acid	Generator
N-Benzoyl-beta-alanine	HMDB
N-Benzoylalanine monosodium salt, (L-ala)-isomer	HMDB
N-Benzoylalanine, (D-ala)-isomer	HMDB
N-Benzoylalanine, (DL-ala)-isomer	HMDB
N-Benzoylalanine, (beta-ala)-isomer	HMDB
Betamipron	HMDB
N-Benzoylalanine	HMDB
N-Benzoyl-D-alanine	MeSH

Chemical Formula

C₁₀H₁₁NO₃

Average Molecular Weight

193.202

Monoisotopic Molecular Weight

193.073893218

IUPAC Name

2-(phenylformamido)propanoic acid

Traditional Name

methylhippuric acid

CAS Registry Number

Not Available

SMILES

CC(NC(=O)C1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C10H11NO3/c1-7(10(13)14)11-9(12)8-5-3-2-4-6-8/h2-7H,1H3,(H,11,12)(H,13,14)

InChI Key

UAQVHNZEONHPQG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Alanine or derivatives
Monocyclic benzene moiety
Benzenoid
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
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

N-acyl-amino acid (CHEBI:71167 )
alanine derivative (CHEBI:71167 )

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	0.88	ALOGPS
logP	1.09	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.66	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	50.61 m³·mol⁻¹	ChemAxon
Polarizability	19.48 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]+	138.47	30932474
DeepCCS	[M-H]-	134.642	30932474
DeepCCS	[M-2H]-	172.015	30932474
DeepCCS	[M+Na]+	147.554	30932474
AllCCS	[M+H]+	143.2	32859911
AllCCS	[M+H-H2O]+	139.2	32859911
AllCCS	[M+NH4]+	147.0	32859911
AllCCS	[M+Na]+	148.0	32859911
AllCCS	[M-H]-	142.4	32859911
AllCCS	[M+Na-2H]-	143.1	32859911
AllCCS	[M+HCOO]-	143.9	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
n-benzoyl-d-alanine,1TMS,isomer #1	CC(NC(=O)C1=CC=CC=C1)C(=O)O[Si](C)(C)C	1838.7	Semi standard non polar	33892256
n-benzoyl-d-alanine,1TMS,isomer #1	CC(NC(=O)C1=CC=CC=C1)C(=O)O[Si](C)(C)C	1729.9	Standard non polar	33892256
n-benzoyl-d-alanine,1TMS,isomer #1	CC(NC(=O)C1=CC=CC=C1)C(=O)O[Si](C)(C)C	2243.2	Standard polar	33892256
n-benzoyl-d-alanine,1TMS,isomer #2	CC(C(=O)O)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C	1777.6	Semi standard non polar	33892256
n-benzoyl-d-alanine,1TMS,isomer #2	CC(C(=O)O)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C	1740.0	Standard non polar	33892256
n-benzoyl-d-alanine,1TMS,isomer #2	CC(C(=O)O)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C	2352.3	Standard polar	33892256
n-benzoyl-d-alanine,2TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C	1795.9	Semi standard non polar	33892256
n-benzoyl-d-alanine,2TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C	1784.5	Standard non polar	33892256
n-benzoyl-d-alanine,2TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C	2058.5	Standard polar	33892256
n-benzoyl-d-alanine,1TBDMS,isomer #1	CC(NC(=O)C1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2075.5	Semi standard non polar	33892256
n-benzoyl-d-alanine,1TBDMS,isomer #1	CC(NC(=O)C1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	1929.9	Standard non polar	33892256
n-benzoyl-d-alanine,1TBDMS,isomer #1	CC(NC(=O)C1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C	2372.5	Standard polar	33892256
n-benzoyl-d-alanine,1TBDMS,isomer #2	CC(C(=O)O)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2024.1	Semi standard non polar	33892256
n-benzoyl-d-alanine,1TBDMS,isomer #2	CC(C(=O)O)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	1935.5	Standard non polar	33892256
n-benzoyl-d-alanine,1TBDMS,isomer #2	CC(C(=O)O)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2455.5	Standard polar	33892256
n-benzoyl-d-alanine,2TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2257.0	Semi standard non polar	33892256
n-benzoyl-d-alanine,2TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2192.7	Standard non polar	33892256
n-benzoyl-d-alanine,2TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2342.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - n-benzoyl-d-alanine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1900000000-5eb041b52404379a9de5	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - n-benzoyl-d-alanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - n-benzoyl-d-alanine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	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

64163

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71002

PDB ID

Not Available

ChEBI ID

71167

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 n-benzoyl-d-alanine (HMDB0255085)

MOL for HMDB0255085 (n-benzoyl-d-alanine)

3D MOL for HMDB0255085 (n-benzoyl-d-alanine)

3D SDF for HMDB0255085 (n-benzoyl-d-alanine)

3D-SDF for HMDB0255085 (n-benzoyl-d-alanine)

PDB for HMDB0255085 (n-benzoyl-d-alanine)

3D PDB for HMDB0255085 (n-benzoyl-d-alanine)

SMILES for HMDB0255085 (n-benzoyl-d-alanine)

INCHI for HMDB0255085 (n-benzoyl-d-alanine)

Structure for HMDB0255085 (n-benzoyl-d-alanine)

3D Structure for HMDB0255085 (n-benzoyl-d-alanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

NMR Spectra