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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:12 UTC

HMDB ID

HMDB0000821

Secondary Accession Numbers

HMDB00821

Metabolite Identification

Common Name

Phenylacetylglycine

Description

Phenylacetylglycine is an acyl glycine. Acyl glycines are normally minor metabolites of fatty acids. However, the excretion of certain acyl glycines is increased in several inborn errors of metabolism. In certain cases the measurement of these metabolites in body fluids can be used to diagnose disorders associated with mitochondrial fatty acid beta-oxidation. Acyl glycines are produced through the action of glycine N-acyltransferase (EC 2.3.1.13) which is an enzyme that catalyzes the chemical reaction:. acyl-CoA + glycine < -- > CoA + N-acylglycine. Phenylacetylglycine or PAG is a glycine conjugate of phenylacetic acid. Phenylacetic acid may arise from exposure to styrene (plastic) or through the consumption of fruits and vegetables. Phenylacetic acid is used in some perfumes, possessing a honey-like odour in low concentrations, and is also used in penicillin G production. PAG is a putative biomarker of phospholipidosis. Urinary PAG is elevated in animals exhibiting abnormal phospholipid accumulation in many tissues and may thus be useful as a surrogate biomarker for phospholipidosis. (PMID: 15764292 ) The presence of phenylacetylglycine in urine has been confirmed for dogs, rats and mice. However, the presence of this compound in human urine is controversial. GC-MS studies have not found this compound (PMID: 7492634 ) while NMR studies claimed to have identified it (PMID: 21167146 ). It appears that phenylacetylglycine may sometimes be mistaken for phenylacetylglutamine via NMR.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Phenylacetylglycine.mol
  Mrv1652305271900262D          

 14 14  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 N   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
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   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 O   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
    1.4289    0.0000    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  2  0  0  0  0
  8  9  1  0  0  0  0
  2  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000821

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CNC(=O)CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO3/c12-9(11-7-10(13)14)6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14)

> <INCHI_KEY>
UTYVDVLMYQPLQB-UHFFFAOYSA-N

> <FORMULA>
C10H11NO3

> <MOLECULAR_WEIGHT>
193.1992

> <EXACT_MASS>
193.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.085212338243267

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-phenylacetamido)acetic acid

> <ALOGPS_LOGP>
0.51

> <JCHEM_LOGP>
0.5057108656666667

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.646653717913555

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.985264151206934

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9261944657280297

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
50.169100000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylacetylglycine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Phenylacetylglycine.mol                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.334  -0.770   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1    3    4    5                                                  
CONECT    2    3    6                                                       
CONECT    3    2    1                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    7    8    2                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9   10   14    8                                                  
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 Stereo Labels

Synonyms

Value	Source
N-Phenacetylglycine	ChEBI
N-Phenylacetylglycine	ChEBI
Phenaceturic acid	ChEBI
Phenacetylglycine	ChEBI
Phenacetate	Generator
Phenacetic acid	Generator
((Phenylacetyl)amino)acetic acid	HMDB
N-(Phenylacetyl)-glycine	HMDB
N-(Phenylacetyl)glycine	HMDB
PAA	HMDB
PAG	HMDB
Phenaceturate	HMDB
Phenylacetyl glycine	HMDB
[(Phenylacetyl)amino]acetate	HMDB
[(Phenylacetyl)amino]acetic acid	HMDB
Phenylacetylglycine	MeSH

Chemical Formula

C₁₀H₁₁NO₃

Average Molecular Weight

193.1992

Monoisotopic Molecular Weight

193.073893223

IUPAC Name

2-(2-phenylacetamido)acetic acid

Traditional Name

phenylacetylglycine

CAS Registry Number

500-98-1

SMILES

OC(=O)CNC(=O)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C10H11NO3/c12-9(11-7-10(13)14)6-8-4-2-1-3-5-8/h1-5H,6-7H2,(H,11,12)(H,13,14)

InChI Key

UTYVDVLMYQPLQB-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
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

monocarboxylic acid (CHEBI:27480 )
monocarboxylic acid amide (CHEBI:27480 )
N-acylglycine (CHEBI:27480 )

Ontology

Physiological effect

Health effect

Circulatory system disorder

Cardiac disorder

Heart failure (HMDB: HMDB0000821)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (HMDB: HMDB0000821)
Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0000821)

Source

Endogenous

Endogenous (HMDB: HMDB0000821)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Meats (HMDB: HMDB0000821)
Legumes (HMDB: HMDB0000821)

Cereal and cereal product

Cereal product

Whole grain cereal products (HMDB: HMDB0000821)

Nut

Nuts (HMDB: HMDB0000821)

Milk and milk product

Dairy products (HMDB: HMDB0000821)

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Egg

Eggs (HMDB: HMDB0000821)

Soy

Soy (HMDB: HMDB0000821)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	7.3 mg/mL at 11 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	147.227	30932474
[M-H]-	Not Available	147.227	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000035

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.66 g/L	ALOGPS
logP	0.51	ALOGPS
logP	0.51	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.99	ChemAxon
pKa (Strongest Basic)	-2.9	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	4	ChemAxon
Refractivity	50.17 m³·mol⁻¹	ChemAxon
Polarizability	19.09 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
DarkChem	[M+H]+	144.419	31661259
DarkChem	[M-H]-	141.375	31661259
AllCCS	[M+H]+	141.582	32859911
AllCCS	[M-H]-	142.634	32859911
DeepCCS	[M+H]+	137.711	30932474
DeepCCS	[M-H]-	135.167	30932474
DeepCCS	[M-2H]-	170.839	30932474
DeepCCS	[M+Na]+	145.917	30932474
AllCCS	[M+H]+	141.6	32859911
AllCCS	[M+H-H2O]+	137.5	32859911
AllCCS	[M+NH4]+	145.4	32859911
AllCCS	[M+Na]+	146.4	32859911
AllCCS	[M-H]-	142.6	32859911
AllCCS	[M+Na-2H]-	143.3	32859911
AllCCS	[M+HCOO]-	144.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenylacetylglycine	OC(=O)CNC(=O)CC1=CC=CC=C1	3035.9	Standard polar	33892256
Phenylacetylglycine	OC(=O)CNC(=O)CC1=CC=CC=C1	1633.0	Standard non polar	33892256
Phenylacetylglycine	OC(=O)CNC(=O)CC1=CC=CC=C1	1898.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenylacetylglycine,1TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)CC1=CC=CC=C1	1906.9	Semi standard non polar	33892256
Phenylacetylglycine,1TMS,isomer #2	C[Si](C)(C)N(CC(=O)O)C(=O)CC1=CC=CC=C1	1873.5	Semi standard non polar	33892256
Phenylacetylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	1854.8	Semi standard non polar	33892256
Phenylacetylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	1904.6	Standard non polar	33892256
Phenylacetylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=CC=C1)[Si](C)(C)C	2227.5	Standard polar	33892256
Phenylacetylglycine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)CC1=CC=CC=C1	2155.5	Semi standard non polar	33892256
Phenylacetylglycine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)CC1=CC=CC=C1	2093.8	Semi standard non polar	33892256
Phenylacetylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2344.2	Semi standard non polar	33892256
Phenylacetylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2327.5	Standard non polar	33892256
Phenylacetylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2464.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Phenylacetylglycine EI-B (Non-derivatized)	splash10-0006-9000000000-96f6d1819364e0910beb	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylacetylglycine GC-EI-TOF (Non-derivatized)	splash10-0udl-5930000000-6e0622de46a05b80d685	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylacetylglycine GC-EI-TOF (Non-derivatized)	splash10-0006-9610000000-b8948d031afc0e4b8f78	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylacetylglycine EI-B (Non-derivatized)	splash10-0006-9000000000-96f6d1819364e0910beb	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylacetylglycine GC-EI-TOF (Non-derivatized)	splash10-0udl-5930000000-6e0622de46a05b80d685	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylacetylglycine GC-EI-TOF (Non-derivatized)	splash10-0006-9610000000-b8948d031afc0e4b8f78	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylacetylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9500000000-50b56f103c1a79f65878	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylacetylglycine GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9200000000-5d39e42ac2b4d7b6f726	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylacetylglycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylacetylglycine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylacetylglycine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylacetylglycine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglycine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-004l-9100000000-134ddfbf19f2ee4e9260	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglycine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0006-9000000000-9656d3b4670efd4db2e3	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglycine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0006-9000000000-9cf5ff47848cf5bf99b2	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglycine EI-B (VARIAN MAT-44) , Positive-QTOF	splash10-0006-9000000000-f37d59edacbcf679b420	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglycine 20V, Positive-QTOF	splash10-0006-9200000000-92c7f1e2376eb0e84b36	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglycine 10V, Positive-QTOF	splash10-002f-9200000000-c48677787f705755d93f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglycine 30V, Positive-QTOF	splash10-0006-9300000000-dd5f78904d0d0dacb641	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglycine 40V, Positive-QTOF	splash10-0006-9300000000-1acb6b8d75e7381ccbde	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglycine 30V, Positive-QTOF	splash10-0596-9100000000-415a6a1ccc4a5a25ad4f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglycine 10V, Positive-QTOF	splash10-002f-9100000000-52063d451d15512ae652	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglycine 35V, Positive-QTOF	splash10-0006-9000000000-b4cfc8b9dad7406c720f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglycine 0V, Positive-QTOF	splash10-002f-9000000000-88eadbe8bb1b30f341b0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglycine 40V, Negative-QTOF	splash10-00di-9000000000-abf76489fbf1b18e56aa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglycine 30V, Negative-QTOF	splash10-00di-9000000000-1168dca79ce76e8ff744	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglycine 10V, Negative-QTOF	splash10-00di-9000000000-709de7804cd48ddac3b5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglycine 35V, Negative-QTOF	splash10-00di-9000000000-668624127e5eb3cd947a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylacetylglycine 20V, Negative-QTOF	splash10-00di-9000000000-f0284ab582fc7a2b28c4	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylacetylglycine 10V, Positive-QTOF	splash10-00dl-9600000000-96499e21a08e5d190040	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylacetylglycine 20V, Positive-QTOF	splash10-00fr-9200000000-aeac60944271030f9751	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylacetylglycine 40V, Positive-QTOF	splash10-00bc-9000000000-4caba04f2e229a8013b4	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylacetylglycine 10V, Negative-QTOF	splash10-0006-0900000000-899f25422883181dbe57	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylacetylglycine 20V, Negative-QTOF	splash10-006x-4900000000-433c13250fe2463708f4	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylacetylglycine 40V, Negative-QTOF	splash10-006x-9200000000-0b6ae74cd7a7ddce62d7	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylacetylglycine 10V, Negative-QTOF	splash10-00di-9000000000-e21745e55a3af36629b3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylacetylglycine 20V, Negative-QTOF	splash10-00di-9000000000-078d0d5a533b72168681	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Saliva
Urine

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	Adult (>18 years old)	Both	Normal	32966057	details
Saliva	Detected and Quantified	19.55 +/- 7.98 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	0.0366–0.1361 umol/mmol creatinine	Adult (25-30 years old)	Both	Not Available	23062437	details
Urine	Detected and Quantified	0.0394–0.1695 umol/mmol creatinine	Adult (25-30 years old)	Both	Not Available	23062437	details
Urine	Detected and Quantified	0.0370–0.1314 umol/mmol creatinine	Adult (25-30 years old)	Both	Not Available	23062437	details
Urine	Detected and Quantified	65 +/- 15 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	21167146	details
Urine	Detected but not Quantified	Not Quantified	Adult (24-38years old)	Not Specified	Normal	20971021	details
Urine	Detected and Quantified	74.841 +/- 30.788 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	21389975	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22932811	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	100 +/- 60 umol/mmol creatinine	Adult (>18 years old)	Both	Heart failure	21167146	details
Urine	Detected and Quantified	61.775 +/- 51.294 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details

Associated Disorders and Diseases

Disease References

Heart failure
Kang SM, Park JC, Shin MJ, Lee H, Oh J, Ryu DH, Hwang GS, Chung JH: (1)H nuclear magnetic resonance based metabolic urinary profiling of patients with ischemic heart failure. Clin Biochem. 2011 Mar;44(4):293-9. doi: 10.1016/j.clinbiochem.2010.11.010. Epub 2010 Dec 15. [PubMed:21167146 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022266

KNApSAcK ID

Not Available

Chemspider ID

61452

KEGG Compound ID

C05598

BioCyc ID

CPD-11715

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

4237

PubChem Compound

68144

PDB ID

Not Available

ChEBI ID

27480

Food Biomarker Ontology

Not Available

VMH ID

M02723

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Ford, Jared H. Convenient synthesis of phenaceturic acid. Journal of the American Chemical Society (1949), 71 3842.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Wang Y, Holmes E, Nicholson JK, Cloarec O, Chollet J, Tanner M, Singer BH, Utzinger J: Metabonomic investigations in mice infected with Schistosoma mansoni: an approach for biomarker identification. Proc Natl Acad Sci U S A. 2004 Aug 24;101(34):12676-81. Epub 2004 Aug 16. [PubMed:15314235 ]
Ito T, Kidouchi K, Sugiyama N, Kajita M, Chiba T, Niwa T, Wada Y: Liquid chromatographic-atmospheric pressure chemical ionization mass spectrometric analysis of glycine conjugates and urinary isovalerylglycine in isovaleric acidemia. J Chromatogr B Biomed Appl. 1995 Aug 18;670(2):317-22. [PubMed:8548022 ]
Matsumoto M, Zhang CH, Kosugi C, Matsumoto I: Gas chromatography-mass spectrometric studies of canine urinary metabolism. J Vet Med Sci. 1995 Apr;57(2):205-11. [PubMed:7492634 ]
Kang SM, Park JC, Shin MJ, Lee H, Oh J, Ryu DH, Hwang GS, Chung JH: (1)H nuclear magnetic resonance based metabolic urinary profiling of patients with ischemic heart failure. Clin Biochem. 2011 Mar;44(4):293-9. doi: 10.1016/j.clinbiochem.2010.11.010. Epub 2010 Dec 15. [PubMed:21167146 ]
Delaney J, Neville WA, Swain A, Miles A, Leonard MS, Waterfield CJ: Phenylacetylglycine, a putative biomarker of phospholipidosis: its origins and relevance to phospholipid accumulation using amiodarone treated rats as a model. Biomarkers. 2004 May-Jun;9(3):271-90. [PubMed:15764292 ]

Enzymes

Enzyme Details

1. Glycine N-acyltransferase

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:: GLYAT
Uniprot ID:: Q6IB77
Molecular weight:: 18506.33

Reactions

Phenylacetyl-CoA + Glycine → Phenylacetylglycine + Coenzyme A	details

Enzyme Details

2. Glycine N-acyltransferase-like protein 1

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Acyltransferase which transfers an acyl group to the N-terminus of glutamine. Can use phenylacetyl-CoA as an acyl donor.
Gene Name:: GLYATL1
Uniprot ID:: Q969I3
Molecular weight:: 35100.895

Enzyme Details

3. Glycine N-acyltransferase-like protein 2

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers the acyl group to the N-terminus of glycine. Conjugates numerous substrates, such as arachidonoyl-CoA and saturated medium and long-chain acyl-CoAs ranging from chain-length C8:0-CoA to C18:0-CoA, to form a variety of N-acylglycines. Shows a preference for monounsaturated fatty acid oleoyl-CoA (C18:1-CoA) as an acyl donor. Does not exhibit any activity toward C22:6-CoA and chenodeoxycholoyl-CoA, nor toward serine or alanine.
Gene Name:: GLYATL2
Uniprot ID:: Q8WU03
Molecular weight:: 34277.055

Enzyme Details

4. Glycine N-acyltransferase-like protein 3

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Acyltransferase which transfers the acyl group to the N- terminus of glycine
Gene Name:: GLYATL3
Uniprot ID:: Q5SZD4
Molecular weight:: 32703.3

Enzyme Details

5. N-acetyltransferase ESCO1

General function:: Involved in damaged DNA binding
Specific function:: Acetyltransferase required for the establishment of sister chromatid cohesion and couple the processes of cohesion and DNA replication to ensure that only sister chromatids become paired together. In contrast to the structural cohesins, the deposition and establishment factors are required only during S phase. Acts by mediating the acetylation of cohesin component SMC3
Gene Name:: ESCO1
Uniprot ID:: Q5FWF5
Molecular weight:: 94982.2

Showing metabocard for Phenylacetylglycine (HMDB0000821)

MOL for HMDB0000821 (Phenylacetylglycine)

3D MOL for HMDB0000821 (Phenylacetylglycine)

3D SDF for HMDB0000821 (Phenylacetylglycine)

3D-SDF for HMDB0000821 (Phenylacetylglycine)

PDB for HMDB0000821 (Phenylacetylglycine)

3D PDB for HMDB0000821 (Phenylacetylglycine)

SMILES for HMDB0000821 (Phenylacetylglycine)

INCHI for HMDB0000821 (Phenylacetylglycine)

Structure for HMDB0000821 (Phenylacetylglycine)

3D Structure for HMDB0000821 (Phenylacetylglycine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions