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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:47:52 UTC

HMDB ID

HMDB0000726

Secondary Accession Numbers

HMDB00726

Metabolite 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>
HMDB0000726

> <DATABASE_NAME>
hmdb

> <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 View NMR Assignments View Stereo Labels

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 Molecular Weight

231.2457

Monoisotopic Molecular Weight

231.110672659

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

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

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Solid

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	155.272	31661259
DarkChem	[M-H]-	150.974	31661259
AllCCS	[M+H]+	153.526	32859911
AllCCS	[M-H]-	152.222	32859911
DeepCCS	[M+H]+	158.847	30932474
DeepCCS	[M-H]-	156.489	30932474
DeepCCS	[M-2H]-	189.375	30932474
DeepCCS	[M+Na]+	165.515	30932474
AllCCS	[M+H]+	153.5	32859911
AllCCS	[M+H-H2O]+	150.2	32859911
AllCCS	[M+NH4]+	156.6	32859911
AllCCS	[M+Na]+	157.5	32859911
AllCCS	[M-H]-	152.2	32859911
AllCCS	[M+Na-2H]-	153.2	32859911
AllCCS	[M+HCOO]-	154.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isovalerylglutamic acid	CC(C)CC(=O)N[C@@H](CCC(O)=O)C(O)=O	3148.6	Standard polar	33892256
Isovalerylglutamic acid	CC(C)CC(=O)N[C@@H](CCC(O)=O)C(O)=O	1671.6	Standard non polar	33892256
Isovalerylglutamic acid	CC(C)CC(=O)N[C@@H](CCC(O)=O)C(O)=O	1936.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isovalerylglutamic acid,1TMS,isomer #1	CC(C)CC(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O	1909.6	Semi standard non polar	33892256
Isovalerylglutamic acid,1TMS,isomer #2	CC(C)CC(=O)N[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C	1901.8	Semi standard non polar	33892256
Isovalerylglutamic acid,1TMS,isomer #3	CC(C)CC(=O)N([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C	1905.1	Semi standard non polar	33892256
Isovalerylglutamic acid,2TMS,isomer #1	CC(C)CC(=O)N[C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1971.9	Semi standard non polar	33892256
Isovalerylglutamic acid,2TMS,isomer #2	CC(C)CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O)[Si](C)(C)C	1945.3	Semi standard non polar	33892256
Isovalerylglutamic acid,2TMS,isomer #3	CC(C)CC(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1950.4	Semi standard non polar	33892256
Isovalerylglutamic acid,3TMS,isomer #1	CC(C)CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1981.2	Semi standard non polar	33892256
Isovalerylglutamic acid,3TMS,isomer #1	CC(C)CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	1971.5	Standard non polar	33892256
Isovalerylglutamic acid,3TMS,isomer #1	CC(C)CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)[Si](C)(C)C	2099.4	Standard polar	33892256
Isovalerylglutamic acid,1TBDMS,isomer #1	CC(C)CC(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O	2152.4	Semi standard non polar	33892256
Isovalerylglutamic acid,1TBDMS,isomer #2	CC(C)CC(=O)N[C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C	2133.0	Semi standard non polar	33892256
Isovalerylglutamic acid,1TBDMS,isomer #3	CC(C)CC(=O)N([C@@H](CCC(=O)O)C(=O)O)[Si](C)(C)C(C)(C)C	2137.6	Semi standard non polar	33892256
Isovalerylglutamic acid,2TBDMS,isomer #1	CC(C)CC(=O)N[C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2402.7	Semi standard non polar	33892256
Isovalerylglutamic acid,2TBDMS,isomer #2	CC(C)CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)[Si](C)(C)C(C)(C)C	2409.7	Semi standard non polar	33892256
Isovalerylglutamic acid,2TBDMS,isomer #3	CC(C)CC(=O)N([C@@H](CCC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2402.7	Semi standard non polar	33892256
Isovalerylglutamic acid,3TBDMS,isomer #1	CC(C)CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2619.2	Semi standard non polar	33892256
Isovalerylglutamic acid,3TBDMS,isomer #1	CC(C)CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2532.3	Standard non polar	33892256
Isovalerylglutamic acid,3TBDMS,isomer #1	CC(C)CC(=O)N([C@@H](CCC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2519.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000l-9710000000-d968d94d4e1a6375e82b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00du-9123000000-9bfe7fee7822684dd801	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isovalerylglutamic acid GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isovalerylglutamic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-001j-1910000000-19ae59a8eb59a6c5dcf6	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isovalerylglutamic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-053r-9200000000-cc34006618257f6ea5b7	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isovalerylglutamic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-0a59-9000000000-3e27a676a2a4411c2829	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 10V, Positive-QTOF	splash10-03e9-2690000000-c94698b4419e50280bab	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 20V, Positive-QTOF	splash10-0zgr-5910000000-83e9ceaf3666b8af59e4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 40V, Positive-QTOF	splash10-0a4i-9300000000-487a10e7bb58ff39e503	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 10V, Negative-QTOF	splash10-001i-0390000000-8860fc75938c87bad1e0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 20V, Negative-QTOF	splash10-0gx9-2930000000-49505f61212051cf6fb5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 40V, Negative-QTOF	splash10-0zi3-9700000000-b36d32bd2df0b4eff525	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 10V, Positive-QTOF	splash10-000t-0940000000-f72f7d92a512f7367827	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 20V, Positive-QTOF	splash10-0f89-3900000000-3853c91ba592f8db62da	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 40V, Positive-QTOF	splash10-052u-9200000000-6d93f6efacf39fadd847	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 10V, Negative-QTOF	splash10-003r-0790000000-d24080c90f131f16a12d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 20V, Negative-QTOF	splash10-0ufs-0900000000-74ffc458766b51f8c074	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isovalerylglutamic acid 40V, Negative-QTOF	splash10-0udl-5900000000-c0aa356dc6adf7a53796	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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 ]

Showing metabocard for Isovalerylglutamic acid (HMDB0000726)

MOL for HMDB0000726 (Isovalerylglutamic acid)

3D MOL for HMDB0000726 (Isovalerylglutamic acid)

3D SDF for HMDB0000726 (Isovalerylglutamic acid)

3D-SDF for HMDB0000726 (Isovalerylglutamic acid)

PDB for HMDB0000726 (Isovalerylglutamic acid)

3D PDB for HMDB0000726 (Isovalerylglutamic acid)

SMILES for HMDB0000726 (Isovalerylglutamic acid)

INCHI for HMDB0000726 (Isovalerylglutamic acid)

Structure for HMDB0000726 (Isovalerylglutamic acid)

3D Structure for HMDB0000726 (Isovalerylglutamic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra