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Showing NP-Card for N-Butyrylglycine (NP0000502)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:16:00 UTC
NP-MRD IDNP0000502
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Butyrylglycine
DescriptionN-Butyrylglycine 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, such as ethylmalonic encephalopathy. 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 amino acids composed of glycine substituted at the nitrogen rather than the usual carbon position, resulting in the loss of hydrogen bonding donors. Polymers of these compounds are called Peptoids.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000502 (N-Butyrylglycine)

N-Butyrylglycine.mol
  Mrv1652305271900222D          

 10  9  0  0  0  0            999 V2000
    1.7862   -0.2063    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
    1.0717    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.2062    0.0000 O   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
   -0.3572    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2063    0.0000 C   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
   -2.5006   -0.2063    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
  9 10  1  0  0  0  0
  2  6  1  0  0  0  0
M  END
Download

3D MOL for NP0000502 (N-Butyrylglycine)

HMDB0000808
     RDKit          3D
N-Butyrylglycine
 21 20  0  0  0  0  0  0  0  0999 V2000
   -3.7816    0.1242   -0.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696    0.5443   -0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3621   -0.3002    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    0.2392   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0889    1.2399   -0.8058 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1767   -0.3280    0.4621 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4507    0.2578    0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799   -0.4766    0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3620   -1.4774    1.4963 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8910   -0.0745    0.5496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2940   -0.0446   -1.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431    0.9465    0.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8014   -0.7839    0.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1075    0.5186   -1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126    1.6007   -0.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5228   -0.3820    1.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3514   -1.3536   -0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1650   -1.1660    1.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4773    1.3391    0.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5293    0.1914   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4258   -0.6146   -0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
 10 21  1  0
M  END
Download

3D SDF for NP0000502 (N-Butyrylglycine)

N-Butyrylglycine.mol
  Mrv1652305271900222D          

 10  9  0  0  0  0            999 V2000
    1.7862   -0.2063    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
    1.0717    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.2062    0.0000 O   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
   -0.3572    1.0312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2063    0.0000 C   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
   -2.5006   -0.2063    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
  9 10  1  0  0  0  0
  2  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000502

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO3/c1-2-3-5(8)7-4-6(9)10/h2-4H2,1H3,(H,7,8)(H,9,10)

> <INCHI_KEY>
WPSSBBPLVMTKRN-UHFFFAOYSA-N

> <FORMULA>
C6H11NO3

> <MOLECULAR_WEIGHT>
145.1564

> <EXACT_MASS>
145.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
14.63825075516502

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-butanamidoacetic acid

> <ALOGPS_LOGP>
0.03

> <JCHEM_LOGP>
-0.18352444200000004

> <ALOGPS_LOGS>
-0.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.809584079020865

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.062989857092291

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8713891837814174

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
34.6751

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.76e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butyrylglycine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000502 (N-Butyrylglycine)

HMDB0000808
     RDKit          3D
N-Butyrylglycine
 21 20  0  0  0  0  0  0  0  0999 V2000
   -3.7816    0.1242   -0.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3696    0.5443   -0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3621   -0.3002    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0003    0.2392   -0.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0889    1.2399   -0.8058 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1767   -0.3280    0.4621 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4507    0.2578    0.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5799   -0.4766    0.7554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3620   -1.4774    1.4963 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8910   -0.0745    0.5496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2940   -0.0446   -1.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3431    0.9465    0.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8014   -0.7839    0.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1075    0.5186   -1.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2126    1.6007   -0.1107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5228   -0.3820    1.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3514   -1.3536   -0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1650   -1.1660    1.0952 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4773    1.3391    0.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5293    0.1914   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4258   -0.6146   -0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
 10 21  1  0
M  END
Download

PDB for NP0000502 (N-Butyrylglycine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: N-Butyrylglycine.mol                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       3.334  -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       2.001   0.385   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.334  -1.925   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.668   0.385   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.667   0.385   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.667   1.925   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.001  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.334   0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.668  -0.385   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    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for NP0000502 (N-Butyrylglycine)

COMPND    HMDB0000808
HETATM    1  C1  UNL     1      -3.782   0.124  -0.252  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.370   0.544  -0.464  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.362  -0.300   0.250  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.000   0.239  -0.056  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.089   1.240  -0.806  1.00  0.00           O  
HETATM    6  N1  UNL     1       1.177  -0.328   0.462  1.00  0.00           N  
HETATM    7  C5  UNL     1       2.451   0.258   0.115  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.580  -0.477   0.755  1.00  0.00           C  
HETATM    9  O2  UNL     1       3.362  -1.477   1.496  1.00  0.00           O  
HETATM   10  O3  UNL     1       4.891  -0.075   0.550  1.00  0.00           O  
HETATM   11  H1  UNL     1      -4.294  -0.045  -1.237  1.00  0.00           H  
HETATM   12  H2  UNL     1      -4.343   0.946   0.237  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.801  -0.784   0.377  1.00  0.00           H  
HETATM   14  H4  UNL     1      -2.108   0.519  -1.551  1.00  0.00           H  
HETATM   15  H5  UNL     1      -2.213   1.601  -0.111  1.00  0.00           H  
HETATM   16  H6  UNL     1      -1.523  -0.382   1.331  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.351  -1.354  -0.144  1.00  0.00           H  
HETATM   18  H8  UNL     1       1.165  -1.166   1.095  1.00  0.00           H  
HETATM   19  H9  UNL     1       2.477   1.339   0.398  1.00  0.00           H  
HETATM   20  H10 UNL     1       2.529   0.191  -1.007  1.00  0.00           H  
HETATM   21  H11 UNL     1       5.426  -0.615  -0.139  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4   16   17
CONECT    4    5    5    6
CONECT    6    7   18
CONECT    7    8   19   20
CONECT    8    9    9   10
CONECT   10   21
END
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SMILES for NP0000502 (N-Butyrylglycine)

CCCC(=O)NCC(O)=O
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INCHI for NP0000502 (N-Butyrylglycine)

InChI=1S/C6H11NO3/c1-2-3-5(8)7-4-6(9)10/h2-4H2,1H3,(H,7,8)(H,9,10)
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View in JSmol
Synonyms
ValueSource
2-Butanamidoacetic acidChEBI
2-Butyramidoacetic acidChEBI
Butanamidoacetic acidChEBI
Butyramidoacetic acidChEBI
N-(1-Oxobutyl)glycineChEBI
N-Butyryl-glycineChEBI
2-ButanamidoacetateGenerator
2-ButyramidoacetateGenerator
ButanamidoacetateGenerator
ButyramidoacetateGenerator
N-ButanoylglycineHMDB
ButyrylglycineHMDB
N-ButyrylglycineChEBI
Chemical FormulaC6H11NO3
Average Mass145.1564 Da
Monoisotopic Mass145.07389 Da
IUPAC Name2-butanamidoacetic acid
Traditional Namebutyrylglycine
CAS Registry Number20208-73-5
SMILES
CCCC(=O)NCC(O)=O
InChI Identifier
InChI=1S/C6H11NO3/c1-2-3-5(8)7-4-6(9)10/h2-4H2,1H3,(H,7,8)(H,9,10)
InChI KeyWPSSBBPLVMTKRN-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
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 Solubility17.6 g/LALOGPS
logP0.03ALOGPS
logP-0.18ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)4.06ChemAxon
pKa (Strongest Basic)-1.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.68 m³·mol⁻¹ChemAxon
Polarizability14.64 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000808
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022256
KNApSAcK IDNot Available
Chemspider ID79766
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5772
PubChem Compound88412
PDB IDNot Available
ChEBI ID89963
Good Scents IDNot Available
References
General References
  1. Tein I, Haslam RH, Rhead WJ, Bennett MJ, Becker LE, Vockley J: Short-chain acyl-CoA dehydrogenase deficiency: a cause of ophthalmoplegia and multicore myopathy. Neurology. 1999 Jan 15;52(2):366-72. [PubMed:9932958 ]
  2. Bhala A, Willi SM, Rinaldo P, Bennett MJ, Schmidt-Sommerfeld E, Hale DE: Clinical and biochemical characterization of short-chain acyl-coenzyme A dehydrogenase deficiency. J Pediatr. 1995 Jun;126(6):910-5. [PubMed:7776094 ]
  3. 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 ]
  4. Dawson DB, Waber L, Hale DE, Bennett MJ: Transient organic aciduria and persistent lacticacidemia in a patient with short-chain acyl-coenzyme A dehydrogenase deficiency. J Pediatr. 1995 Jan;126(1):69-71. [PubMed:7815229 ]
  5. Hagen T, Korson MS, Sakamoto M, Evans JE: A GC/MS/MS screening method for multiple organic acidemias from urine specimens. Clin Chim Acta. 1999 May;283(1-2):77-88. [PubMed:10404733 ]