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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 09:20:02 UTC

Update Date

2021-09-24 09:20:02 UTC

HMDB ID

HMDB0304378

Secondary Accession Numbers

None

Metabolite Identification

Common Name

indole-3-acetyl-alanine

Description

Indole-3-acetyl-alanine is also known as iaa-ala. Indole-3-acetyl-alanine is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Indole-3-acetyl-alanine can be found in a number of food items such as yellow pond-lily, bean, black cabbage, and italian sweet red pepper, which makes indole-3-acetyl-alanine a potential biomarker for the consumption of these food products.

Structure

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

HMDB0304378
     RDKit          3D
indole-3-acetyl-alanine
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.1106   -0.7082    0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5475   -0.4671   -0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2842   -0.0796   -0.6669 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9642    0.3722   -0.7268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4299    1.2371   -1.2896 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2017   -0.6120    0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9985   -0.1828    0.6503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2055    0.3045    1.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3527    0.7368    2.2313 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0872    0.5903    1.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4050    0.8976    0.8048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8601    0.5441   -0.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0711   -0.0409   -1.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7546   -0.3198   -1.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2298    0.0010    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6931    0.2126   -1.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6009    1.3593   -1.7568 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8255   -0.5758   -1.4922 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.3092   -1.0405    1.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8828   -1.4853    0.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6244    0.2034    1.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5947   -1.5034   -1.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6990    1.1157   -1.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0643   -1.4798   -0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552   -1.0965    0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3387    0.3081    2.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8290    1.1599    3.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0744    1.3820    1.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9231    0.7270   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4968   -0.2541   -2.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0605   -0.7368   -1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  2 16  1  0
 16 17  2  0
 16 18  1  0
 15  7  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
M  CHG  1  18  -1
M  END


  Mrv1533005141513002D          

 18 19  0  0  0  0            999 V2000
    0.4542   -5.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -5.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2602   -4.6280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9747   -5.0405    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.2602   -3.8030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1687   -4.6280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832   -5.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5977   -4.6280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3121   -5.0405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0658   -4.7049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3207   -3.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1277   -3.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6798   -4.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4248   -5.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6178   -5.3180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2053   -6.0325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3984   -5.8610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8832   -5.8655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 10 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  9 17  2  0  0  0  0
  7 18  2  0  0  0  0
M  CHG  1   4  -1
M  END
> <DATABASE_ID>
HMDB0304378

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(NC(=O)CC1=CNC2=C1C=CC=C2)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2O3/c1-8(13(17)18)15-12(16)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7-8,14H,6H2,1H3,(H,15,16)(H,17,18)/p-1

> <INCHI_KEY>
FBDCJLXTUCMFLF-UHFFFAOYSA-M

> <FORMULA>
C13H13N2O3

> <MOLECULAR_WEIGHT>
245.259

> <EXACT_MASS>
245.093165867

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.8685587321358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[2-(1H-indol-3-yl)acetamido]propanoate

> <ALOGPS_LOGP>
1.19

> <JCHEM_LOGP>
1.173237101

> <ALOGPS_LOGS>
-2.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.432263715984405

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.053593121209233

> <JCHEM_PKA_STRONGEST_BASIC>
-2.779100963797938

> <JCHEM_POLAR_SURFACE_AREA>
85.01999999999998

> <JCHEM_REFRACTIVITY>
76.58660000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.74e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[2-(1H-indol-3-yl)acetamido]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304378
     RDKit          3D
indole-3-acetyl-alanine
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.1106   -0.7082    0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5475   -0.4671   -0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2842   -0.0796   -0.6669 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9642    0.3722   -0.7268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4299    1.2371   -1.2896 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2017   -0.6120    0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9985   -0.1828    0.6503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2055    0.3045    1.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3527    0.7368    2.2313 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0872    0.5903    1.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4050    0.8976    0.8048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8601    0.5441   -0.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0711   -0.0409   -1.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7546   -0.3198   -1.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2298    0.0010    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6931    0.2126   -1.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6009    1.3593   -1.7568 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8255   -0.5758   -1.4922 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.3092   -1.0405    1.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8828   -1.4853    0.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6244    0.2034    1.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5947   -1.5034   -1.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6990    1.1157   -1.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0643   -1.4798   -0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552   -1.0965    0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3387    0.3081    2.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8290    1.1599    3.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0744    1.3820    1.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9231    0.7270   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4968   -0.2541   -2.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0605   -0.7368   -1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  2 16  1  0
 16 17  2  0
 16 18  1  0
 15  7  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
M  CHG  1  18  -1
M  END

HEADER    PROTEIN                                 14-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-15         0                                  
HETATM    1  C   UNK     0       0.848 -10.949   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.848  -9.409   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.486  -8.639   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.819  -9.409   0.000  0.00  0.00           O-1
HETATM    5  O   UNK     0      -0.486  -7.099   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       2.182  -8.639   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.515  -9.409   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.849  -8.639   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.183  -9.409   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.590  -8.783   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.065  -7.318   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.572  -6.998   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.602  -8.142   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.126  -9.607   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.620  -9.927   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       7.850 -11.261   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0       6.344 -10.940   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.515 -10.949   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16    9                                                       
CONECT   18    7                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0304378
HETATM    1  C1  UNL     1       4.111  -0.708   0.706  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.547  -0.467  -0.645  1.00  0.00           C  
HETATM    3  N1  UNL     1       2.284  -0.080  -0.667  1.00  0.00           N  
HETATM    4  C3  UNL     1       0.964   0.372  -0.727  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.430   1.237  -1.290  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.202  -0.612   0.225  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.999  -0.183   0.650  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.206   0.304   1.978  1.00  0.00           C  
HETATM    9  N2  UNL     1      -2.353   0.737   2.231  1.00  0.00           N  
HETATM   10  C7  UNL     1      -3.087   0.590   1.049  1.00  0.00           C  
HETATM   11  C8  UNL     1      -4.405   0.898   0.805  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.860   0.544  -0.492  1.00  0.00           C  
HETATM   13  C10 UNL     1      -4.071  -0.041  -1.443  1.00  0.00           C  
HETATM   14  C11 UNL     1      -2.755  -0.320  -1.169  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.230   0.001   0.102  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.693   0.213  -1.358  1.00  0.00           C  
HETATM   17  O2  UNL     1       4.601   1.359  -1.757  1.00  0.00           O  
HETATM   18  O3  UNL     1       5.826  -0.576  -1.492  1.00  0.00           O1-
HETATM   19  H1  UNL     1       3.309  -1.041   1.417  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.883  -1.485   0.632  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.624   0.203   1.052  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.595  -1.503  -1.249  1.00  0.00           H  
HETATM   23  H5  UNL     1       2.699   1.116  -1.290  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.064  -1.480  -0.582  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.855  -1.096   0.947  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.339   0.308   2.728  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.829   1.160   3.065  1.00  0.00           H  
HETATM   28  H10 UNL     1      -5.074   1.382   1.524  1.00  0.00           H  
HETATM   29  H11 UNL     1      -5.923   0.727  -0.658  1.00  0.00           H  
HETATM   30  H12 UNL     1      -4.497  -0.254  -2.405  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.060  -0.737  -1.887  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   16   22
CONECT    3    4   23
CONECT    4    5    5    6
CONECT    6    7   24   25
CONECT    7    8    8   15
CONECT    8    9   26
CONECT    9   10   27
CONECT   10   11   11   15
CONECT   11   12   28
CONECT   12   13   13   29
CONECT   13   14   30
CONECT   14   15   15   31
CONECT   16   17   17   18
END

HMDB0304378
     RDKit          3D
indole-3-acetyl-alanine
 31 32  0  0  0  0  0  0  0  0999 V2000
    4.1106   -0.7082    0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5475   -0.4671   -0.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2842   -0.0796   -0.6669 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9642    0.3722   -0.7268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4299    1.2371   -1.2896 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2017   -0.6120    0.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9985   -0.1828    0.6503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2055    0.3045    1.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3527    0.7368    2.2313 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0872    0.5903    1.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4050    0.8976    0.8048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8601    0.5441   -0.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0711   -0.0409   -1.4433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7546   -0.3198   -1.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2298    0.0010    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6931    0.2126   -1.3575 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6009    1.3593   -1.7568 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8255   -0.5758   -1.4922 O   0  0  0  0  0  1  0  0  0  0  0  0
    3.3092   -1.0405    1.4175 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8828   -1.4853    0.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6244    0.2034    1.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5947   -1.5034   -1.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6990    1.1157   -1.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0643   -1.4798   -0.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8552   -1.0965    0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3387    0.3081    2.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8290    1.1599    3.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0744    1.3820    1.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9231    0.7270   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4968   -0.2541   -2.4053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0605   -0.7368   -1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  2 16  1  0
 16 17  2  0
 16 18  1  0
 15  7  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
M  CHG  1  18  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(1-Carboxyethyl)-2-(1H-indol-3-yl)ethanecarboximidic acid	Generator
Indole-3-acetyl-ala	MetaCyc
IAA-ala	MetaCyc

Chemical Formula

C₁₃H₁₃N₂O₃

Average Molecular Weight

245.259

Monoisotopic Molecular Weight

245.093165867

IUPAC Name

2-[2-(1H-indol-3-yl)acetamido]propanoate

Traditional Name

2-[2-(1H-indol-3-yl)acetamido]propanoate

CAS Registry Number

Not Available

SMILES

CC(NC(=O)CC1=CNC2=C1C=CC=C2)C([O-])=O

InChI Identifier

InChI=1S/C13H14N2O3/c1-8(13(17)18)15-12(16)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7-8,14H,6H2,1H3,(H,15,16)(H,17,18)/p-1

InChI Key

FBDCJLXTUCMFLF-UHFFFAOYSA-M

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Alanine or derivatives
3-alkylindole
Indole
Indole or derivatives
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Secondary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Carboxylic acid
Organoheterocyclic compound
Azacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (INDOLE-3-ACETYL-ALA )

Ontology

Not Available

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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
logP	1.19	ALOGPS
logP	1.17	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.05	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.02 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.59 m³·mol⁻¹	ChemAxon
Polarizability	24.87 Å³	ChemAxon
Number of Rings	2	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
AllCCS	[M+H]+	156.195	32859911
AllCCS	[M+H-H2O]+	152.488	32859911
AllCCS	[M+Na]+	160.627	32859911
AllCCS	[M+NH4]+	159.637	32859911
AllCCS	[M-H]-	156.919	32859911
AllCCS	[M+Na-2H]-	156.817	32859911
AllCCS	[M+HCOO]-	156.814	32859911
DeepCCS	[M+H]+	146.557	30932474
DeepCCS	[M-H]-	144.129	30932474
DeepCCS	[M-2H]-	178.768	30932474
DeepCCS	[M+Na]+	154.721	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
indole-3-acetyl-alanine,1TMS,isomer #1	CC(C(=O)[O-])N(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C	2353.3	Semi standard non polar	33892256
indole-3-acetyl-alanine,1TMS,isomer #1	CC(C(=O)[O-])N(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C	2293.1	Standard non polar	33892256
indole-3-acetyl-alanine,1TMS,isomer #1	CC(C(=O)[O-])N(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C	3023.7	Standard polar	33892256
indole-3-acetyl-alanine,1TMS,isomer #2	CC(NC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)[O-]	2360.5	Semi standard non polar	33892256
indole-3-acetyl-alanine,1TMS,isomer #2	CC(NC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)[O-]	2308.4	Standard non polar	33892256
indole-3-acetyl-alanine,1TMS,isomer #2	CC(NC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)C(=O)[O-]	3029.3	Standard polar	33892256
indole-3-acetyl-alanine,2TMS,isomer #1	CC(C(=O)[O-])N(C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2346.2	Semi standard non polar	33892256
indole-3-acetyl-alanine,2TMS,isomer #1	CC(C(=O)[O-])N(C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2364.5	Standard non polar	33892256
indole-3-acetyl-alanine,2TMS,isomer #1	CC(C(=O)[O-])N(C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2732.6	Standard polar	33892256
indole-3-acetyl-alanine,1TBDMS,isomer #1	CC(C(=O)[O-])N(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2608.0	Semi standard non polar	33892256
indole-3-acetyl-alanine,1TBDMS,isomer #1	CC(C(=O)[O-])N(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2514.4	Standard non polar	33892256
indole-3-acetyl-alanine,1TBDMS,isomer #1	CC(C(=O)[O-])N(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3052.6	Standard polar	33892256
indole-3-acetyl-alanine,1TBDMS,isomer #2	CC(NC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)[O-]	2586.4	Semi standard non polar	33892256
indole-3-acetyl-alanine,1TBDMS,isomer #2	CC(NC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)[O-]	2503.3	Standard non polar	33892256
indole-3-acetyl-alanine,1TBDMS,isomer #2	CC(NC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)C(=O)[O-]	3066.8	Standard polar	33892256
indole-3-acetyl-alanine,2TBDMS,isomer #1	CC(C(=O)[O-])N(C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2795.2	Semi standard non polar	33892256
indole-3-acetyl-alanine,2TBDMS,isomer #1	CC(C(=O)[O-])N(C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2791.2	Standard non polar	33892256
indole-3-acetyl-alanine,2TBDMS,isomer #1	CC(C(=O)[O-])N(C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2891.4	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - indole-3-acetyl-alanine 10V, Negative-QTOF	splash10-0002-0090000000-45627534d42d5faf1f56	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - indole-3-acetyl-alanine 20V, Negative-QTOF	splash10-0fg2-6790000000-68dc784ba12e19aca751	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - indole-3-acetyl-alanine 40V, Negative-QTOF	splash10-01bi-9500000000-2b775acd160e6b5e1c2a	2019-02-23	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

FDB030922

KNApSAcK ID

Not Available

Chemspider ID

24784720

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Not Available

Showing metabocard for indole-3-acetyl-alanine (HMDB0304378)

MOL for HMDB0304378 (indole-3-acetyl-alanine)

3D MOL for HMDB0304378 (indole-3-acetyl-alanine)

3D SDF for HMDB0304378 (indole-3-acetyl-alanine)

3D-SDF for HMDB0304378 (indole-3-acetyl-alanine)

PDB for HMDB0304378 (indole-3-acetyl-alanine)

3D PDB for HMDB0304378 (indole-3-acetyl-alanine)

SMILES for HMDB0304378 (indole-3-acetyl-alanine)

INCHI for HMDB0304378 (indole-3-acetyl-alanine)

Structure for HMDB0304378 (indole-3-acetyl-alanine)

3D Structure for HMDB0304378 (indole-3-acetyl-alanine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra