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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 17:15:15 UTC

HMDB ID

HMDB0000860

Secondary Accession Numbers

HMDB00860

Metabolite Identification

Common Name

Phenylpropionylglycine

Description

Phenylpropionylglycine 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. The detection of phenylpropionylglycine in urine after an oral load of phenylpropionic acid can be used to diagnose deficiency of medium-chain acyl-CoA dehydrogenase, a frequent and treatable metabolic defect. (PMID 9234867 ).

Structure

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

Phenylpyruvic acid.mol
  Mrv1652305271900262D          

 15 15  0  0  0  0            999 V2000
    2.5006    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.8250    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
  8  9  1  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
 14 15  1  0  0  0  0
 10 15  2  0  0  0  0
  9 10  1  0  0  0  0
  2  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000860

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CNC(=O)CCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H13NO3/c13-10(12-8-11(14)15)7-6-9-4-2-1-3-5-9/h1-5H,6-8H2,(H,12,13)(H,14,15)

> <INCHI_KEY>
YEIQSAXUPKPPBN-UHFFFAOYSA-N

> <FORMULA>
C11H13NO3

> <MOLECULAR_WEIGHT>
207.2258

> <EXACT_MASS>
207.089543287

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.46582134497297

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3-phenylpropanamido)acetic acid

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
0.9502795306666662

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.812773595108002

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.002244913986784

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0648535972093636

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
54.77010000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.52e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylpropionylglycine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Phenylpyruvic acid.mol                            
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       4.668   0.000   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.001   0.000   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.668   1.540   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.002  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.667  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.667  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.334   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.002   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.002   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.334   1.540   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    8   10                                                       
CONECT   10   11   15    9                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0000860
HETATM    1  O1  UNL     1       3.617   0.446   1.382  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.392   0.559   0.422  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.735   0.314   0.594  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.890   0.955  -0.908  1.00  0.00           C  
HETATM    5  N1  UNL     1       2.460   1.151  -0.832  1.00  0.00           N  
HETATM    6  C3  UNL     1       1.618   0.093  -0.450  1.00  0.00           C  
HETATM    7  O3  UNL     1       2.083  -1.024  -0.173  1.00  0.00           O  
HETATM    8  C4  UNL     1       0.166   0.303  -0.375  1.00  0.00           C  
HETATM    9  C5  UNL     1      -0.547  -0.961   0.054  1.00  0.00           C  
HETATM   10  C6  UNL     1      -2.017  -0.759   0.133  1.00  0.00           C  
HETATM   11  C7  UNL     1      -2.589  -0.335   1.319  1.00  0.00           C  
HETATM   12  C8  UNL     1      -3.950  -0.127   1.461  1.00  0.00           C  
HETATM   13  C9  UNL     1      -4.742  -0.362   0.350  1.00  0.00           C  
HETATM   14  C10 UNL     1      -4.180  -0.785  -0.838  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.823  -0.989  -0.968  1.00  0.00           C  
HETATM   16  H1  UNL     1       6.297   1.099   0.959  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.393   1.886  -1.285  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.152   0.175  -1.684  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.072   2.104  -1.069  1.00  0.00           H  
HETATM   20  H5  UNL     1      -0.180   0.572  -1.402  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.016   1.142   0.329  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.111  -1.315   0.997  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.381  -1.714  -0.754  1.00  0.00           H  
HETATM   24  H9  UNL     1      -1.962  -0.153   2.184  1.00  0.00           H  
HETATM   25  H10 UNL     1      -4.381   0.208   2.408  1.00  0.00           H  
HETATM   26  H11 UNL     1      -5.812  -0.199   0.460  1.00  0.00           H  
HETATM   27  H12 UNL     1      -4.819  -0.962  -1.693  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.367  -1.320  -1.892  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   16
CONECT    4    5   17   18
CONECT    5    6   19
CONECT    6    7    7    8
CONECT    8    9   20   21
CONECT    9   10   22   23
CONECT   10   11   11   15
CONECT   11   12   24
CONECT   12   13   13   25
CONECT   13   14   26
CONECT   14   15   15   27
CONECT   15   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-[(1-Hydroxy-3-phenylpropylidene)amino]acetate	HMDB
(3-Phenyl-propionylamino)-acetate	HMDB
(3-Phenyl-propionylamino)-acetic acid	HMDB
(3-Phenylpropionyl)glycine	HMDB
N-(3-Phenyl-propionyl)-glycine	HMDB
N-(3-Phenylpropanoyl)glycine	HMDB
3-Phenylpropionylglycine	HMDB

Chemical Formula

C₁₁H₁₃NO₃

Average Molecular Weight

207.2258

Monoisotopic Molecular Weight

207.089543287

IUPAC Name

2-(3-phenylpropanamido)acetic acid

Traditional Name

phenylpropionylglycine

CAS Registry Number

56613-60-6

SMILES

OC(=O)CNC(=O)CCC1=CC=CC=C1

InChI Identifier

InChI=1S/C11H13NO3/c13-10(12-8-11(14)15)7-6-9-4-2-1-3-5-9/h1-5H,6-8H2,(H,12,13)(H,14,15)

InChI Key

YEIQSAXUPKPPBN-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
Fatty amide
Fatty acyl
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
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

Not Available

Ontology

Physiological effect

Health effect

Genetic disorder

Inborn errors of metabolism

Medium Chain Acyl-CoA Dehydrogenase Deficiency (HMDB: HMDB0000860)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 23062437)
Feces (PMID: 29808030)

Source

Endogenous

Endogenous (HMDB: HMDB0000860)

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)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

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)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Medium Chain Acyl Co A Dehydrogenase Deficiency (MarkerDB: MDB00029990)
Propionic acidemia (MarkerDB: MDB00029990)

Physical Properties

State

Solid

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	153.297	30932474
[M-H]-	Not Available	153.297	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000036
[M+H]+	Not Available	149.466	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000036

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.25 g/L	ALOGPS
logP	0.93	ALOGPS
logP	0.95	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4	ChemAxon
pKa (Strongest Basic)	-2.1	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	5	ChemAxon
Refractivity	54.77 m³·mol⁻¹	ChemAxon
Polarizability	21.47 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]+	146.987	31661259
DarkChem	[M-H]-	145.455	31661259
AllCCS	[M+H]+	145.409	32859911
AllCCS	[M-H]-	147.795	32859911
DeepCCS	[M+H]+	141.683	30932474
DeepCCS	[M-H]-	139.287	30932474
DeepCCS	[M-2H]-	174.293	30932474
DeepCCS	[M+Na]+	148.784	30932474
AllCCS	[M+H]+	145.4	32859911
AllCCS	[M+H-H2O]+	141.5	32859911
AllCCS	[M+NH4]+	149.0	32859911
AllCCS	[M+Na]+	150.1	32859911
AllCCS	[M-H]-	147.8	32859911
AllCCS	[M+Na-2H]-	148.3	32859911
AllCCS	[M+HCOO]-	149.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenylpropionylglycine	OC(=O)CNC(=O)CCC1=CC=CC=C1	3191.0	Standard polar	33892256
Phenylpropionylglycine	OC(=O)CNC(=O)CCC1=CC=CC=C1	1658.0	Standard non polar	33892256
Phenylpropionylglycine	OC(=O)CNC(=O)CCC1=CC=CC=C1	2005.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenylpropionylglycine,1TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)CCC1=CC=CC=C1	2024.8	Semi standard non polar	33892256
Phenylpropionylglycine,1TMS,isomer #2	C[Si](C)(C)N(CC(=O)O)C(=O)CCC1=CC=CC=C1	1994.5	Semi standard non polar	33892256
Phenylpropionylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)CCC1=CC=CC=C1)[Si](C)(C)C	1976.7	Semi standard non polar	33892256
Phenylpropionylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)CCC1=CC=CC=C1)[Si](C)(C)C	1997.8	Standard non polar	33892256
Phenylpropionylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)CCC1=CC=CC=C1)[Si](C)(C)C	2326.8	Standard polar	33892256
Phenylpropionylglycine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)CCC1=CC=CC=C1	2271.5	Semi standard non polar	33892256
Phenylpropionylglycine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)CCC1=CC=CC=C1	2215.3	Semi standard non polar	33892256
Phenylpropionylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2460.8	Semi standard non polar	33892256
Phenylpropionylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2436.7	Standard non polar	33892256
Phenylpropionylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CCC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2561.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylpropionylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-6900000000-49e6bd1ae55ef730be57	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylpropionylglycine GC-MS (1 TMS) - 70eV, Positive	splash10-03l3-7910000000-288e575c4d82667708e6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylpropionylglycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylpropionylglycine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylpropionylglycine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylpropionylglycine 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 - Phenylpropionylglycine Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-056r-9510000000-857882337db8707be6da	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylpropionylglycine Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0a4i-3900000000-ac64df3f4f25d003198b	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylpropionylglycine Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-056u-9400000000-ba5317e2dcb281f5ad7f	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylpropionylglycine 20V, Negative-QTOF	splash10-00di-9000000000-5232244a5f1e32f44bfa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylpropionylglycine 10V, Negative-QTOF	splash10-00di-9120000000-3ad79b9ff64c3f9402d4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylpropionylglycine 40V, Negative-QTOF	splash10-00di-9000000000-952c82e2b34ef96383e8	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropionylglycine 10V, Positive-QTOF	splash10-0a4i-5980000000-e671cd58f497ac7faac9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropionylglycine 20V, Positive-QTOF	splash10-0a6r-9600000000-f46c69e1694bd406aed7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropionylglycine 40V, Positive-QTOF	splash10-0a6r-9300000000-614fceaf9ffefb201233	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropionylglycine 10V, Negative-QTOF	splash10-0a4i-0390000000-aa434ae4ae70d3eae4bf	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropionylglycine 20V, Negative-QTOF	splash10-0ab9-6970000000-55314833bc2ceca004c0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropionylglycine 40V, Negative-QTOF	splash10-0ab9-9200000000-26dcb24e7bc9b913dd22	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropionylglycine 10V, Negative-QTOF	splash10-0a4i-1690000000-8b2f04f031ae7c4b49e2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropionylglycine 20V, Negative-QTOF	splash10-0a4l-8910000000-18d0ad5b9e5aa8c4284c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropionylglycine 40V, Negative-QTOF	splash10-004l-9100000000-9feb6c67f526b26df373	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropionylglycine 10V, Positive-QTOF	splash10-0a4l-3920000000-f55c3c8e5ea50cbea724	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropionylglycine 20V, Positive-QTOF	splash10-0a4l-8900000000-da57702d9fb756c9d7e3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylpropionylglycine 40V, Positive-QTOF	splash10-0a6u-9600000000-6de90f0cc8c6eaf079f4	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI+, Adduct: [M+Na]+)	2022-02-11	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)	2022-02-11	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+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
Feces
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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Urine	Detected and Quantified	<0.0010–0.0656 umol/mmol creatinine	Adult (25-30 years old)	Both	Not Available	23062437	details
Urine	Detected and Quantified	<0.0010–0.0657 umol/mmol creatinine	Adult (25-30 years old)	Both	Not Available	23062437	details
Urine	Detected and Quantified	0.0020–0.0573 umol/mmol creatinine	Adult (25-30 years old)	Both	Not Available	23062437	details
Urine	Detected but not Quantified	Not Quantified	Adult (24-38years old)	Not Specified	Normal	20971021	details
Urine	Detected and Quantified	0.01 (0-0-42) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	21704015	details
Urine	Detected and Quantified	<0.13 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	28853722	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.0 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected and Quantified	1.00 (0.00-2.00) umol/mmol creatinine	Adult (>18 years old)	Both	Medium Chain Acyl-CoA Dehydrogenase Deficiency	MetaGene: Metabol...	details
Urine	Detected and Quantified	0.03 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Propionic acidemia	28853722	details
Urine	Detected and Quantified	3.819 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	12.00295 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	18.00442 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	20.732 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details
Urine	Detected and Quantified	32.735 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	2380628	details

Associated Disorders and Diseases

Disease References

Medium Chain Acyl-CoA Dehydrogenase Deficiency
Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71. [PubMed:2380628 ] G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Propionic acidemia
Riemersma M, Hazebroek MR, Helderman-van den Enden ATJM, Salomons GS, Ferdinandusse S, Brouwers MCGJ, van der Ploeg L, Heymans S, Glatz JFC, van den Wijngaard A, Krapels IPC, Bierau J, Brunner HG: Propionic acidemia as a cause of adult-onset dilated cardiomyopathy. Eur J Hum Genet. 2017 Nov;25(11):1195-1201. doi: 10.1038/ejhg.2017.127. Epub 2017 Aug 30. [PubMed:28853722 ]

Associated OMIM IDs

201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
606054 (Propionic acidemia)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022286

KNApSAcK ID

Not Available

Chemspider ID

134261

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5823

PubChem Compound

152323

PDB ID

Not Available

ChEBI ID

266653

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00029990

Good Scents ID

Not Available

References

Synthesis Reference

Geurts, Muriel; Poupaert, Jacques H.; Scriba, Gerhard K. E.; Lambert, Didier M. N-(Benzyloxycarbonyl)glycine Esters and Amides as New Anticonvulsants. Journal of Medicinal Chemistry (1998), 41(1), 24-30.

Material Safety Data Sheet (MSDS)

Not Available

General References

Green A, Preece MA, de Sousa C, Pollitt RJ: Possible deleterious effect of L-carnitine supplementation in a patient with mild multiple acyl-CoA dehydrogenation deficiency (ethylmalonic-adipic aciduria). J Inherit Metab Dis. 1991;14(5):691-7. [PubMed:1779616 ]
Rocchiccioli F, Cartier PH, Bougneres PF: Mass spectrometric identification of abnormal aromatic compounds in the urine of a child with Reye's like syndrome. Biomed Mass Spectrom. 1984 Mar;11(3):127-31. [PubMed:6722284 ]
Flath B, Rolinski B, Roscher AA: Simple high-performance liquid chromatographic method for the detection of phenylpropionylglycine in urine as a diagnostic tool in inherited medium-chain acyl-coenzyme A dehydrogenase deficiency. J Chromatogr B Biomed Sci Appl. 1997 Jun 20;694(1):227-32. [PubMed:9234867 ]
Gregersen N, Winter V, Lyonnet S, Saudubray JM, Wendel U, Jensen TG, Andresen BS, Kolvraa S, Lehnert W, Bolund L, et al.: Molecular genetic characterization and urinary excretion pattern of metabolites in two families with MCAD deficiency due to compound heterozygosity with a 13 base pair insertion in one allele. J Inherit Metab Dis. 1994;17(2):169-84. [PubMed:7967471 ]
Rinaldo P, O'Shea JJ, Coates PM, Hale DE, Stanley CA, Tanaka K: Medium-chain acyl-CoA dehydrogenase deficiency. Diagnosis by stable-isotope dilution measurement of urinary n-hexanoylglycine and 3-phenylpropionylglycine. N Engl J Med. 1988 Nov 17;319(20):1308-13. [PubMed:3054550 ]
Penzien JM, Molz G, Wiesmann UN, Colombo JP, Buhlmann R, Wermuth B: Medium-chain acyl-CoA dehydrogenase deficiency does not correlate with apparent life-threatening events and the sudden infant death syndrome: results from phenylpropionate loading tests and DNA analysis. Eur J Pediatr. 1994 May;153(5):352-7. [PubMed:8033926 ]

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

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

Showing metabocard for Phenylpropionylglycine (HMDB0000860)

MOL for HMDB0000860 (Phenylpropionylglycine)

3D MOL for HMDB0000860 (Phenylpropionylglycine)

3D SDF for HMDB0000860 (Phenylpropionylglycine)

3D-SDF for HMDB0000860 (Phenylpropionylglycine)

PDB for HMDB0000860 (Phenylpropionylglycine)

3D PDB for HMDB0000860 (Phenylpropionylglycine)

SMILES for HMDB0000860 (Phenylpropionylglycine)

INCHI for HMDB0000860 (Phenylpropionylglycine)

Structure for HMDB0000860 (Phenylpropionylglycine)

3D Structure for HMDB0000860 (Phenylpropionylglycine)

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