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Showing NP-Card for Hexanoylglycine (NP0000564)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:16:29 UTC
NP-MRD IDNP0000564
Secondary Accession NumbersNone
Natural Product Identification
Common NameHexanoylglycine
DescriptionHexanoylglycine 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-acylglycineHexanoylglycine is a fatty acid metabolite, it appears in the urine of patients with hereditary medium-chain acyl-CoA dehydrogenase (MCAD) deficiency (PMID 2775902 ), which is a genetic disorder.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000564 (Hexanoylglycine)

Hexanoylglycine.mol
  Mrv1652305271900152D          

 12 11  0  0  0  0            999 V2000
    2.2688    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312   -0.3572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4438    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6813    1.0717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6813   -0.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2063   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0312   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4438   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2687   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6813    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063    0.3572    0.0000 O   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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 12  2  0  0  0  0
  2  6  1  0  0  0  0
M  END
Download

3D MOL for NP0000564 (Hexanoylglycine)

HMDB0000701
     RDKit          3D
Hexanoylglycine
 27 26  0  0  0  0  0  0  0  0999 V2000
   -4.4897   -0.4431   -0.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0530    0.1031   -0.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5305    0.0080    0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177    0.5091    1.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1679   -0.2767    0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2347    0.1931    0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4684    1.1390    1.1452 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2993   -0.4013   -0.3464 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6347    0.0984   -0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6361   -0.6215   -0.9602 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3097   -1.5647   -1.7229 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -0.2724   -0.8978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4017   -1.5268   -0.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0680   -0.0867   -1.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9170   -0.0715    0.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4513   -0.5614   -1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0464    1.1338   -0.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6394   -1.0470    1.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2297    0.5881    1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0796    1.5871    0.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8870    0.4136    2.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   -1.3539    0.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5117   -0.1381   -0.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1785   -1.1949   -1.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8782   -0.0467    0.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6697    1.1897   -0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5129   -0.6470   -0.1090 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  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 12 27  1  0
M  END
Download

3D SDF for NP0000564 (Hexanoylglycine)

Hexanoylglycine.mol
  Mrv1652305271900152D          

 12 11  0  0  0  0            999 V2000
    2.2688    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312   -0.3572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4438    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6813    1.0717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6813   -0.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2063   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0312   -1.0717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4438   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2687   -0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6813    0.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2063    0.3572    0.0000 O   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  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 12  2  0  0  0  0
  2  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000564

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C8H15NO3/c1-2-3-4-5-7(10)9-6-8(11)12/h2-6H2,1H3,(H,9,10)(H,11,12)

> <INCHI_KEY>
UPCKIPHSXMXJOX-UHFFFAOYSA-N

> <FORMULA>
C8H15NO3

> <MOLECULAR_WEIGHT>
173.2096

> <EXACT_MASS>
173.105193351

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.745990944221177

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hexanamidoacetic acid

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
0.7056128879999999

> <ALOGPS_LOGS>
-1.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.99295114693626

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.251619753846688

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6781919217097747

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
43.8771

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexanoylglycine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000564 (Hexanoylglycine)

HMDB0000701
     RDKit          3D
Hexanoylglycine
 27 26  0  0  0  0  0  0  0  0999 V2000
   -4.4897   -0.4431   -0.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0530    0.1031   -0.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5305    0.0080    0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177    0.5091    1.0632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1679   -0.2767    0.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2347    0.1931    0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4684    1.1390    1.1452 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2993   -0.4013   -0.3464 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6347    0.0984   -0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6361   -0.6215   -0.9602 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3097   -1.5647   -1.7229 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9750   -0.2724   -0.8978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4017   -1.5268   -0.3800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0680   -0.0867   -1.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9170   -0.0715    0.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4513   -0.5614   -1.1782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0464    1.1338   -0.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6394   -1.0470    1.2195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2297    0.5881    1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0796    1.5871    0.8028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8870    0.4136    2.1515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2068   -1.3539    0.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5117   -0.1381   -0.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1785   -1.1949   -1.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8782   -0.0467    0.9348 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6697    1.1897   -0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5129   -0.6470   -0.1090 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  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 12 27  1  0
M  END
Download

PDB for NP0000564 (Hexanoylglycine)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Hexanoylglycine.mol                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       4.235   0.667   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.925  -0.667   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.695   0.667   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.005   2.001   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.005  -0.667   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.385  -0.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.385  -2.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.925  -2.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.695  -0.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.235  -0.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.005   0.667   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.385   0.667   0.000  0.00  0.00           O+0
CONECT    1    3    4    5                                                  
CONECT    2    3    6                                                       
CONECT    3    2    1                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    7   12    2                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    6                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for NP0000564 (Hexanoylglycine)

COMPND    HMDB0000701
HETATM    1  C1  UNL     1      -4.490  -0.443  -0.454  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.053   0.103  -0.505  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.530   0.008   0.894  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.118   0.509   1.063  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.168  -0.277   0.208  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.235   0.193   0.364  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.468   1.139   1.145  1.00  0.00           O  
HETATM    8  N1  UNL     1       2.299  -0.401  -0.346  1.00  0.00           N  
HETATM    9  C7  UNL     1       3.635   0.098  -0.152  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.636  -0.622  -0.960  1.00  0.00           C  
HETATM   11  O2  UNL     1       4.310  -1.565  -1.723  1.00  0.00           O  
HETATM   12  O3  UNL     1       5.975  -0.272  -0.898  1.00  0.00           O  
HETATM   13  H1  UNL     1      -4.402  -1.527  -0.380  1.00  0.00           H  
HETATM   14  H2  UNL     1      -5.068  -0.087  -1.329  1.00  0.00           H  
HETATM   15  H3  UNL     1      -4.917  -0.072   0.502  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.451  -0.561  -1.178  1.00  0.00           H  
HETATM   17  H5  UNL     1      -3.046   1.134  -0.911  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.639  -1.047   1.219  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.230   0.588   1.549  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.080   1.587   0.803  1.00  0.00           H  
HETATM   21  H9  UNL     1      -0.887   0.414   2.152  1.00  0.00           H  
HETATM   22  H10 UNL     1      -0.207  -1.354   0.406  1.00  0.00           H  
HETATM   23  H11 UNL     1      -0.512  -0.138  -0.859  1.00  0.00           H  
HETATM   24  H12 UNL     1       2.178  -1.195  -1.016  1.00  0.00           H  
HETATM   25  H13 UNL     1       3.878  -0.047   0.935  1.00  0.00           H  
HETATM   26  H14 UNL     1       3.670   1.190  -0.419  1.00  0.00           H  
HETATM   27  H15 UNL     1       6.513  -0.647  -0.109  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16   17
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6   22   23
CONECT    6    7    7    8
CONECT    8    9   24
CONECT    9   10   25   26
CONECT   10   11   11   12
CONECT   12   27
END
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SMILES for NP0000564 (Hexanoylglycine)

CCCCCC(=O)NCC(O)=O
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INCHI for NP0000564 (Hexanoylglycine)

InChI=1S/C8H15NO3/c1-2-3-4-5-7(10)9-6-8(11)12/h2-6H2,1H3,(H,9,10)(H,11,12)
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View in JSmol
Synonyms
ValueSource
CaproylglycineChEBI
N-(1-Oxohexyl)glycineChEBI
N-CaproylglycineChEBI
N-Hexanoyl-glycineHMDB
N-HexanoylglycineHMDB
HexanoylglycineChEBI
Chemical FormulaC8H15NO3
Average Mass173.2096 Da
Monoisotopic Mass173.10519 Da
IUPAC Name2-hexanamidoacetic acid
Traditional Namehexanoylglycine
CAS Registry Number24003-67-6
SMILES
CCCCCC(=O)NCC(O)=O
InChI Identifier
InChI=1S/C8H15NO3/c1-2-3-4-5-7(10)9-6-8(11)12/h2-6H2,1H3,(H,9,10)(H,11,12)
InChI KeyUPCKIPHSXMXJOX-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, CDCl3, 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
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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 Descriptors
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 Solubility3.61 g/LALOGPS
logP0.9ALOGPS
logP0.71ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)4.25ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity43.88 m³·mol⁻¹ChemAxon
Polarizability18.75 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000701
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022190
KNApSAcK IDNot Available
Chemspider ID89859
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5669
PubChem Compound99463
PDB IDNot Available
ChEBI ID64390
Good Scents IDNot Available
References
General References
  1. Rinaldo P, O'Shea JJ, Welch RD, Tanaka K: Stable isotope dilution analysis of n-hexanoylglycine, 3-phenylpropionylglycine and suberylglycine in human urine using chemical ionization gas chromatography/mass spectrometry selected ion monitoring. Biomed Environ Mass Spectrom. 1989 Jul;18(7):471-7. [PubMed:2775902 ]
  2. Chabrol B, Mancini J, Bertrand C, Vianey-Saban C, Divry P, Livet MO, Pinsard N: [Generalized epilepsy disclosing medium-chain-acyl-CoA dehydrogenase deficiency]. Arch Fr Pediatr. 1993 Jun-Jul;50(6):497-500. [PubMed:8135611 ]
  3. Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71. [PubMed:2380628 ]
  4. Yamaguchi S, Shimizu N, Orii T, Fukao T, Suzuki Y, Maeda K, Hashimoto T, Previs SF, Rinaldo P: Prenatal diagnosis and neonatal monitoring of a fetus with glutaric aciduria type II due to electron transfer flavoprotein (beta-subunit) deficiency. Pediatr Res. 1991 Nov;30(5):439-43. [PubMed:1754299 ]