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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 14:32:12 UTC

Update Date

2021-09-26 23:09:29 UTC

HMDB ID

HMDB0255011

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-(4-Hydroxyphenyl)glycine

Description

N-(4-Hydroxyphenyl)glycine, also known as N-PHPG or 4-(carboxymethylamino)phenol, 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-(4-Hydroxyphenyl)glycine. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-(4-hydroxyphenyl)glycine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-(4-Hydroxyphenyl)glycine 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

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      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000   6.160   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    3                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-(Carboxymethylamino)phenol	ChEBI
D,L-(4-Hydroxyphenyl)glycine	ChEBI
Glycin	ChEBI
Hydroxyphenyl glycine	ChEBI
N-4-Hydroxyphenylglycine	ChEBI
N-p-Hydroxyphenylglycine	ChEBI
N-PHPG	ChEBI
NPHPG	ChEBI
p-Hydroxyanilinoacetic acid	ChEBI
p-Hydroxyphenyl glycine	ChEBI
p-Hydroxyphenylaminoacetic acid	ChEBI
p-Hydroxyphenylglycine	ChEBI
Para-hydroxyphenyl glycine	ChEBI
Photoglycine	ChEBI
PHPG	ChEBI
p-Hydroxyanilinoacetate	Generator
p-Hydroxyphenylaminoacetate	Generator
(R,S)-3HPG	MeSH
4-Hydroxyphenylglycine	MeSH
4-Hydroxyphenylglycine hydrobromide, (+-)-isomer	MeSH
4-Hydroxyphenylglycine hydrochloride, (R)-isomer	MeSH
4-Hydroxyphenylglycine perchlorate, (+-)-isomer	MeSH
4-Hydroxyphenylglycine, (+-)-isomer	MeSH
4-Hydroxyphenylglycine, (R)-isomer	MeSH
4-Hydroxyphenylglycine, (S)-isomer	MeSH
4-Hydroxyphenylglycine, 2,4-dimethylbenzenesulfonate, (+-)-isomer	MeSH
4-Hydroxyphenylglycine, 2,4-dimethylbenzenesulfonate, (R)-isomer	MeSH
4-Hydroxyphenylglycine, 4-methylbenzenesulfonate, (+-)-isomer	MeSH
4-Hydroxyphenylglycine, 4-methylbenzenesulfonate, (S)-isomer	MeSH
4-Hydroxyphenylglycine, monosodium salt	MeSH
4-Hydroxyphenylglycine, monosodium salt, (R)-isomer	MeSH
D-p-Hydroxyphenylglycine	MeSH
L-4-Hydroxyphenylglycine	MeSH
Oxfenicine	MeSH

Chemical Formula

C₈H₉NO₃

Average Molecular Weight

167.164

Monoisotopic Molecular Weight

167.058243154

IUPAC Name

2-[(4-hydroxyphenyl)amino]acetic acid

Traditional Name

glycin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C8H9NO3/c10-7-3-1-6(2-4-7)9-5-8(11)12/h1-4,9-10H,5H2,(H,11,12)

InChI Key

WRUZLCLJULHLEY-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
P-aminophenol
Aminophenol
Phenylalkylamine
Aniline or substituted anilines
1-hydroxy-2-unsubstituted benzenoid
Phenol
Secondary aliphatic/aromatic amine
Monocyclic benzene moiety
Benzenoid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Secondary amine
Organooxygen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

glycine derivative (CHEBI:55443 )
phenols (CHEBI:55443 )
non-proteinogenic alpha-amino acid (CHEBI:55443 )

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	0.64	ALOGPS
logP	-1.1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	2.32	ChemAxon
pKa (Strongest Basic)	6.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	44.32 m³·mol⁻¹	ChemAxon
Polarizability	16.48 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]+	135.688	30932474
DeepCCS	[M-H]-	132.777	30932474
DeepCCS	[M-2H]-	169.707	30932474
DeepCCS	[M+Na]+	145.245	30932474
AllCCS	[M+H]+	136.3	32859911
AllCCS	[M+H-H2O]+	132.0	32859911
AllCCS	[M+NH4]+	140.3	32859911
AllCCS	[M+Na]+	141.4	32859911
AllCCS	[M-H]-	134.8	32859911
AllCCS	[M+Na-2H]-	135.9	32859911
AllCCS	[M+HCOO]-	137.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-(4-Hydroxyphenyl)glycine	OC(=O)CNC1=CC=C(O)C=C1	2998.7	Standard polar	33892256
N-(4-Hydroxyphenyl)glycine	OC(=O)CNC1=CC=C(O)C=C1	1882.9	Standard non polar	33892256
N-(4-Hydroxyphenyl)glycine	OC(=O)CNC1=CC=C(O)C=C1	1849.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-(4-Hydroxyphenyl)glycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	1915.5	Semi standard non polar	33892256
N-(4-Hydroxyphenyl)glycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	1904.1	Standard non polar	33892256
N-(4-Hydroxyphenyl)glycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C1=CC=C(O[Si](C)(C)C)C=C1)[Si](C)(C)C	1922.0	Standard polar	33892256
N-(4-Hydroxyphenyl)glycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2611.3	Semi standard non polar	33892256
N-(4-Hydroxyphenyl)glycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2574.8	Standard non polar	33892256
N-(4-Hydroxyphenyl)glycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)[Si](C)(C)C(C)(C)C	2318.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-(4-Hydroxyphenyl)glycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1900000000-d7bbe716c1d942d1baf3	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(4-Hydroxyphenyl)glycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(4-Hydroxyphenyl)glycine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(4-Hydroxyphenyl)glycine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(4-Hydroxyphenyl)glycine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(4-Hydroxyphenyl)glycine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(4-Hydroxyphenyl)glycine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(4-Hydroxyphenyl)glycine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(4-Hydroxyphenyl)glycine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(4-Hydroxyphenyl)glycine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(4-Hydroxyphenyl)glycine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(4-Hydroxyphenyl)glycine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(4-Hydroxyphenyl)glycine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-(4-Hydroxyphenyl)glycine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

NMR Spectra

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

60494

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Glycin

METLIN ID

Not Available

PubChem Compound

67149

PDB ID

Not Available

ChEBI ID

55443

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-(4-Hydroxyphenyl)glycine (HMDB0255011)

MOL for HMDB0255011 (N-(4-Hydroxyphenyl)glycine)

3D MOL for HMDB0255011 (N-(4-Hydroxyphenyl)glycine)

3D SDF for HMDB0255011 (N-(4-Hydroxyphenyl)glycine)

3D-SDF for HMDB0255011 (N-(4-Hydroxyphenyl)glycine)

PDB for HMDB0255011 (N-(4-Hydroxyphenyl)glycine)

3D PDB for HMDB0255011 (N-(4-Hydroxyphenyl)glycine)

SMILES for HMDB0255011 (N-(4-Hydroxyphenyl)glycine)

INCHI for HMDB0255011 (N-(4-Hydroxyphenyl)glycine)

Structure for HMDB0255011 (N-(4-Hydroxyphenyl)glycine)

3D Structure for HMDB0255011 (N-(4-Hydroxyphenyl)glycine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

NMR Spectra