MiMeDB: Showing metabocard for Phenylpropionylglycine (MMDBc0000374)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:36:23 UTC

Update Date

2024-04-30 19:31:59 UTC

Metabolite ID

MMDBc0000374

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>
MMDBc0000374

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₁H₁₃NO₃

Average Mass

207.2258

Monoisotopic Mass

207.089543287

IUPAC Name

2-(3-phenylpropanamido)acetic acid

Traditional Name

phenylpropionylglycine

CAS Registry Number

Not Available

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

Functional Ontology

Physical Properties

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-6900000000-49e6bd1ae55ef730be57	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-03l3-7910000000-288e575c4d82667708e6	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-056r-9510000000-857882337db8707be6da	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-3900000000-ac64df3f4f25d003198b	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-056u-9400000000-ba5317e2dcb281f5ad7f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-5232244a5f1e32f44bfa	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-9120000000-3ad79b9ff64c3f9402d4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-952c82e2b34ef96383e8	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-5980000000-e671cd58f497ac7faac9	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-9600000000-f46c69e1694bd406aed7	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-9300000000-614fceaf9ffefb201233	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0390000000-aa434ae4ae70d3eae4bf	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-6970000000-55314833bc2ceca004c0	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-9200000000-26dcb24e7bc9b913dd22	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1690000000-8b2f04f031ae7c4b49e2	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-8910000000-18d0ad5b9e5aa8c4284c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-9100000000-9feb6c67f526b26df373	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4l-3920000000-f55c3c8e5ea50cbea724	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-8900000000-da57702d9fb756c9d7e3	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6u-9600000000-6de90f0cc8c6eaf079f4	2021-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)		2012-12-05	View Spectrum

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Urine	Detected and Quantified	3.819			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	HMDB	2380628
Human Urine	Detected and Quantified	12.00295			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	HMDB	2380628
Human Urine	Detected and Quantified	18.00442			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	HMDB	2380628
Human Urine	Detected and Quantified	20.732			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	HMDB	2380628
Human Urine	Detected and Quantified	32.735			umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Medium Chain Acyl-CoA Dehydrogenase Deficiency	HMDB	2380628
Human Urine	Detected and Quantified	0.03			umol/mmol creatinine	Adult (>18 years old)	Not Specified	Propionic acidemia	HMDB	28853722
Human Urine	Detected and Quantified	<0.0010‚Äì0.0656			umol/mmol creatinine	Adult (25-30 years old)	Both		HMDB	23062437
Human Urine	Detected and Quantified	<0.0010‚Äì0.0657			umol/mmol creatinine	Adult (25-30 years old)	Both		HMDB	23062437
Human Urine	Detected and Quantified	<0.13			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	28853722
Human Urine	Detected and Quantified	0.0020‚Äì0.0573			umol/mmol creatinine	Adult (25-30 years old)	Both		HMDB	23062437
Human Urine	Detected and Quantified	0.01	0	0-42	umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	HMDB	21704015
Human Urine	Detected and Quantified	1.00	0.00	2.00	umol/mmol creatinine	Adult (>18 years old)	Both	Medium Chain Acyl-CoA Dehydrogenase Deficiency	HMDB	MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de)
Human Urine	Detected and Quantified	0			umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	HMDB	BC Children's Hospital Biochemical Genetics Lab
Human Urine	Detected but not Quantified					Adult (24-38years old)	Not Specified	Normal	HMDB	20971021
Human Feces	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified					Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

References

Showing metabocard for Phenylpropionylglycine (MMDBc0000374)

MOL for #<Metabolite:0x00007fb7ecac4f58>

3D MOL for #<Metabolite:0x00007fb7ecac4f58>

3D SDF for #<Metabolite:0x00007fb7ecac4f58>

3D-SDF for #<Metabolite:0x00007fb7ecac4f58>

PDB for #<Metabolite:0x00007fb7ecac4f58>

3D PDB for #<Metabolite:0x00007fb7ecac4f58>

SMILES for #<Metabolite:0x00007fb7ecac4f58>

INCHI for #<Metabolite:0x00007fb7ecac4f58>

Structure for #<Metabolite:0x00007fb7ecac4f58>

3D Structure for #<Metabolite:0x00007fb7ecac4f58>