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Showing NP-Card for 3-Methylcrotonylglycine (NP0000474)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-11-24 22:15:48 UTC
NP-MRD IDNP0000474
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Methylcrotonylglycine
Description3-Methylcrotonylglycine 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. 3-Methylcrotonylglycine is a normal amino acid metabolite found in urine. Increased levels of this metabolite are found in patients suffering from leucine catabolic disorders, such as 3-methylcrotonyl-CoA carboxylase deficiency. 3-Methylcrotonylglycine is often considered to be a diagnostic marker of organic acidemias (PMID 11170888 ). Moreover, 3-methylcrotonylglycine is found to be associated with 3-hydroxy-3-methylglutaryl-CoA lyase deficiency and propionic acidemia, which are also inborn errors of metabolism.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000474 (3-Methylcrotonylglycine)

3-Methylcrotonylglycine.mol
  Mrv1652305261923582D          

 11 10  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    1.0313    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   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.0313    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
   -1.7862   -0.2063    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
   -2.5006    0.2062    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  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  2  6  1  0  0  0  0
M  END
Download

3D MOL for NP0000474 (3-Methylcrotonylglycine)

HMDB0000459
     RDKit          3D
3-Methylcrotonylglycine
 22 21  0  0  0  0  0  0  0  0999 V2000
   -2.4393    1.3542   -0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462   -0.0941   -0.2671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4778   -0.9431   -0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0460   -0.6023   -0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1397    0.1853   -0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001    1.4256    0.0201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212   -0.4260   -0.1333 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6491    0.3116    0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7945   -0.6079   -0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5909   -1.8326   -0.1949 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1136   -0.1856    0.0685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214    1.6532    0.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5391    1.5638   -0.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9416    1.9568   -0.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0130   -0.5392   -1.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2271   -1.9995   -0.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1519   -0.7569    0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9619   -1.6789   -0.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4599   -1.4612   -0.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7109    1.1315   -0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6559    0.8043    1.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4296    0.7411   -0.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
 11 22  1  0
M  END
Download

3D SDF for NP0000474 (3-Methylcrotonylglycine)

3-Methylcrotonylglycine.mol
  Mrv1652305261923582D          

 11 10  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    1.0313    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   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.0313    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
   -1.7862   -0.2063    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
   -2.5006    0.2062    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  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  2  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000474

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H11NO3/c1-5(2)3-6(9)8-4-7(10)11/h3H,4H2,1-2H3,(H,8,9)(H,10,11)

> <INCHI_KEY>
PFWQSHXPNKRLIV-UHFFFAOYSA-N

> <FORMULA>
C7H11NO3

> <MOLECULAR_WEIGHT>
157.1671

> <EXACT_MASS>
157.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
15.786354849510554

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3-methylbut-2-enamido)acetic acid

> <ALOGPS_LOGP>
0.02

> <JCHEM_LOGP>
0.05766031933333371

> <ALOGPS_LOGS>
-1.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.847161126120916

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.091235532662606

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5390016178424107

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
40.050399999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.64e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3-methylbut-2-enamido)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000474 (3-Methylcrotonylglycine)

HMDB0000459
     RDKit          3D
3-Methylcrotonylglycine
 22 21  0  0  0  0  0  0  0  0999 V2000
   -2.4393    1.3542   -0.1075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2462   -0.0941   -0.2671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4778   -0.9431   -0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0460   -0.6023   -0.2699 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1397    0.1853   -0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1001    1.4256    0.0201 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4212   -0.4260   -0.1333 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6491    0.3116    0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7945   -0.6079   -0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5909   -1.8326   -0.1949 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1136   -0.1856    0.0685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214    1.6532    0.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5391    1.5638   -0.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9416    1.9568   -0.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0130   -0.5392   -1.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2271   -1.9995   -0.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1519   -0.7569    0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9619   -1.6789   -0.3913 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4599   -1.4612   -0.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7109    1.1315   -0.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6559    0.8043    1.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4296    0.7411   -0.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  7 19  1  0
  8 20  1  0
  8 21  1  0
 11 22  1  0
M  END
Download

PDB for NP0000474 (3-Methylcrotonylglycine)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 3-Methylcrotonylglycine.mol                       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-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      -3.334  -1.925   0.000  0.00  0.00           C+0
HETATM   11  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   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
Download

3D PDB for NP0000474 (3-Methylcrotonylglycine)

COMPND    HMDB0000459
HETATM    1  C1  UNL     1      -2.439   1.354  -0.107  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.246  -0.094  -0.267  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.478  -0.943  -0.424  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.046  -0.602  -0.270  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.140   0.185  -0.122  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.100   1.426   0.020  1.00  0.00           O  
HETATM    7  N1  UNL     1       1.421  -0.426  -0.133  1.00  0.00           N  
HETATM    8  C6  UNL     1       2.649   0.312   0.010  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.794  -0.608  -0.043  1.00  0.00           C  
HETATM   10  O2  UNL     1       3.591  -1.833  -0.195  1.00  0.00           O  
HETATM   11  O3  UNL     1       5.114  -0.186   0.069  1.00  0.00           O  
HETATM   12  H1  UNL     1      -2.021   1.653   0.896  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.539   1.564  -0.099  1.00  0.00           H  
HETATM   14  H3  UNL     1      -1.942   1.957  -0.912  1.00  0.00           H  
HETATM   15  H4  UNL     1      -4.013  -0.539  -1.308  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.227  -2.000  -0.569  1.00  0.00           H  
HETATM   17  H6  UNL     1      -4.152  -0.757   0.445  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.962  -1.679  -0.391  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.460  -1.461  -0.252  1.00  0.00           H  
HETATM   20  H9  UNL     1       2.711   1.132  -0.752  1.00  0.00           H  
HETATM   21  H10 UNL     1       2.656   0.804   1.024  1.00  0.00           H  
HETATM   22  H11 UNL     1       5.430   0.741  -0.186  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4    4
CONECT    3   15   16   17
CONECT    4    5   18
CONECT    5    6    6    7
CONECT    7    8   19
CONECT    8    9   20   21
CONECT    9   10   10   11
CONECT   11   22
END
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SMILES for NP0000474 (3-Methylcrotonylglycine)

CC(C)=CC(=O)NCC(O)=O
Download

INCHI for NP0000474 (3-Methylcrotonylglycine)

InChI=1S/C7H11NO3/c1-5(2)3-6(9)8-4-7(10)11/h3H,4H2,1-2H3,(H,8,9)(H,10,11)
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View in JSmol
Synonyms
ValueSource
beta-MethylcrotonylglycineChEBI
b-MethylcrotonylglycineGenerator
Β-methylcrotonylglycineGenerator
3-Methylcrotonyl glycineHMDB
3-Methylcrotonyl-glycineHMDB
3-MethylcrotonylglycinHMDB
N-(3-Methyl-1-oxo-2-butenyl)-glycineHMDB
3-MethylcrotonylglycineMeSH
Chemical FormulaC7H11NO3
Average Mass157.1671 Da
Monoisotopic Mass157.07389 Da
IUPAC Name2-(3-methylbut-2-enamido)acetic acid
Traditional Name(3-methylbut-2-enamido)acetic acid
CAS Registry Number33008-07-0
SMILES
CC(C)=CC(=O)NCC(O)=O
InChI Identifier
InChI=1S/C7H11NO3/c1-5(2)3-6(9)8-4-7(10)11/h3H,4H2,1-2H3,(H,8,9)(H,10,11)
InChI KeyPFWQSHXPNKRLIV-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
Apis ceranaLOTUS Database
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
  • N-acyl-amine
  • 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.64 g/LALOGPS
logP0.02ALOGPS
logP0.058ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)4.09ChemAxon
pKa (Strongest Basic)-0.54ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity40.05 m³·mol⁻¹ChemAxon
Polarizability15.79 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000459
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022057
KNApSAcK IDNot Available
Chemspider ID148224
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5447
PubChem Compound169485
PDB IDNot Available
ChEBI ID68499
Good Scents IDNot Available
References
General References
  1. Gallardo ME, Desviat LR, Rodriguez JM, Esparza-Gordillo J, Perez-Cerda C, Perez B, Rodriguez-Pombo P, Criado O, Sanz R, Morton DH, Gibson KM, Le TP, Ribes A, de Cordoba SR, Ugarte M, Penalva MA: The molecular basis of 3-methylcrotonylglycinuria, a disorder of leucine catabolism. Am J Hum Genet. 2001 Feb;68(2):334-46. Epub 2001 Jan 17. [PubMed:11170888 ]
  2. Chantin C, Bonin B, Boulieu R, Bory C: Liquid-chromatographic study of purine metabolism abnormalities in purine nucleoside phosphorylase deficiency. Clin Chem. 1996 Feb;42(2):326-8. [PubMed:8595732 ]
  3. Wysocki SJ, Hahnel R: 3-Methylcrotonylglycine excretion in 3-hydroxy-3-methylglutaric aciduria. Clin Chim Acta. 1978 May 16;86(1):101-8. [PubMed:657530 ]
  4. Koeberl DD, Millington DS, Smith WE, Weavil SD, Muenzer J, McCandless SE, Kishnani PS, McDonald MT, Chaing S, Boney A, Moore E, Frazier DM: Evaluation of 3-methylcrotonyl-CoA carboxylase deficiency detected by tandem mass spectrometry newborn screening. J Inherit Metab Dis. 2003;26(1):25-35. [PubMed:12872837 ]
  5. Baykal T, Gokcay GH, Ince Z, Dantas MF, Fowler B, Baumgartner MR, Demir F, Can G, Demirkol M: Consanguineous 3-methylcrotonyl-CoA carboxylase deficiency: early-onset necrotizing encephalopathy with lethal outcome. J Inherit Metab Dis. 2005;28(2):229-33. [PubMed:15877210 ]
  6. Cowan MJ, Wara DW, Packman S, Ammann AJ, Yoshino M, Sweetman L, Nyhan W: Multiple biotin-dependent carboxylase deficiencies associated with defects in T-cell and B-cell immunity. Lancet. 1979 Jul 21;2(8134):115-8. [PubMed:88554 ]