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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:48:22 UTC

Update Date

2021-09-26 23:09:51 UTC

HMDB ID

HMDB0255227

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Phenylglycine

Description

N-Phenylglycine, also known as NPG or anilinoacetate, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Based on a literature review a significant number of articles have been published on N-Phenylglycine. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-phenylglycine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-Phenylglycine 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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Anilinoacetic acid	ChEBI
NPG	ChEBI
Anilinoacetate	Generator
N-Phenylglycine, potassium salt	MeSH
N-Phenylglycine, sodium salt	MeSH

Chemical Formula

C₈H₉NO₂

Average Molecular Weight

151.165

Monoisotopic Molecular Weight

151.063328534

IUPAC Name

2-(phenylamino)acetic acid

Traditional Name

N-phenylglycine

CAS Registry Number

Not Available

SMILES

OC(=O)CNC1=CC=CC=C1

InChI Identifier

InChI=1S/C8H9NO2/c10-8(11)6-9-7-4-2-1-3-5-7/h1-5,9H,6H2,(H,10,11)

InChI Key

NPKSPKHJBVJUKB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

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 acids

Alternative Parents

Substituents

Alpha-amino acid
Aniline or substituted anilines
Phenylalkylamine
Secondary aliphatic/aromatic amine
Monocyclic benzene moiety
Benzenoid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Secondary amine
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic alpha-amino acid (CHEBI:55477 )

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	0.73	ALOGPS
logP	-0.16	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	2.63	ChemAxon
pKa (Strongest Basic)	5.66	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	42.34 m³·mol⁻¹	ChemAxon
Polarizability	15.46 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]+	130.898	30932474
DeepCCS	[M-H]-	127.48	30932474
DeepCCS	[M-2H]-	164.607	30932474
DeepCCS	[M+Na]+	140.057	30932474
AllCCS	[M+H]+	132.6	32859911
AllCCS	[M+H-H2O]+	128.2	32859911
AllCCS	[M+NH4]+	136.8	32859911
AllCCS	[M+Na]+	137.9	32859911
AllCCS	[M-H]-	130.9	32859911
AllCCS	[M+Na-2H]-	132.3	32859911
AllCCS	[M+HCOO]-	133.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Phenylglycine	OC(=O)CNC1=CC=CC=C1	2104.2	Standard polar	33892256
N-Phenylglycine	OC(=O)CNC1=CC=CC=C1	1484.5	Standard non polar	33892256
N-Phenylglycine	OC(=O)CNC1=CC=CC=C1	1546.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Phenylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C1=CC=CC=C1)[Si](C)(C)C	1581.3	Semi standard non polar	33892256
N-Phenylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C1=CC=CC=C1)[Si](C)(C)C	1621.2	Standard non polar	33892256
N-Phenylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C1=CC=CC=C1)[Si](C)(C)C	1794.0	Standard polar	33892256
N-Phenylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2035.7	Semi standard non polar	33892256
N-Phenylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2073.8	Standard non polar	33892256
N-Phenylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2095.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Phenylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1900000000-e0cf5e9e88aa85d49bed	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Phenylglycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Phenylglycine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Phenylglycine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Phenylglycine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Phenylglycine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Phenylglycine 10V, Positive-QTOF	splash10-0a4i-0900000000-7838c746f5f82bb1853f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Phenylglycine 20V, Positive-QTOF	splash10-0a4i-3900000000-12ee614016fab32ad3be	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Phenylglycine 10V, Positive-QTOF	splash10-0a4i-1900000000-ae87b9da46ceef02324f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Phenylglycine 30V, Positive-QTOF	splash10-004i-9100000000-4682e352980b2b2fb74d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Phenylglycine 10V, Positive-QTOF	splash10-0a4i-3900000000-3aaea706bb8112530f1f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Phenylglycine 0V, Positive-QTOF	splash10-0pb9-0900000000-9b25eca83d51410f97be	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Phenylglycine 30V, Positive-QTOF	splash10-004i-9100000000-0ad0f3c6eac34c3e0e6d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Phenylglycine 0V, Positive-QTOF	splash10-0pb9-0900000000-8154416df5da35a7d51d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Phenylglycine 30V, Positive-QTOF	splash10-056r-9300000000-6fa1542fa5c207e6c845	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - N-Phenylglycine 40V, Positive-QTOF	splash10-004i-9000000000-faa94d38a70f30cf2439	2021-09-20	HMDB team, MONA	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	¹H NMR Spectrum (1D, 200 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	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	¹H NMR Spectrum (1D, 400 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, 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	¹H NMR Spectrum (1D, 600 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, 700 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, 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

59416

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

N-Phenylglycine

METLIN ID

Not Available

PubChem Compound

66025

PDB ID

Not Available

ChEBI ID

55477

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-Phenylglycine (HMDB0255227)

MOL for HMDB0255227 (N-Phenylglycine)

3D MOL for HMDB0255227 (N-Phenylglycine)

3D SDF for HMDB0255227 (N-Phenylglycine)

3D-SDF for HMDB0255227 (N-Phenylglycine)

PDB for HMDB0255227 (N-Phenylglycine)

3D PDB for HMDB0255227 (N-Phenylglycine)

SMILES for HMDB0255227 (N-Phenylglycine)

INCHI for HMDB0255227 (N-Phenylglycine)

Structure for HMDB0255227 (N-Phenylglycine)

3D Structure for HMDB0255227 (N-Phenylglycine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra