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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2020-06-04 21:44:49 UTC

Update Date

2022-09-22 18:34:33 UTC

HMDB ID

HMDB0240661

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Indole-3-acetylglycine

Description

Indole-3-acetylglycine also known as N-(3-indolylacetyl)glycine, 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. Indole-3-acetylglycine has been identified in urine (PMID: 31396400 ).

Structure

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

HMDB0240661
     RDKit          3D
Indole-3-acetylglycine
 29 30  0  0  0  0  0  0  0  0999 V2000
    3.5491    1.5675    1.9198 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0805    1.2916    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2431    1.9080    0.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4048    0.2754   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881   -0.2437    0.6028 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3801   -1.1955   -0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292   -1.5867   -1.2191 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1481   -1.7952    0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638   -1.4279   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7153   -2.1666   -1.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7578   -1.4842   -1.7864 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7784   -0.2779   -1.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6173    0.8088   -1.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4291    1.9330   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3842    1.9716    0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315    0.8998    0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7466   -0.2154   -0.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1175    1.4989    0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1296    0.7321   -0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1157   -0.5755   -0.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9531    0.1098    1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0124   -1.4455    1.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2673   -2.9190    0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4003   -3.1811   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4157   -1.8276   -2.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4445    0.8307   -1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0727    2.8077   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2412    2.8345    1.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6953    0.8723    1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  9  1  0
 17 12  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  8 22  1  0
  8 23  1  0
 10 24  1  0
 11 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
M  END


  Mrv1652306042023462D          

 17 18  0  0  0  0            999 V2000
   -2.0006    0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2556   -0.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7035   -1.1419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8965   -0.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7812    1.1419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1936    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6415   -0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1120    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0257    0.9703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8266   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5410    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5410    0.9749    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2556   -0.2626    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9700    0.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6846   -0.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6847   -1.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3991    0.1501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  1  0  0  0  0
 11 12  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240661

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)CNC(=O)CC1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H12N2O3/c15-11(14-7-12(16)17)5-8-6-13-10-4-2-1-3-9(8)10/h1-4,6,13H,5,7H2,(H,14,15)(H,16,17)

> <INCHI_KEY>
YDXXLJMIHMIOIF-UHFFFAOYSA-N

> <FORMULA>
C12H12N2O3

> <MOLECULAR_WEIGHT>
232.2353

> <EXACT_MASS>
232.08479226

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
23.21812245079512

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.15

> <JCHEM_LOGP>
0.6044728586666668

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.58411739863908

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.035278644955276

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9835003881894058

> <JCHEM_POLAR_SURFACE_AREA>
82.19

> <JCHEM_REFRACTIVITY>
61.25560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.64e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240661
     RDKit          3D
Indole-3-acetylglycine
 29 30  0  0  0  0  0  0  0  0999 V2000
    3.5491    1.5675    1.9198 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0805    1.2916    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2431    1.9080    0.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4048    0.2754   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881   -0.2437    0.6028 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3801   -1.1955   -0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292   -1.5867   -1.2191 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1481   -1.7952    0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638   -1.4279   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7153   -2.1666   -1.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7578   -1.4842   -1.7864 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7784   -0.2779   -1.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6173    0.8088   -1.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4291    1.9330   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3842    1.9716    0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315    0.8998    0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7466   -0.2154   -0.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1175    1.4989    0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1296    0.7321   -0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1157   -0.5755   -0.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9531    0.1098    1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0124   -1.4455    1.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2673   -2.9190    0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4003   -3.1811   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4157   -1.8276   -2.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4445    0.8307   -1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0727    2.8077   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2412    2.8345    1.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6953    0.8723    1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  9  1  0
 17 12  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  8 22  1  0
  8 23  1  0
 10 24  1  0
 11 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
M  END

HEADER    PROTEIN                                 04-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUN-20         0                                  
HETATM    1  C   UNK     0      -3.735   0.478   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.210  -0.987   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.180  -2.132   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.673  -1.812   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -1.458   2.132   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -2.228   0.798   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.198  -0.347   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.209   0.280   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.048   1.811   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.543  -0.490   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.877   0.280   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.877   1.820   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0       4.210  -0.490   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       5.544   0.280   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.878  -0.490   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.878  -2.030   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.212   0.280   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   11                                                       
CONECT   11   10   13   12                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0240661
HETATM    1  O1  UNL     1       3.549   1.567   1.920  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.080   1.292   0.806  1.00  0.00           C  
HETATM    3  O2  UNL     1       5.243   1.908   0.389  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.405   0.275  -0.041  1.00  0.00           C  
HETATM    5  N1  UNL     1       2.188  -0.244   0.603  1.00  0.00           N  
HETATM    6  C3  UNL     1       1.380  -1.196  -0.048  1.00  0.00           C  
HETATM    7  O3  UNL     1       1.729  -1.587  -1.219  1.00  0.00           O  
HETATM    8  C4  UNL     1       0.148  -1.795   0.498  1.00  0.00           C  
HETATM    9  C5  UNL     1      -1.064  -1.428  -0.313  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.715  -2.167  -1.273  1.00  0.00           C  
HETATM   11  N2  UNL     1      -2.758  -1.484  -1.786  1.00  0.00           N  
HETATM   12  C7  UNL     1      -2.778  -0.278  -1.142  1.00  0.00           C  
HETATM   13  C8  UNL     1      -3.617   0.809  -1.248  1.00  0.00           C  
HETATM   14  C9  UNL     1      -3.429   1.933  -0.456  1.00  0.00           C  
HETATM   15  C10 UNL     1      -2.384   1.972   0.455  1.00  0.00           C  
HETATM   16  C11 UNL     1      -1.531   0.900   0.580  1.00  0.00           C  
HETATM   17  C12 UNL     1      -1.747  -0.215  -0.228  1.00  0.00           C  
HETATM   18  H1  UNL     1       6.118   1.499   0.700  1.00  0.00           H  
HETATM   19  H2  UNL     1       3.130   0.732  -0.990  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.116  -0.575  -0.249  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.953   0.110   1.543  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.012  -1.445   1.531  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.267  -2.919   0.509  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.400  -3.181  -1.562  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.416  -1.828  -2.535  1.00  0.00           H  
HETATM   26  H9  UNL     1      -4.445   0.831  -1.944  1.00  0.00           H  
HETATM   27  H10 UNL     1      -4.073   2.808  -0.511  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.241   2.834   1.058  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.695   0.872   1.281  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   18
CONECT    4    5   19   20
CONECT    5    6   21
CONECT    6    7    7    8
CONECT    8    9   22   23
CONECT    9   10   10   17
CONECT   10   11   24
CONECT   11   12   25
CONECT   12   13   13   17
CONECT   13   14   26
CONECT   14   15   15   27
CONECT   15   16   28
CONECT   16   17   17   29
END

HMDB0240661
     RDKit          3D
Indole-3-acetylglycine
 29 30  0  0  0  0  0  0  0  0999 V2000
    3.5491    1.5675    1.9198 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0805    1.2916    0.8061 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2431    1.9080    0.3893 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4048    0.2754   -0.0412 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1881   -0.2437    0.6028 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3801   -1.1955   -0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7292   -1.5867   -1.2191 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1481   -1.7952    0.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0638   -1.4279   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7153   -2.1666   -1.2731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7578   -1.4842   -1.7864 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7784   -0.2779   -1.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6173    0.8088   -1.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4291    1.9330   -0.4563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3842    1.9716    0.4550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315    0.8998    0.5804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7466   -0.2154   -0.2283 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1175    1.4989    0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1296    0.7321   -0.9902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1157   -0.5755   -0.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9531    0.1098    1.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0124   -1.4455    1.5306 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2673   -2.9190    0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4003   -3.1811   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4157   -1.8276   -2.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4445    0.8307   -1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0727    2.8077   -0.5107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2412    2.8345    1.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6953    0.8723    1.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17  9  1  0
 17 12  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  8 22  1  0
  8 23  1  0
 10 24  1  0
 11 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-(1H-indol-3-Ylacetyl)glycine	ChEBI
N-Indoleacetylglycine	ChEBI
2-[2-(1H-Indol-3-yl)acetamido]acetic acid	HMDB
2-[[2-(1H-Indol-3-yl)acetyl]amino]acetic acid	HMDB
Indole-3-acetylglycine	HMDB
Indoleacetylglycine	HMDB
N-(3-Indolylacetyl)glycine	HMDB
N-[2-(1H-Indol-3-yl)acetyl]glycine	HMDB

Chemical Formula

C₁₂H₁₂N₂O₃

Average Molecular Weight

232.2353

Monoisotopic Molecular Weight

232.08479226

IUPAC Name

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

Traditional Name

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

CAS Registry Number

13113-08-1

SMILES

OC(=O)CNC(=O)CC1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1S/C12H12N2O3/c15-11(14-7-12(16)17)5-8-6-13-10-4-2-1-3-9(8)10/h1-4,6,13H,5,7H2,(H,14,15)(H,16,17)

InChI Key

YDXXLJMIHMIOIF-UHFFFAOYSA-N

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 31396400)

Source

Exogenous

Exogenous (HMDB: HMDB0240661)

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	1.15	ALOGPS
logP	0.6	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.04	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.19 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	61.26 m³·mol⁻¹	ChemAxon
Polarizability	23.22 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
DeepCCS	[M+H]+	145.495	30932474
DeepCCS	[M-H]-	143.11	30932474
DeepCCS	[M-2H]-	176.985	30932474
DeepCCS	[M+Na]+	151.772	30932474
AllCCS	[M+H]+	151.4	32859911
AllCCS	[M+H-H2O]+	147.6	32859911
AllCCS	[M+NH4]+	154.9	32859911
AllCCS	[M+Na]+	155.9	32859911
AllCCS	[M-H]-	154.0	32859911
AllCCS	[M+Na-2H]-	153.9	32859911
AllCCS	[M+HCOO]-	154.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	4.48 minutes	32390414
Predicted by Siyang on May 30, 2022	10.1932 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.3 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1430.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	284.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	112.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	169.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	142.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	305.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	314.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	113.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	727.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	342.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1109.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	289.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	246.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	379.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	189.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	119.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Indole-3-acetylglycine	OC(=O)CNC(=O)CC1=CNC2=C1C=CC=C2	3912.8	Standard polar	33892256
Indole-3-acetylglycine	OC(=O)CNC(=O)CC1=CNC2=C1C=CC=C2	2052.7	Standard non polar	33892256
Indole-3-acetylglycine	OC(=O)CNC(=O)CC1=CNC2=C1C=CC=C2	2575.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Indole-3-acetylglycine,1TMS,isomer #1	C[Si](C)(C)OC(=O)CNC(=O)CC1=C[NH]C2=CC=CC=C12	2508.9	Semi standard non polar	33892256
Indole-3-acetylglycine,1TMS,isomer #2	C[Si](C)(C)N(CC(=O)O)C(=O)CC1=C[NH]C2=CC=CC=C12	2512.8	Semi standard non polar	33892256
Indole-3-acetylglycine,1TMS,isomer #3	C[Si](C)(C)N1C=C(CC(=O)NCC(=O)O)C2=CC=CC=C21	2528.0	Semi standard non polar	33892256
Indole-3-acetylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C	2492.7	Semi standard non polar	33892256
Indole-3-acetylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C	2448.2	Standard non polar	33892256
Indole-3-acetylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C	2930.1	Standard polar	33892256
Indole-3-acetylglycine,2TMS,isomer #2	C[Si](C)(C)OC(=O)CNC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2488.1	Semi standard non polar	33892256
Indole-3-acetylglycine,2TMS,isomer #2	C[Si](C)(C)OC(=O)CNC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2392.9	Standard non polar	33892256
Indole-3-acetylglycine,2TMS,isomer #2	C[Si](C)(C)OC(=O)CNC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2883.4	Standard polar	33892256
Indole-3-acetylglycine,2TMS,isomer #3	C[Si](C)(C)N(CC(=O)O)C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2505.8	Semi standard non polar	33892256
Indole-3-acetylglycine,2TMS,isomer #3	C[Si](C)(C)N(CC(=O)O)C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2485.7	Standard non polar	33892256
Indole-3-acetylglycine,2TMS,isomer #3	C[Si](C)(C)N(CC(=O)O)C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2962.4	Standard polar	33892256
Indole-3-acetylglycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2481.9	Semi standard non polar	33892256
Indole-3-acetylglycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2497.3	Standard non polar	33892256
Indole-3-acetylglycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN(C(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2714.2	Standard polar	33892256
Indole-3-acetylglycine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)CC1=C[NH]C2=CC=CC=C12	2793.8	Semi standard non polar	33892256
Indole-3-acetylglycine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)CC1=C[NH]C2=CC=CC=C12	2779.5	Semi standard non polar	33892256
Indole-3-acetylglycine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=C(CC(=O)NCC(=O)O)C2=CC=CC=C21	2767.0	Semi standard non polar	33892256
Indole-3-acetylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2986.4	Semi standard non polar	33892256
Indole-3-acetylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2877.0	Standard non polar	33892256
Indole-3-acetylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3063.3	Standard polar	33892256
Indole-3-acetylglycine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2959.7	Semi standard non polar	33892256
Indole-3-acetylglycine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2819.9	Standard non polar	33892256
Indole-3-acetylglycine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CNC(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	3017.2	Standard polar	33892256
Indole-3-acetylglycine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2955.8	Semi standard non polar	33892256
Indole-3-acetylglycine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2884.2	Standard non polar	33892256
Indole-3-acetylglycine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CC(=O)O)C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	3080.9	Standard polar	33892256
Indole-3-acetylglycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3118.5	Semi standard non polar	33892256
Indole-3-acetylglycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	3090.0	Standard non polar	33892256
Indole-3-acetylglycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN(C(=O)CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2980.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Indole-3-acetylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4940000000-2c6689ca8c94fce67cdf	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indole-3-acetylglycine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetylglycine 10V, Positive-QTOF	splash10-00e9-9350000000-adc6e0e4dbb74ff02a0f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetylglycine 20V, Positive-QTOF	splash10-00fr-9300000000-b89a0e374f736ec1d22f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetylglycine 40V, Positive-QTOF	splash10-00c0-9300000000-4d6a52fe9ef347ccb264	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetylglycine 10V, Negative-QTOF	splash10-001i-0390000000-5fc9d4f087b67215ec80	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetylglycine 20V, Negative-QTOF	splash10-001i-4960000000-7d65845431b48c7f6bea	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetylglycine 40V, Negative-QTOF	splash10-01b9-8900000000-70f20f051ef685593fdf	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetylglycine 10V, Negative-QTOF	splash10-05o0-1930000000-5ed1994e6ff7c3c90cc0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetylglycine 20V, Negative-QTOF	splash10-014i-1900000000-9983c157c88aaee17d70	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetylglycine 40V, Negative-QTOF	splash10-066r-8900000000-53c9fadbd6a8af3a5c8d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetylglycine 10V, Positive-QTOF	splash10-001i-0940000000-fd52f2371126f6f58f58	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetylglycine 20V, Positive-QTOF	splash10-001i-0900000000-f80374c87cd6ea03aea3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetylglycine 40V, Positive-QTOF	splash10-001i-0900000000-0d13c78e93faa52ddc5a	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	31396400	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

393944

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

90332

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

Zarei I, Oppel RC, Borresen EC, Brown RJ, Ryan EP: Modulation of plasma and urine metabolome in colorectal cancer survivors consuming rice bran. Integr Food Nutr Metab. 2019 May;6(3). doi: 10.15761/IFNM.1000252. Epub 2019 Apr 5. [PubMed:31396400 ]

Showing metabocard for Indole-3-acetylglycine (HMDB0240661)

MOL for HMDB0240661 (Indole-3-acetylglycine)

3D MOL for HMDB0240661 (Indole-3-acetylglycine)

3D SDF for HMDB0240661 (Indole-3-acetylglycine)

3D-SDF for HMDB0240661 (Indole-3-acetylglycine)

PDB for HMDB0240661 (Indole-3-acetylglycine)

3D PDB for HMDB0240661 (Indole-3-acetylglycine)

SMILES for HMDB0240661 (Indole-3-acetylglycine)

INCHI for HMDB0240661 (Indole-3-acetylglycine)

Structure for HMDB0240661 (Indole-3-acetylglycine)

3D Structure for HMDB0240661 (Indole-3-acetylglycine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra