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Showing metabocard for Propionylglycine (HMDB0000783)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:10 UTC
HMDB IDHMDB0000783
Secondary Accession Numbers
  • HMDB00783
Metabolite Identification
Common NamePropionylglycine
DescriptionPropionylglycine 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-acylglycineThe level of propionylglycine is elevated in patients with propionic acidemia, which is an inherited deficiency of propionyl-CoA carboxylase. (Disorders of propionate and methylmalonate metabolism. In The Metabolic and Molecular Bases of Inherited Disease).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000783 (Propionylglycine)

Propyl alcohol.mol
  Mrv1652305271900272D          

  9  8  0  0  0  0            999 V2000
    1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.0313    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
  2  6  1  0  0  0  0
M  END
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3D MOL for HMDB0000783 (Propionylglycine)

HMDB0000783
     RDKit          3D
Propionylglycine
 18 17  0  0  0  0  0  0  0  0999 V2000
    2.8296   -0.0921    0.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8405   -0.6897   -0.4808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5371   -0.0116   -0.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4457    0.9103    0.5170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6094   -0.3710   -1.1043 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8635    0.3280   -0.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3559    0.1889    0.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6709   -0.4795    1.2793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5186    0.7609    0.8913 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8464   -0.1716   -0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8693   -0.6650    1.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5993    0.9905    0.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -1.7848   -0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1795   -0.5287   -1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5087   -1.1410   -1.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7241    1.3913   -1.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6315   -0.1299   -1.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0316    1.4949    0.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  9 18  1  0
M  END
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3D SDF for HMDB0000783 (Propionylglycine)

Propyl alcohol.mol
  Mrv1652305271900272D          

  9  8  0  0  0  0            999 V2000
    1.0717   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -1.0313    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
  2  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000783

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H9NO3/c1-2-4(7)6-3-5(8)9/h2-3H2,1H3,(H,6,7)(H,8,9)

> <INCHI_KEY>
WOMAZEJKVZLLFE-UHFFFAOYSA-N

> <FORMULA>
C5H9NO3

> <MOLECULAR_WEIGHT>
131.1299

> <EXACT_MASS>
131.058243159

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.599817604436712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-propanamidoacetic acid

> <ALOGPS_LOGP>
-0.44

> <JCHEM_LOGP>
-0.628093107

> <ALOGPS_LOGS>
-0.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.689212481256273

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.934994879966568

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9892232744887397

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
30.0741

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.34e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
propionylglycine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0000783 (Propionylglycine)

HMDB0000783
     RDKit          3D
Propionylglycine
 18 17  0  0  0  0  0  0  0  0999 V2000
    2.8296   -0.0921    0.4633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8405   -0.6897   -0.4808 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5371   -0.0116   -0.3275 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4457    0.9103    0.5170 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6094   -0.3710   -1.1043 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8635    0.3280   -0.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3559    0.1889    0.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6709   -0.4795    1.2793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5186    0.7609    0.8913 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8464   -0.1716   -0.0005 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8693   -0.6650    1.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5993    0.9905    0.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -1.7848   -0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1795   -0.5287   -1.5308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5087   -1.1410   -1.8005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7241    1.3913   -1.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6315   -0.1299   -1.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0316    1.4949    0.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  5 15  1  0
  6 16  1  0
  6 17  1  0
  9 18  1  0
M  END
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PDB for HMDB0000783 (Propionylglycine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Propyl alcohol.mol                                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.667  -0.385   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.667   0.385   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.001  -1.925   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.334   0.385   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.001   0.385   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.001   1.925   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.334  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.334  -1.925   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                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0000783 (Propionylglycine)

COMPND    HMDB0000783
HETATM    1  C1  UNL     1       2.830  -0.092   0.463  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.841  -0.690  -0.481  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.537  -0.012  -0.328  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.446   0.910   0.517  1.00  0.00           O  
HETATM    5  N1  UNL     1      -0.609  -0.371  -1.104  1.00  0.00           N  
HETATM    6  C4  UNL     1      -1.864   0.328  -0.913  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.356   0.189   0.474  1.00  0.00           C  
HETATM    8  O2  UNL     1      -1.671  -0.479   1.279  1.00  0.00           O  
HETATM    9  O3  UNL     1      -3.519   0.761   0.891  1.00  0.00           O  
HETATM   10  H1  UNL     1       3.846  -0.172  -0.000  1.00  0.00           H  
HETATM   11  H2  UNL     1       2.869  -0.665   1.405  1.00  0.00           H  
HETATM   12  H3  UNL     1       2.599   0.990   0.656  1.00  0.00           H  
HETATM   13  H4  UNL     1       1.767  -1.785  -0.318  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.180  -0.529  -1.531  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.509  -1.141  -1.800  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.724   1.391  -1.199  1.00  0.00           H  
HETATM   17  H8  UNL     1      -2.631  -0.130  -1.578  1.00  0.00           H  
HETATM   18  H9  UNL     1      -4.032   1.495   0.464  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3   13   14
CONECT    3    4    4    5
CONECT    5    6   15
CONECT    6    7   16   17
CONECT    7    8    8    9
CONECT    9   18
END
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SMILES for HMDB0000783 (Propionylglycine)

CCC(=O)NCC(O)=O
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INCHI for HMDB0000783 (Propionylglycine)

InChI=1S/C5H9NO3/c1-2-4(7)6-3-5(8)9/h2-3H2,1H3,(H,6,7)(H,8,9)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-Propanamidoacetic acidChEBI
N-Propionyl-glycineChEBI
N-PropionylglycineChEBI
Propanamidoacetic acidChEBI
PropanoylglycineChEBI
Propionylaminoacetic acidChEBI
2-PropanamidoacetateGenerator
PropanamidoacetateGenerator
PropionylaminoacetateGenerator
Chemical FormulaC5H9NO3
Average Molecular Weight131.1299
Monoisotopic Molecular Weight131.058243159
IUPAC Name2-propanamidoacetic acid
Traditional Namepropionylglycine
CAS Registry Number21709-90-0
SMILES
CCC(=O)NCC(O)=O
InChI Identifier
InChI=1S/C5H9NO3/c1-2-4(7)6-3-5(8)9/h2-3H2,1H3,(H,6,7)(H,8,9)
InChI KeyWOMAZEJKVZLLFE-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg126.92830932474
[M-H]-Not Available126.928http://allccs.zhulab.cn/database/detail?ID=AllCCS00000033
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022240
KNApSAcK IDNot Available
Chemspider ID89122
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5749
PubChem Compound98681
PDB IDNot Available
ChEBI ID89836
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKatz, J.; Lieberman, I.; Barker, H. A. Formation of propionyl-, butyryl-, and other acylglycines by enzymes of Clostridium kluyveri. Journal of Biological Chemistry (1953), 200 431-41.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bergstrom T, Greter J, Levin AH, Steen G, Tryding N, Wass U: Propionyl-CoA carboxylase deficiency: case report, effect of low-protein diet and identification of 3-oxo-2-methylvaleric acid 3-hydroxy-2-methylvaleric acid, and maleic acid in urine. Scand J Clin Lab Invest. 1981 Apr;41(2):117-26. [PubMed:7313494 ]
  2. Prasad C, Nurko S, Borovoy J, Korson MS: The importance of gut motility in the metabolic control of propionic acidemia. J Pediatr. 2004 Apr;144(4):532-5. [PubMed:15069406 ]
  3. (). Fenton, W.A., Gravel, R.A., Rosenblatt, D.S. Disorders of propionate and methylmalonate metabolism.. .
  4. (). Mayo Medical Laboratories 2005 Test Catalog. .

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