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Showing metabocard for Valylglycine (HMDB0029127)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:03:48 UTC
Update Date2023-02-21 17:18:37 UTC
HMDB IDHMDB0029127
Secondary Accession Numbers
  • HMDB29127
Metabolite Identification
Common NameValylglycine
DescriptionValylglycine is a dipeptide composed of valine and glycine. It is an incomplete breakdown product of protein digestion or protein catabolism. Dipeptides are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Some dipeptides are known to have physiological or cell-signalling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.
Structure
Data?1676999917
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0029127 (Valylglycine)


  Mrv1652304062014252D          

 12 11  0  0  0  0            999 V2000
10027.991310028.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10028.708710028.5767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10029.423410028.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10030.138110028.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10030.852810028.1646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10030.138110029.4018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10027.277610028.5767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10026.561910028.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10025.848210028.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10026.561910027.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10027.277610029.4018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10027.991310027.3393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 12  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  6  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
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3D MOL for HMDB0029127 (Valylglycine)

HMDB0029127
     RDKit          3D
Valylglycine
 26 25  0  0  0  0  0  0  0  0999 V2000
   -2.9005   -1.0369   -0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6113   -0.2727   -0.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9303    1.1926   -0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7224   -0.5889    0.7819 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3290   -0.2140    2.0220 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6219   -0.0045    0.6506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0700    0.7176    1.5819 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4175   -0.2379   -0.4984 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7559    0.3641   -0.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5399   -0.1472    0.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1046   -0.9478    1.4107 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8503    0.2812    0.6766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3654   -1.2774   -1.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6277   -0.4733    0.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7489   -2.0171    0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1026   -0.6371   -1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6763    1.5352   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0013    1.4230   -0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3594    1.7752    0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6059   -1.7058    0.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681   -0.2869    1.9921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0138    0.6814    2.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361   -0.8316   -1.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6223    1.4637   -0.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2088    0.0659   -1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1356    1.1790    0.3116 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
  4  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
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  1
  5 21  1  0
  5 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 12 26  1  0
M  END
Download

3D SDF for HMDB0029127 (Valylglycine)


  Mrv1652304062014252D          

 12 11  0  0  0  0            999 V2000
10027.991310028.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10028.708710028.5767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10029.423410028.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10030.138110028.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10030.852810028.1646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10030.138110029.4018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10027.277610028.5767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10026.561910028.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10025.848210028.5767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10026.561910027.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10027.277610029.4018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10027.991310027.3393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 12  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  6  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029127

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H14N2O3/c1-4(2)6(8)7(12)9-3-5(10)11/h4,6H,3,8H2,1-2H3,(H,9,12)(H,10,11)/t6-/m0/s1

> <INCHI_KEY>
IOUPEELXVYPCPG-LURJTMIESA-N

> <FORMULA>
C7H14N2O3

> <MOLECULAR_WEIGHT>
174.2

> <EXACT_MASS>
174.100442319

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
17.70859814360833

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2S)-2-amino-3-methylbutanamido]acetic acid

> <ALOGPS_LOGP>
-2.46

> <JCHEM_LOGP>
-3.0611909888375113

> <ALOGPS_LOGS>
-0.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.491418912809078

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.865079118607637

> <JCHEM_PKA_STRONGEST_BASIC>
8.514789988849243

> <JCHEM_POLAR_SURFACE_AREA>
92.41999999999999

> <JCHEM_REFRACTIVITY>
42.2964

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.63e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S)-2-amino-3-methylbutanamido]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0029127 (Valylglycine)

HMDB0029127
     RDKit          3D
Valylglycine
 26 25  0  0  0  0  0  0  0  0999 V2000
   -2.9005   -1.0369   -0.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6113   -0.2727   -0.3976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9303    1.1926   -0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7224   -0.5889    0.7819 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3290   -0.2140    2.0220 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6219   -0.0045    0.6506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0700    0.7176    1.5819 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4175   -0.2379   -0.4984 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7559    0.3641   -0.5917 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5399   -0.1472    0.5458 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1046   -0.9478    1.4107 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8503    0.2812    0.6766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3654   -1.2774   -1.2275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6277   -0.4733    0.3969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7489   -2.0171    0.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1026   -0.6371   -1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6763    1.5352   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0013    1.4230   -0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3594    1.7752    0.2526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6059   -1.7058    0.7915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3681   -0.2869    1.9921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0138    0.6814    2.4108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0361   -0.8316   -1.2525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6223    1.4637   -0.5658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2088    0.0659   -1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1356    1.1790    0.3116 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
  4  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
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  1
  5 21  1  0
  5 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 12 26  1  0
M  END
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PDB for HMDB0029127 (Valylglycine)

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0    8718.9178719.241   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0    8720.2568720.010   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0    8721.5908719.241   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8722.9248720.010   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8724.2598719.241   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8722.9248721.550   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8717.5858720.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8716.2498719.241   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8714.9178720.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8716.2498717.700   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    8717.5858721.550   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0    8718.9178717.700   0.000  0.00  0.00           O+0
CONECT    1    2    7   12                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    1    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7                                                            
CONECT   12    1                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END
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3D PDB for HMDB0029127 (Valylglycine)

COMPND    HMDB0029127
HETATM    1  C1  UNL     1      -2.901  -1.037  -0.232  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.611  -0.273  -0.398  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.930   1.193  -0.499  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.722  -0.589   0.782  1.00  0.00           C  
HETATM    5  N1  UNL     1      -1.329  -0.214   2.022  1.00  0.00           N  
HETATM    6  C5  UNL     1       0.622  -0.004   0.651  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.070   0.718   1.582  1.00  0.00           O  
HETATM    8  N2  UNL     1       1.417  -0.238  -0.498  1.00  0.00           N  
HETATM    9  C6  UNL     1       2.756   0.364  -0.592  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.540  -0.147   0.546  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.105  -0.948   1.411  1.00  0.00           O  
HETATM   12  O3  UNL     1       4.850   0.281   0.677  1.00  0.00           O  
HETATM   13  H1  UNL     1      -3.365  -1.277  -1.228  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.628  -0.473   0.397  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.749  -2.017   0.275  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.103  -0.637  -1.312  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.676   1.535  -1.515  1.00  0.00           H  
HETATM   18  H6  UNL     1      -3.001   1.423  -0.341  1.00  0.00           H  
HETATM   19  H7  UNL     1      -1.359   1.775   0.253  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.606  -1.706   0.792  1.00  0.00           H  
HETATM   21  H9  UNL     1      -2.368  -0.287   1.992  1.00  0.00           H  
HETATM   22  H10 UNL     1      -1.014   0.681   2.411  1.00  0.00           H  
HETATM   23  H11 UNL     1       1.036  -0.832  -1.253  1.00  0.00           H  
HETATM   24  H12 UNL     1       2.622   1.464  -0.566  1.00  0.00           H  
HETATM   25  H13 UNL     1       3.209   0.066  -1.552  1.00  0.00           H  
HETATM   26  H14 UNL     1       5.136   1.179   0.312  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    4   16
CONECT    3   17   18   19
CONECT    4    5    6   20
CONECT    5   21   22
CONECT    6    7    7    8
CONECT    8    9   23
CONECT    9   10   24   25
CONECT   10   11   11   12
CONECT   12   26
END
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SMILES for HMDB0029127 (Valylglycine)

CC(C)[C@H](N)C(=O)NCC(O)=O
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INCHI for HMDB0029127 (Valylglycine)

InChI=1S/C7H14N2O3/c1-4(2)6(8)7(12)9-3-5(10)11/h4,6H,3,8H2,1-2H3,(H,9,12)(H,10,11)/t6-/m0/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
L-Val-glyChEBI
V-GChEBI
VGChEBI
L-ValylglycineHMDB
N-L-ValylglycineHMDB
N-ValylglycineHMDB
V-g DipeptideHMDB
VG DipeptideHMDB
Val-glyHMDB
Valine glycine dipeptideHMDB
Valine-glycine dipeptideHMDB
Valyl-glycineHMDB
ValylglycineChEBI
Chemical FormulaC7H14N2O3
Average Molecular Weight174.2
Monoisotopic Molecular Weight174.100442319
IUPAC Name2-[(2S)-2-amino-3-methylbutanamido]acetic acid
Traditional Name[(2S)-2-amino-3-methylbutanamido]acetic acid
CAS Registry Number686-43-1
SMILES
CC(C)[C@H](N)C(=O)NCC(O)=O
InChI Identifier
InChI=1S/C7H14N2O3/c1-4(2)6(8)7(12)9-3-5(10)11/h4,6H,3,8H2,1-2H3,(H,9,12)(H,10,11)/t6-/m0/s1
InChI KeyIOUPEELXVYPCPG-LURJTMIESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Valine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • Fatty acyl
  • Fatty amide
  • N-acyl-amine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Carboxylic acid salt
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Primary aliphatic amine
  • Organic zwitterion
  • Organic salt
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.06Extrapolated
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility26.3 g/LALOGPS
logP-2.5ALOGPS
logP-3.1ChemAxon
logS-0.82ALOGPS
pKa (Strongest Acidic)3.87ChemAxon
pKa (Strongest Basic)8.51ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.42 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity42.3 m³·mol⁻¹ChemAxon
Polarizability17.71 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+138.85430932474
DeepCCS[M-H]-135.70330932474
DeepCCS[M-2H]-172.58630932474
DeepCCS[M+Na]+148.12430932474

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.25 minutes32390414
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.04 minutes32390414
Predicted by Siyang on May 30, 20229.4424 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20227.72 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid280.4 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid700.2 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid271.5 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid65.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid162.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid48.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid277.5 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid250.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)568.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid599.8 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid118.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid778.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid166.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid177.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate468.1 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA418.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water218.0 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ValylglycineCC(C)[C@H](N)C(=O)NCC(O)=O2531.5Standard polar33892256
ValylglycineCC(C)[C@H](N)C(=O)NCC(O)=O1508.2Standard non polar33892256
ValylglycineCC(C)[C@H](N)C(=O)NCC(O)=O1651.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Valylglycine,1TMS,isomer #1CC(C)[C@H](N)C(=O)NCC(=O)O[Si](C)(C)C1652.7Semi standard non polar33892256
Valylglycine,1TMS,isomer #2CC(C)[C@H](N[Si](C)(C)C)C(=O)NCC(=O)O1660.1Semi standard non polar33892256
Valylglycine,1TMS,isomer #3CC(C)[C@H](N)C(=O)N(CC(=O)O)[Si](C)(C)C1646.7Semi standard non polar33892256
Valylglycine,2TMS,isomer #1CC(C)[C@H](N[Si](C)(C)C)C(=O)NCC(=O)O[Si](C)(C)C1715.1Semi standard non polar33892256
Valylglycine,2TMS,isomer #1CC(C)[C@H](N[Si](C)(C)C)C(=O)NCC(=O)O[Si](C)(C)C1676.8Standard non polar33892256
Valylglycine,2TMS,isomer #2CC(C)[C@H](N)C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1631.8Semi standard non polar33892256
Valylglycine,2TMS,isomer #2CC(C)[C@H](N)C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1721.2Standard non polar33892256
Valylglycine,2TMS,isomer #3CC(C)[C@@H](C(=O)NCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C1831.8Semi standard non polar33892256
Valylglycine,2TMS,isomer #3CC(C)[C@@H](C(=O)NCC(=O)O)N([Si](C)(C)C)[Si](C)(C)C1688.9Standard non polar33892256
Valylglycine,2TMS,isomer #4CC(C)[C@H](N[Si](C)(C)C)C(=O)N(CC(=O)O)[Si](C)(C)C1708.7Semi standard non polar33892256
Valylglycine,2TMS,isomer #4CC(C)[C@H](N[Si](C)(C)C)C(=O)N(CC(=O)O)[Si](C)(C)C1716.4Standard non polar33892256
Valylglycine,3TMS,isomer #1CC(C)[C@@H](C(=O)NCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1852.8Semi standard non polar33892256
Valylglycine,3TMS,isomer #1CC(C)[C@@H](C(=O)NCC(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1785.9Standard non polar33892256
Valylglycine,3TMS,isomer #2CC(C)[C@H](N[Si](C)(C)C)C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1719.8Semi standard non polar33892256
Valylglycine,3TMS,isomer #2CC(C)[C@H](N[Si](C)(C)C)C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C1759.4Standard non polar33892256
Valylglycine,3TMS,isomer #3CC(C)[C@@H](C(=O)N(CC(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1832.9Semi standard non polar33892256
Valylglycine,3TMS,isomer #3CC(C)[C@@H](C(=O)N(CC(=O)O)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1835.8Standard non polar33892256
Valylglycine,4TMS,isomer #1CC(C)[C@@H](C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1905.4Semi standard non polar33892256
Valylglycine,4TMS,isomer #1CC(C)[C@@H](C(=O)N(CC(=O)O[Si](C)(C)C)[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1892.5Standard non polar33892256
Valylglycine,1TBDMS,isomer #1CC(C)[C@H](N)C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C1905.3Semi standard non polar33892256
Valylglycine,1TBDMS,isomer #2CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)NCC(=O)O1914.0Semi standard non polar33892256
Valylglycine,1TBDMS,isomer #3CC(C)[C@H](N)C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C1876.4Semi standard non polar33892256
Valylglycine,2TBDMS,isomer #1CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C2148.1Semi standard non polar33892256
Valylglycine,2TBDMS,isomer #1CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C2076.8Standard non polar33892256
Valylglycine,2TBDMS,isomer #2CC(C)[C@H](N)C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2097.4Semi standard non polar33892256
Valylglycine,2TBDMS,isomer #2CC(C)[C@H](N)C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2131.2Standard non polar33892256
Valylglycine,2TBDMS,isomer #3CC(C)[C@@H](C(=O)NCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2282.6Semi standard non polar33892256
Valylglycine,2TBDMS,isomer #3CC(C)[C@@H](C(=O)NCC(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2098.8Standard non polar33892256
Valylglycine,2TBDMS,isomer #4CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C2160.5Semi standard non polar33892256
Valylglycine,2TBDMS,isomer #4CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C2101.4Standard non polar33892256
Valylglycine,3TBDMS,isomer #1CC(C)[C@@H](C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2510.5Semi standard non polar33892256
Valylglycine,3TBDMS,isomer #1CC(C)[C@@H](C(=O)NCC(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2364.0Standard non polar33892256
Valylglycine,3TBDMS,isomer #2CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2382.9Semi standard non polar33892256
Valylglycine,3TBDMS,isomer #2CC(C)[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2337.8Standard non polar33892256
Valylglycine,3TBDMS,isomer #3CC(C)[C@@H](C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2507.4Semi standard non polar33892256
Valylglycine,3TBDMS,isomer #3CC(C)[C@@H](C(=O)N(CC(=O)O)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2398.0Standard non polar33892256
Valylglycine,4TBDMS,isomer #1CC(C)[C@@H](C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2746.5Semi standard non polar33892256
Valylglycine,4TBDMS,isomer #1CC(C)[C@@H](C(=O)N(CC(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2622.6Standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112129
KNApSAcK IDNot Available
Chemspider ID5361214
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6993110
PDB IDNot Available
ChEBI ID73699
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gordon-Smith EC, Dacie JV, Blecher TE, French EA, Wiltshirre BG, Lehmann H: Haemoglobin Nottingham, beta FG 5 (98) valgly: a new unstable haemoglobin producing severe haemolysis. Proc R Soc Med. 1973 Jun;66(6):507-8. [PubMed:4781799 ]
  2. Kizer JS, Bateman RC Jr, Miller CR, Humm J, Busby WH Jr, Youngblood WW: Purification and characterization of a peptidyl glycine monooxygenase from porcine pituitary. Endocrinology. 1986 Jun;118(6):2262-7. [PubMed:3698913 ]
  3. D'Alagni M, Pispisa B: Effect of urea on the optical rotatory dispersion of diketopiperazines of L-serine, L-alanine, L-lysine, L-valine, and L-valylglycine. J Biol Chem. 1969 Nov 10;244(21):5843-8. [PubMed:5350939 ]