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Showing NP-Card for Isobutyrylglycine (NP0000743)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:17:57 UTC
NP-MRD IDNP0000743
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsobutyrylglycine
DescriptionIsobutyrylglycine 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. Isobutyrylglycine is identified in large amount in urine of patients with isobutyryl-CoA dehydrogenase deficiency. Isobutyryl-CoA dehydrogenase deficiency is a disorder caused by the deficiency of isobutyryl-CoA dehydrogenase that is involved in the catabolism of the branched-chain amino acid valine (PMID 15505379 ). Moreover, Isobutyrylglycine is found to be associated with ethylmalonic encephalopathy and propionic acidemia, which are also inborn errors of metabolism. Isobutyrylglycine is a biomarker for the consumption of cheese.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000743 (Isobutyrylglycine)

Isobutyrylglycine.mol
  Mrv1652305271900172D          

 10  9  0  0  0  0            999 V2000
   -1.4289   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0312    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
  8 10  1  0  0  0  0
  2  6  1  0  0  0  0
M  END
Download

3D MOL for NP0000743 (Isobutyrylglycine)

HMDB0000730
     RDKit          3D
Isobutyrylglycine
 21 20  0  0  0  0  0  0  0  0999 V2000
   -2.5996    0.9205   -0.9317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5855   -0.1342   -0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1025   -0.9407    0.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3069    0.5115   -0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1863    1.7727   -0.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8442   -0.2165    0.1091 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1147    0.3716    0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1218   -0.6573    0.7711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8507   -1.8886    0.8006 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971   -0.2113    1.0832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1134    1.7192   -1.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3303    0.4317   -1.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0744    1.2986   -0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4273   -0.8461   -1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5155   -1.9228    0.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9577   -0.3922    1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3241   -1.0870    1.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7621   -1.2543    0.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4496    0.9258   -0.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0862    1.0993    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8971    0.5001    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  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
  3 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 NP0000743 (Isobutyrylglycine)

Isobutyrylglycine.mol
  Mrv1652305271900172D          

 10  9  0  0  0  0            999 V2000
   -1.4289   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.0312    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
  8 10  1  0  0  0  0
  2  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000743

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO3/c1-4(2)6(10)7-3-5(8)9/h4H,3H2,1-2H3,(H,7,10)(H,8,9)

> <INCHI_KEY>
DCICDMMXFIELDF-UHFFFAOYSA-N

> <FORMULA>
C6H11NO3

> <MOLECULAR_WEIGHT>
145.1564

> <EXACT_MASS>
145.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
14.569462707724016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(2-methylpropanamido)acetic acid

> <ALOGPS_LOGP>
-0.11

> <JCHEM_LOGP>
-0.08510682866666647

> <ALOGPS_LOGS>
-0.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.762853347112124

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.0629876465018375

> <JCHEM_PKA_STRONGEST_BASIC>
-1.8019866084514846

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
34.6486

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isobutyrylglycine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000743 (Isobutyrylglycine)

HMDB0000730
     RDKit          3D
Isobutyrylglycine
 21 20  0  0  0  0  0  0  0  0999 V2000
   -2.5996    0.9205   -0.9317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5855   -0.1342   -0.5644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1025   -0.9407    0.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3069    0.5115   -0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1863    1.7727   -0.3414 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8442   -0.2165    0.1091 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1147    0.3716    0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1218   -0.6573    0.7711 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8507   -1.8886    0.8006 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3971   -0.2113    1.0832 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1134    1.7192   -1.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3303    0.4317   -1.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0744    1.2986   -0.0197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4273   -0.8461   -1.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5155   -1.9228    0.2995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9577   -0.3922    1.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3241   -1.0870    1.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7621   -1.2543    0.1740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4496    0.9258   -0.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0862    1.0993    1.2382 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8971    0.5001    0.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  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
  3 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 NP0000743 (Isobutyrylglycine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Isobutyrylglycine.mol                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      -2.667  -0.385   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.000  -0.385   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -1.334   0.385   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.667  -1.925   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -4.001   0.385   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   0.385   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334   1.925   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -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   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for NP0000743 (Isobutyrylglycine)

COMPND    HMDB0000730
HETATM    1  C1  UNL     1      -2.600   0.921  -0.932  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.586  -0.134  -0.564  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.103  -0.941   0.610  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.307   0.512  -0.268  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.186   1.773  -0.341  1.00  0.00           O  
HETATM    6  N1  UNL     1       0.844  -0.216   0.109  1.00  0.00           N  
HETATM    7  C5  UNL     1       2.115   0.372   0.408  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.122  -0.657   0.771  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.851  -1.889   0.801  1.00  0.00           O  
HETATM   10  O3  UNL     1       4.397  -0.211   1.083  1.00  0.00           O  
HETATM   11  H1  UNL     1      -2.113   1.719  -1.545  1.00  0.00           H  
HETATM   12  H2  UNL     1      -3.330   0.432  -1.628  1.00  0.00           H  
HETATM   13  H3  UNL     1      -3.074   1.299  -0.020  1.00  0.00           H  
HETATM   14  H4  UNL     1      -1.427  -0.846  -1.396  1.00  0.00           H  
HETATM   15  H5  UNL     1      -2.515  -1.923   0.300  1.00  0.00           H  
HETATM   16  H6  UNL     1      -2.958  -0.392   1.100  1.00  0.00           H  
HETATM   17  H7  UNL     1      -1.324  -1.087   1.381  1.00  0.00           H  
HETATM   18  H8  UNL     1       0.762  -1.254   0.174  1.00  0.00           H  
HETATM   19  H9  UNL     1       2.450   0.926  -0.513  1.00  0.00           H  
HETATM   20  H10 UNL     1       2.086   1.099   1.238  1.00  0.00           H  
HETATM   21  H11 UNL     1       4.897   0.500   0.610  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3    4   14
CONECT    3   15   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 NP0000743 (Isobutyrylglycine)

CC(C)C(=O)NCC(O)=O
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INCHI for NP0000743 (Isobutyrylglycine)

InChI=1S/C6H11NO3/c1-4(2)6(10)7-3-5(8)9/h4H,3H2,1-2H3,(H,7,10)(H,8,9)
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View in JSmol
Synonyms
ValueSource
IsobutanoylglycineChEBI
N-IsobutanoylglycineChEBI
N-(1-Methylpropyl)glycineHMDB
N-IsobutyrylglycineHMDB
IsobutyrylglycineChEBI
Chemical FormulaC6H11NO3
Average Mass145.1564 Da
Monoisotopic Mass145.07389 Da
IUPAC Name2-(2-methylpropanamido)acetic acid
Traditional Nameisobutyrylglycine
CAS Registry Number15926-18-8
SMILES
CC(C)C(=O)NCC(O)=O
InChI Identifier
InChI=1S/C6H11NO3/c1-4(2)6(10)7-3-5(8)9/h4H,3H2,1-2H3,(H,7,10)(H,8,9)
InChI KeyDCICDMMXFIELDF-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, 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
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
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
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point82.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility17.9 g/LALOGPS
logP-0.11ALOGPS
logP-0.085ChemAxon
logS-0.91ALOGPS
pKa (Strongest Acidic)4.06ChemAxon
pKa (Strongest Basic)-1.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity34.65 m³·mol⁻¹ChemAxon
Polarizability14.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000730
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022208
KNApSAcK IDC00052325
Chemspider ID9030891
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5698
PubChem Compound10855600
PDB IDNot Available
ChEBI ID70979
Good Scents IDNot Available
References
General References
  1. Goodman SI, McCabe ER, Fennessey PV, Mace JW: Multiple acyl-CoA dehydrogenase deficiency (glutaric aciduria type II) with transient hypersarcosinemia and sarcosinuria; possible inherited deficiency of an electron transfer flavoprotein. Pediatr Res. 1980 Jan;14(1):12-7. [PubMed:7360517 ]
  2. Liang Y, Liu L, Wei H, Luo XP, Wang MT: [Late-onset riboflavin-responsive multiple acyl-CoA dehydrogenase deficiency (glutaric aciduria type II)]. Zhonghua Er Ke Za Zhi. 2003 Dec;41(12):916-20. [PubMed:14723814 ]
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