NP-MRD: Showing NP-Card for Isovalerylglutamic acid (NP0001057)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:20:28 UTC

NP-MRD ID

NP0001057

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isovalerylglutamic acid

Description

Isovalerylglutamic acid is an unusual mtabolite that has been found in the urine of patients with Isovaleric Acidemia due to Isovaleryl-CoA Dehydrogenase Deficiency (OMMBID: The Metabolic and Molecular Bases of Inherited Disease, Ch.93: Branched Chain Organic Acidurias). And in Multiple acyl-Co A dehydrogenation deficiency (MADD) (PMID 6862997 ). Isovalerylglutamate is a biomarker for the consumption of cheese.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000726
     RDKit          3D
Isovalerylglutamic acid
 33 32  0  0  0  0  0  0  0  0999 V2000
   -2.8371    1.3509    2.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4037    1.2872    0.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2030    2.5832    0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180    0.1463    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2491    0.3806   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7935    1.4249    0.4863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3641   -0.5341   -0.6243 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0779   -0.2659   -0.6544 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7265   -1.4113    0.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2107   -1.2422    0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8290   -2.3872    0.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562   -3.2611    1.3305 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1931   -2.4655    1.0571 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5440   -0.2108   -2.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7357   -0.4438   -3.0047 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8341    0.0860   -2.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6766    1.1336    2.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0385    0.6019    2.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4577    2.3566    2.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4939    1.0313    0.7590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1776    3.0765   -0.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5219    3.2834    0.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7581    2.4018   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1593    0.1174   -0.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8837   -0.7972    0.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6833   -1.4190   -1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2368    0.6995   -0.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4856   -2.3417   -0.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2781   -1.4623    1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6595   -1.3414   -0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5311   -0.2623    0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7315   -1.8381    1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891   -0.2773   -3.2456 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  7 26  1  0
  8 27  1  1
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 13 32  1  0
 16 33  1  0
M  END


  Mrv1652305271900172D          

 16 15  0  0  1  0            999 V2000
   11.3107   -9.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0732   -8.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5482   -7.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3732   -7.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3107   -8.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8982   -8.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1357   -6.5845    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.8982   -7.2990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7857   -8.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5482   -5.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3107   -6.5845    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0732   -7.2990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6108   -8.0134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3732   -8.7280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1357   -5.1556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3732   -5.8700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  6  1  0  0  0  0
  7  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
  7 11  1  6  0  0  0
  7 10  1  0  0  0  0
  8 12  2  0  0  0  0
  8 11  1  0  0  0  0
  9 13  1  0  0  0  0
  9 14  2  0  0  0  0
 10 15  1  0  0  0  0
 10 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0001057

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)N[C@@H](CCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H17NO5/c1-6(2)5-8(12)11-7(10(15)16)3-4-9(13)14/h6-7H,3-5H2,1-2H3,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1

> <INCHI_KEY>
HCVIJONZMYVLAW-ZETCQYMHSA-N

> <FORMULA>
C10H17NO5

> <MOLECULAR_WEIGHT>
231.2457

> <EXACT_MASS>
231.110672659

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.33075369813675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-(3-methylbutanamido)pentanedioic acid

> <ALOGPS_LOGP>
0.27

> <JCHEM_LOGP>
0.3191081916666665

> <ALOGPS_LOGS>
-1.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.557318681156051

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.723007734504288

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3837963217706424

> <JCHEM_POLAR_SURFACE_AREA>
103.70000000000002

> <JCHEM_REFRACTIVITY>
54.50800000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.32e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isovalerylglutamic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000726
     RDKit          3D
Isovalerylglutamic acid
 33 32  0  0  0  0  0  0  0  0999 V2000
   -2.8371    1.3509    2.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4037    1.2872    0.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2030    2.5832    0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180    0.1463    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2491    0.3806   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7935    1.4249    0.4863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3641   -0.5341   -0.6243 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0779   -0.2659   -0.6544 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7265   -1.4113    0.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2107   -1.2422    0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8290   -2.3872    0.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562   -3.2611    1.3305 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1931   -2.4655    1.0571 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5440   -0.2108   -2.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7357   -0.4438   -3.0047 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8341    0.0860   -2.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6766    1.1336    2.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0385    0.6019    2.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4577    2.3566    2.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4939    1.0313    0.7590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1776    3.0765   -0.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5219    3.2834    0.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7581    2.4018   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1593    0.1174   -0.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8837   -0.7972    0.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6833   -1.4190   -1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2368    0.6995   -0.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4856   -2.3417   -0.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2781   -1.4623    1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6595   -1.3414   -0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5311   -0.2623    0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7315   -1.8381    1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891   -0.2773   -3.2456 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  7 26  1  0
  8 27  1  1
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 13 32  1  0
 16 33  1  0
M  END

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      21.113 -17.626   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.803 -16.292   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.423 -13.625   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.963 -13.625   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.113 -14.958   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.343 -16.292   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.653 -12.291   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.343 -13.625   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.733 -14.958   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.423 -10.957   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      21.113 -12.291   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      18.803 -13.625   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      27.273 -14.958   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      24.963 -16.292   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      22.653  -9.624   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      24.963 -10.957   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    6                                                            
CONECT    3    7    4                                                       
CONECT    4    3    9                                                       
CONECT    5    6    8                                                       
CONECT    6    1    2    5                                                  
CONECT    7    3   11   10                                                  
CONECT    8    5   12   11                                                  
CONECT    9    4   13   14                                                  
CONECT   10    7   15   16                                                  
CONECT   11    7    8                                                       
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14    9                                                            
CONECT   15   10                                                            
CONECT   16   10                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0000726
HETATM    1  C1  UNL     1      -2.837   1.351   2.149  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.404   1.287   0.744  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.203   2.583   0.017  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.718   0.146   0.029  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.249   0.381  -0.023  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.793   1.425   0.486  1.00  0.00           O  
HETATM    7  N1  UNL     1      -0.364  -0.534  -0.624  1.00  0.00           N  
HETATM    8  C6  UNL     1       1.078  -0.266  -0.654  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.727  -1.411   0.070  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.211  -1.242   0.113  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.829  -2.387   0.874  1.00  0.00           C  
HETATM   12  O2  UNL     1       3.056  -3.261   1.330  1.00  0.00           O  
HETATM   13  O3  UNL     1       5.193  -2.466   1.057  1.00  0.00           O  
HETATM   14  C10 UNL     1       1.544  -0.211  -2.039  1.00  0.00           C  
HETATM   15  O4  UNL     1       0.736  -0.444  -3.005  1.00  0.00           O  
HETATM   16  O5  UNL     1       2.834   0.086  -2.413  1.00  0.00           O  
HETATM   17  H1  UNL     1      -3.677   1.134   2.856  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.039   0.602   2.300  1.00  0.00           H  
HETATM   19  H3  UNL     1      -2.458   2.357   2.380  1.00  0.00           H  
HETATM   20  H4  UNL     1      -4.494   1.031   0.759  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.178   3.076  -0.127  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.522   3.283   0.566  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.758   2.402  -1.002  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.159   0.117  -0.997  1.00  0.00           H  
HETATM   25  H9  UNL     1      -2.884  -0.797   0.565  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.683  -1.419  -1.063  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.237   0.700  -0.158  1.00  0.00           H  
HETATM   28  H12 UNL     1       1.486  -2.342  -0.494  1.00  0.00           H  
HETATM   29  H13 UNL     1       1.278  -1.462   1.098  1.00  0.00           H  
HETATM   30  H14 UNL     1       3.660  -1.341  -0.903  1.00  0.00           H  
HETATM   31  H15 UNL     1       3.531  -0.262   0.502  1.00  0.00           H  
HETATM   32  H16 UNL     1       5.732  -1.838   1.626  1.00  0.00           H  
HETATM   33  H17 UNL     1       3.289  -0.277  -3.246  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4   20
CONECT    3   21   22   23
CONECT    4    5   24   25
CONECT    5    6    6    7
CONECT    7    8   26
CONECT    8    9   14   27
CONECT    9   10   28   29
CONECT   10   11   30   31
CONECT   11   12   12   13
CONECT   13   32
CONECT   14   15   15   16
CONECT   16   33
END

HMDB0000726
     RDKit          3D
Isovalerylglutamic acid
 33 32  0  0  0  0  0  0  0  0999 V2000
   -2.8371    1.3509    2.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4037    1.2872    0.7443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2030    2.5832    0.0168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7180    0.1463    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2491    0.3806   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7935    1.4249    0.4863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3641   -0.5341   -0.6243 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0779   -0.2659   -0.6544 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7265   -1.4113    0.0697 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2107   -1.2422    0.1132 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8290   -2.3872    0.8738 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0562   -3.2611    1.3305 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1931   -2.4655    1.0571 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5440   -0.2108   -2.0394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7357   -0.4438   -3.0047 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8341    0.0860   -2.4133 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6766    1.1336    2.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0385    0.6019    2.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4577    2.3566    2.3799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4939    1.0313    0.7590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1776    3.0765   -0.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5219    3.2834    0.5657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7581    2.4018   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1593    0.1174   -0.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8837   -0.7972    0.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6833   -1.4190   -1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2368    0.6995   -0.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4856   -2.3417   -0.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2781   -1.4623    1.0984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6595   -1.3414   -0.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5311   -0.2623    0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7315   -1.8381    1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891   -0.2773   -3.2456 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  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
  8 14  1  0
 14 15  2  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  7 26  1  0
  8 27  1  1
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 13 32  1  0
 16 33  1  0
M  END

View in JSmol

Synonyms

Value	Source
Isovalerylglutamate	Generator
N-Isovaleryl-DL-glutamate	HMDB
N-Isovaleryl-DL-glutamic acid	HMDB
N-Isovalerylglutamic acid	HMDB
N-IVGA	HMDB
(2S)-2-[(1-Hydroxy-3-methylbutylidene)amino]pentanedioate	HMDB

Chemical Formula

C₁₀H₁₇NO₅

Average Mass

231.2457 Da

Monoisotopic Mass

231.11067 Da

IUPAC Name

(2S)-2-(3-methylbutanamido)pentanedioic acid

Traditional Name

isovalerylglutamic acid

CAS Registry Number

80154-63-8

SMILES

CC(C)CC(=O)N[C@@H](CCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C10H17NO5/c1-6(2)5-8(12)11-7(10(15)16)3-4-9(13)14/h6-7H,3-5H2,1-2H3,(H,11,12)(H,13,14)(H,15,16)/t7-/m0/s1

InChI Key

HCVIJONZMYVLAW-ZETCQYMHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamic acid and derivatives

Alternative Parents

Substituents

Glutamic acid or derivatives
N-acyl-l-alpha-amino acid
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Branched fatty acid
Dicarboxylic acid or derivatives
Fatty amide
Fatty acyl
Fatty acid
N-acyl-amine
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	6.32 g/L	ALOGPS
logP	0.27	ALOGPS
logP	0.32	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.72	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	103.7 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	54.51 m³·mol⁻¹	ChemAxon
Polarizability	23.33 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000726

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022204

KNApSAcK ID

Not Available

Chemspider ID

117667

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5694

PubChem Compound

133383

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Niederwieser A, Steinmann B, Exner U, Neuheiser F, Redweik U, Wang M, Rampini S, Wendel U: Multiple acyl-Co A dehydrogenation deficiency (MADD) in a boy with nonketotic hypoglycemia, hepatomegaly, muscle hypotonia and cardiomyopathy. Detection of N-isovalerylglutamic acid and its monoamide. Helv Paediatr Acta. 1983 Mar;38(1):9-26. [PubMed:6862997 ]
Feng Z, Sun X, Yang J, Hao D, Du L, Wang H, Xu W, Zhao X, Sun C: Metabonomics analysis of urine and plasma from rats given long-term and low-dose dimethoate by ultra-performance liquid chromatography-mass spectrometry. Chem Biol Interact. 2012 Sep 30;199(3):143-53. doi: 10.1016/j.cbi.2012.07.004. Epub 2012 Aug 3. [PubMed:22884955 ]

Showing NP-Card for Isovalerylglutamic acid (NP0001057)

MOL for NP0001057 (Isovalerylglutamic acid)

3D MOL for NP0001057 (Isovalerylglutamic acid)

3D SDF for NP0001057 (Isovalerylglutamic acid)

3D-SDF for NP0001057 (Isovalerylglutamic acid)

PDB for NP0001057 (Isovalerylglutamic acid)

3D PDB for NP0001057 (Isovalerylglutamic acid)

SMILES for NP0001057 (Isovalerylglutamic acid)

INCHI for NP0001057 (Isovalerylglutamic acid)

Structure for NP0001057 (Isovalerylglutamic acid)

3D Structure for NP0001057 (Isovalerylglutamic acid)