Np mrd loader

Showing NP-Card for Propionylglycine (NP0001449)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:23:36 UTC
NP-MRD IDNP0001449
Secondary Accession NumbersNone
Natural Product 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
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001449 (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
Download

3D MOL for NP0001449 (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
Download

3D SDF for NP0001449 (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>
NP0001449

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0001449 (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
Download

PDB for NP0001449 (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
Download

3D PDB for NP0001449 (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
Download

SMILES for NP0001449 (Propionylglycine)

CCC(=O)NCC(O)=O
Download

INCHI for NP0001449 (Propionylglycine)

InChI=1S/C5H9NO3/c1-2-4(7)6-3-5(8)9/h2-3H2,1H3,(H,6,7)(H,8,9)
Download
View in JSmol
Synonyms
ValueSource
2-Propanamidoacetic acidChEBI
N-Propionyl-glycineChEBI
N-PropionylglycineChEBI
Propanamidoacetic acidChEBI
PropanoylglycineChEBI
Propionylaminoacetic acidChEBI
2-PropanamidoacetateGenerator
PropanamidoacetateGenerator
PropionylaminoacetateGenerator
Chemical FormulaC5H9NO3
Average Mass131.1299 Da
Monoisotopic Mass131.05824 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility33.4 g/LALOGPS
logP-0.44ALOGPS
logP-0.63ChemAxon
logS-0.59ALOGPS
pKa (Strongest Acidic)3.93ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity30.07 m³·mol⁻¹ChemAxon
Polarizability12.6 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000783
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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. Rasmussen K, Ando T, Nyhan WL, Hull D, Cottom D, Donnell G, Wadlington W, Kilroy AW: Excretion of propionylglycine in propionic acidaemia. Clin Sci. 1972 Jun;42(6):665-71. doi: 10.1042/cs0420665. [PubMed:5033805 ]
  4. Kido J, Matsumoto S, Nakamura K: Carglumic Acid Contributes to a Favorable Clinical Course in a Case of Severe Propionic Acidemia. Case Rep Pediatr. 2020 Mar 9;2020:4709548. doi: 10.1155/2020/4709548. eCollection 2020. [PubMed:32231837 ]
  5. Fisher L, Davies C, Al-Dirbashi OY, Ten Brink HJ, Chakraborty P, Lepage N: A novel method for quantitation of acylglycines in human dried blood spots by UPLC-tandem mass spectrometry. Clin Biochem. 2018 Apr;54:131-138. doi: 10.1016/j.clinbiochem.2018.01.020. Epub 2018 Feb 2. [PubMed:29402417 ]
  6. (). Fenton, W.A., Gravel, R.A., Rosenblatt, D.S. Disorders of propionate and methylmalonate metabolism.. .
  7. (). Mayo Medical Laboratories 2005 Test Catalog. .