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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2007-04-12 20:13:16 UTC

Update Date

2022-09-22 18:35:07 UTC

HMDB ID

HMDB0006005

Secondary Accession Numbers

HMDB06005

Metabolite Identification

Common Name

Indolylacryloylglycine

Description

Indolylacryloylglycine, also known as Indolyl-3-acrylogylglycine or IAG, 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. Indolylacryloylglycine is synthesized from tryptophan via indoleacrylic acid (IAcrA) through the conjugation of glycine to IAcrA via endogenous enzymes such as glycine N-acyltransferase (PMID: 10707769 ). The IAcrA must be first conjugated to CoA for this reaction to occur. The indoleacrylic acid is typically produced via microbially derived commensal Peptostreptococcus species (PMID: 28704649 ). IAG is also directly produced by L-tryptophan via certain mammalian gut microbes containing the enzyme tryptophan ammonia lyase (PMID: 25961404 ). Tryptophan ammonia lyase (EC 4.3.1.31) catalyzes the reaction of L-tryptophan to directly produce indole-3-acrylic acid and ammonia. This enzyme was initially characterized from the bacterium Rubrivivax benzoatilyticus JA2 (PMID: 25961404 ). It requires no cofactors and acts on L-phenylalanine and L-glutamate with about 60% of the activity of L-tryptophan, and on L-tyrosine, glycine, and L-alanine with about 30% of the activity (PMID: 25961404 ). Overall, IAG is both a microbial-host co-metabolite and a pure microbial metabolite. IAG may be a biomarker for autism spectrum disorders (PMID: 11858215 , PMID: 14523330 , PMID: 19697973 ). It has been reported that urinary levels of IAG are much higher in autistic children than in controls. However, these findings are controversial and have not been reproduced consistently (PMID: 27569540 , PMID: 27879968 ). Elevated urinary Indolylacryloylglycine may also be a marker for gastroinstestinal dysfunction (PMID: 19697973 ). Urinary Indolylacryloylglycine has also been reported as a potential biomarker to distinguish high-grade bladder cancer from low-grade bladder cancer (PMID: 29451296 ). Indolylacryloylglycine has been detected, but not quantified in, several different foods, such as chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and milk (cow). This could make indolylacryloylglycine a potential biomarker for the consumption of these foods.

Structure

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

HMDB0006005
     RDKit          3D
Indolylacryloylglycine
 30 31  0  0  0  0  0  0  0  0999 V2000
    5.9702    1.8248   -0.8946 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7944    1.3457   -0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0092    1.1882   -1.9094 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2704    0.9603    0.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9455    0.4563    0.4197 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -0.7322    0.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5817   -1.6897   -0.0413 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2172   -1.1420    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2017   -0.3072    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1907   -0.7508    0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6361   -2.0340   -0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781   -2.0240   -0.2377 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4013   -0.7832    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6614   -0.2280    0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7811    1.1245    0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6846    1.9320    0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4200    1.3829    0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3084    0.0302    0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479    1.0184   -2.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9706    0.2736    1.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2144    1.8707    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7454   -2.1605   -0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9349   -2.1667   -0.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    0.7073    0.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9729   -2.8677   -0.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6263   -2.8404   -0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5394   -0.8390   -0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8016    1.5212    0.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7806    2.9790    0.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209    1.9503    0.6654 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  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 10  1  0
 18 13  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

  Mrv1652307171819202D          

 20 21  0  0  0  0            999 V2000
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -0.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400   -1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0470   -2.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9851   -1.0568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -1.4984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3020   -2.7976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5990   -1.3998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752    0.5124    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  2  0  0  0  0
  9  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  3  2  0  0  0  0
 10  9  1  0  0  0  0
 11  4  2  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  1  0  0  0  0
 15  8  1  4  0  0  0
 15 12  2  0  0  0  0
 16 12  1  0  0  0  0
 17 13  2  0  0  0  0
 18 13  1  0  0  0  0
 19  5  1  0  0  0  0
 20  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0006005

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(=C(\[H])C1=CNC2=CC=CC=C12)C(O)=NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H12N2O3/c16-12(15-8-13(17)18)6-5-9-7-14-11-4-2-1-3-10(9)11/h1-7,14H,8H2,(H,15,16)(H,17,18)/b6-5+

> <INCHI_KEY>
DUIFVCFSAWHIOD-AATRIKPKSA-N

> <FORMULA>
C13H12N2O3

> <MOLECULAR_WEIGHT>
244.246

> <EXACT_MASS>
244.08479226

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
25.57760927771007

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{[(2E)-1-hydroxy-3-(1H-indol-3-yl)prop-2-en-1-ylidene]amino}acetic acid

> <ALOGPS_LOGP>
1.75

> <JCHEM_LOGP>
1.798192722615574

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.310983814141601

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.028170647673737

> <JCHEM_PKA_STRONGEST_BASIC>
2.368192071160439

> <JCHEM_POLAR_SURFACE_AREA>
85.67999999999999

> <JCHEM_REFRACTIVITY>
67.4716

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[(2E)-1-hydroxy-3-(1H-indol-3-yl)prop-2-en-1-ylidene]amino}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006005
     RDKit          3D
Indolylacryloylglycine
 30 31  0  0  0  0  0  0  0  0999 V2000
    5.9702    1.8248   -0.8946 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7944    1.3457   -0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0092    1.1882   -1.9094 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2704    0.9603    0.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9455    0.4563    0.4197 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -0.7322    0.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5817   -1.6897   -0.0413 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2172   -1.1420    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2017   -0.3072    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1907   -0.7508    0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6361   -2.0340   -0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781   -2.0240   -0.2377 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4013   -0.7832    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6614   -0.2280    0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7811    1.1245    0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6846    1.9320    0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4200    1.3829    0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3084    0.0302    0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479    1.0184   -2.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9706    0.2736    1.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2144    1.8707    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7454   -2.1605   -0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9349   -2.1667   -0.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    0.7073    0.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9729   -2.8677   -0.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6263   -2.8404   -0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5394   -0.8390   -0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8016    1.5212    0.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7806    2.9790    0.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209    1.9503    0.6654 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  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 10  1  0
 18 13  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

HEADER    PROTEIN                                 17-JUL-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUL-18         0                                  
HETATM    1  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.143  -0.188   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.315  -3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.333  -1.652   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.821  -3.757   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      -1.839  -1.973   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       0.698  -2.797   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.297  -5.222   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -4.852  -2.613   0.000  0.00  0.00           O+0
HETATM   19  H   UNK     0       2.680  -1.012   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0      -0.887   0.957   0.000  0.00  0.00           H+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   10                                                       
CONECT    4    2   11                                                       
CONECT    5    6    9   19                                                  
CONECT    6    5   12   20                                                  
CONECT    7    9   14                                                       
CONECT    8   13   15                                                       
CONECT    9    5    7   10                                                  
CONECT   10    3    9   11                                                  
CONECT   11    4   10   14                                                  
CONECT   12    6   15   16                                                  
CONECT   13    8   17   18                                                  
CONECT   14    7   11                                                       
CONECT   15    8   12                                                       
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18   13                                                            
CONECT   19    5                                                            
CONECT   20    6                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0006005
HETATM    1  O1  UNL     1       5.970   1.825  -0.895  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.794   1.346  -0.777  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.009   1.188  -1.909  1.00  0.00           O  
HETATM    4  C2  UNL     1       4.270   0.960   0.556  1.00  0.00           C  
HETATM    5  N1  UNL     1       2.946   0.456   0.420  1.00  0.00           N  
HETATM    6  C3  UNL     1       2.606  -0.732   0.151  1.00  0.00           C  
HETATM    7  O3  UNL     1       3.582  -1.690  -0.041  1.00  0.00           O  
HETATM    8  C4  UNL     1       1.217  -1.142   0.035  1.00  0.00           C  
HETATM    9  C5  UNL     1       0.202  -0.307   0.200  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.191  -0.751   0.076  1.00  0.00           C  
HETATM   11  C7  UNL     1      -1.636  -2.034  -0.215  1.00  0.00           C  
HETATM   12  N2  UNL     1      -2.978  -2.024  -0.238  1.00  0.00           N  
HETATM   13  C8  UNL     1      -3.401  -0.783   0.028  1.00  0.00           C  
HETATM   14  C9  UNL     1      -4.661  -0.228   0.127  1.00  0.00           C  
HETATM   15  C10 UNL     1      -4.781   1.124   0.422  1.00  0.00           C  
HETATM   16  C11 UNL     1      -3.685   1.932   0.621  1.00  0.00           C  
HETATM   17  C12 UNL     1      -2.420   1.383   0.524  1.00  0.00           C  
HETATM   18  C13 UNL     1      -2.308   0.030   0.228  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.448   1.018  -2.809  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.971   0.274   1.084  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.214   1.871   1.221  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.745  -2.160  -0.920  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.935  -2.167  -0.196  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.394   0.707   0.427  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.973  -2.868  -0.386  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.626  -2.840  -0.430  1.00  0.00           H  
HETATM   27  H9  UNL     1      -5.539  -0.839  -0.024  1.00  0.00           H  
HETATM   28  H10 UNL     1      -5.802   1.521   0.491  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.781   2.979   0.850  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.521   1.950   0.665  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   19
CONECT    4    5   20   21
CONECT    5    6    6
CONECT    6    7    8
CONECT    7   22
CONECT    8    9    9   23
CONECT    9   10   24
CONECT   10   11   11   18
CONECT   11   12   25
CONECT   12   13   26
CONECT   13   14   14   18
CONECT   14   15   27
CONECT   15   16   16   28
CONECT   16   17   29
CONECT   17   18   18   30
END

HMDB0006005
     RDKit          3D
Indolylacryloylglycine
 30 31  0  0  0  0  0  0  0  0999 V2000
    5.9702    1.8248   -0.8946 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7944    1.3457   -0.7770 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0092    1.1882   -1.9094 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2704    0.9603    0.5556 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9455    0.4563    0.4197 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056   -0.7322    0.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5817   -1.6897   -0.0413 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2172   -1.1420    0.0352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2017   -0.3072    0.2001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1907   -0.7508    0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6361   -2.0340   -0.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781   -2.0240   -0.2377 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4013   -0.7832    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6614   -0.2280    0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7811    1.1245    0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6846    1.9320    0.6209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4200    1.3829    0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3084    0.0302    0.2275 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479    1.0184   -2.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9706    0.2736    1.0839 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2144    1.8707    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7454   -2.1605   -0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9349   -2.1667   -0.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    0.7073    0.4273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9729   -2.8677   -0.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6263   -2.8404   -0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5394   -0.8390   -0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8016    1.5212    0.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7806    2.9790    0.8498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5209    1.9503    0.6654 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  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 10  1  0
 18 13  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 11 25  1  0
 12 26  1  0
 14 27  1  0
 15 28  1  0
 16 29  1  0
 17 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
IAG	HMDB
Indole-3-acryloyl-glycine	HMDB
Indoleacrylic glycine	HMDB
Indolyl acryloylglycine	HMDB
N-(3-(1-indol-3-yl)-1-oxo-2-Propenyl)glycine	HMDB
Indolylacryloylglycine, (e)-isomer	MeSH, HMDB
Indolyl-3-acryloylglycine	MeSH, HMDB
2-{[(2E)-1-hydroxy-3-(1H-indol-3-yl)prop-2-en-1-ylidene]amino}acetate	Generator, HMDB
Indolylacryloylglycine	MeSH

Chemical Formula

C₁₃H₁₂N₂O₃

Average Molecular Weight

244.246

Monoisotopic Molecular Weight

244.08479226

IUPAC Name

2-{[(2E)-1-hydroxy-3-(1H-indol-3-yl)prop-2-en-1-ylidene]amino}acetic acid

Traditional Name

{[(2E)-1-hydroxy-3-(1H-indol-3-yl)prop-2-en-1-ylidene]amino}acetic acid

CAS Registry Number

3475-68-1

SMILES

[H]\C(=C(\[H])C1=CNC2=CC=CC=C12)C(O)=NCC(O)=O

InChI Identifier

InChI=1S/C13H12N2O3/c16-12(15-8-13(17)18)6-5-9-7-14-11-4-2-1-3-10(9)11/h1-7,14H,8H2,(H,15,16)(H,17,18)/b6-5+

InChI Key

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0006005)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.076 g/L	ALOGPS
logP	1.75	ALOGPS
logP	1.8	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.03	ChemAxon
pKa (Strongest Basic)	2.37	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	85.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	67.47 m³·mol⁻¹	ChemAxon
Polarizability	25.58 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-2H]-	186.859	30932474
DeepCCS	[M+Na]+	162.283	30932474
AllCCS	[M+H]+	154.6	32859911
AllCCS	[M+H-H2O]+	150.8	32859911
AllCCS	[M+NH4]+	158.1	32859911
AllCCS	[M+Na]+	159.1	32859911
AllCCS	[M-H]-	157.3	32859911
AllCCS	[M+Na-2H]-	157.1	32859911
AllCCS	[M+HCOO]-	157.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Indolylacryloylglycine	[H]\C(=C(\[H])C1=CNC2=CC=CC=C12)C(O)=NCC(O)=O	3872.4	Standard polar	33892256
Indolylacryloylglycine	[H]\C(=C(\[H])C1=CNC2=CC=CC=C12)C(O)=NCC(O)=O	2400.7	Standard non polar	33892256
Indolylacryloylglycine	[H]\C(=C(\[H])C1=CNC2=CC=CC=C12)C(O)=NCC(O)=O	2569.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Indolylacryloylglycine,1TMS,isomer #1	C[Si](C)(C)OC(/C=C/C1=C[NH]C2=CC=CC=C12)=NCC(=O)O	2746.8	Semi standard non polar	33892256
Indolylacryloylglycine,1TMS,isomer #2	C[Si](C)(C)OC(=O)CN=C(O)/C=C/C1=C[NH]C2=CC=CC=C12	2717.7	Semi standard non polar	33892256
Indolylacryloylglycine,1TMS,isomer #3	C[Si](C)(C)N1C=C(/C=C/C(O)=NCC(=O)O)C2=CC=CC=C21	2864.9	Semi standard non polar	33892256
Indolylacryloylglycine,2TMS,isomer #1	C[Si](C)(C)OC(=O)CN=C(/C=C/C1=C[NH]C2=CC=CC=C12)O[Si](C)(C)C	2718.9	Semi standard non polar	33892256
Indolylacryloylglycine,2TMS,isomer #2	C[Si](C)(C)OC(/C=C/C1=CN([Si](C)(C)C)C2=CC=CC=C12)=NCC(=O)O	2845.2	Semi standard non polar	33892256
Indolylacryloylglycine,2TMS,isomer #3	C[Si](C)(C)OC(=O)CN=C(O)/C=C/C1=CN([Si](C)(C)C)C2=CC=CC=C12	2812.4	Semi standard non polar	33892256
Indolylacryloylglycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN=C(/C=C/C1=CN([Si](C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C	2786.2	Semi standard non polar	33892256
Indolylacryloylglycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN=C(/C=C/C1=CN([Si](C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C	2591.7	Standard non polar	33892256
Indolylacryloylglycine,3TMS,isomer #1	C[Si](C)(C)OC(=O)CN=C(/C=C/C1=CN([Si](C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C	2956.5	Standard polar	33892256
Indolylacryloylglycine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(/C=C/C1=C[NH]C2=CC=CC=C12)=NCC(=O)O	3007.9	Semi standard non polar	33892256
Indolylacryloylglycine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CN=C(O)/C=C/C1=C[NH]C2=CC=CC=C12	2992.6	Semi standard non polar	33892256
Indolylacryloylglycine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=C(/C=C/C(O)=NCC(=O)O)C2=CC=CC=C21	3079.6	Semi standard non polar	33892256
Indolylacryloylglycine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN=C(/C=C/C1=C[NH]C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C	3216.9	Semi standard non polar	33892256
Indolylacryloylglycine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(/C=C/C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)=NCC(=O)O	3274.4	Semi standard non polar	33892256
Indolylacryloylglycine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)CN=C(O)/C=C/C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	3252.4	Semi standard non polar	33892256
Indolylacryloylglycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN=C(/C=C/C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C	3395.8	Semi standard non polar	33892256
Indolylacryloylglycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN=C(/C=C/C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C	3171.8	Standard non polar	33892256
Indolylacryloylglycine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CN=C(/C=C/C1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)O[Si](C)(C)C(C)(C)C	3154.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Indolylacryloylglycine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-1910000000-af9421f979b84f7c1d21	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indolylacryloylglycine GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-5920000000-34a6af95e2fa1e07e867	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indolylacryloylglycine 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 - Indolylacryloylglycine 10V, Positive-QTOF	splash10-002b-4590000000-bfd50d5180c6bd14c6cd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indolylacryloylglycine 20V, Positive-QTOF	splash10-056r-9710000000-8b4ac64ee5199a960b5e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indolylacryloylglycine 40V, Positive-QTOF	splash10-056u-7900000000-12988d991d4fb8d3f60c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indolylacryloylglycine 10V, Negative-QTOF	splash10-0006-0190000000-4a969f2be20f7b81f7fb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indolylacryloylglycine 20V, Negative-QTOF	splash10-006x-6890000000-d7bb4b025f6e9caddfc7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indolylacryloylglycine 40V, Negative-QTOF	splash10-05fu-9400000000-0ac0d883ab78f58631e6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indolylacryloylglycine 10V, Negative-QTOF	splash10-006x-0960000000-27152d1fd1bb75d52117	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indolylacryloylglycine 20V, Negative-QTOF	splash10-006x-2920000000-95b20ae472699500646a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indolylacryloylglycine 40V, Negative-QTOF	splash10-0006-0900000000-e1ada5cb92852f044560	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indolylacryloylglycine 10V, Positive-QTOF	splash10-002b-0190000000-d2eeedccf34de3bbcbb5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indolylacryloylglycine 20V, Positive-QTOF	splash10-006x-0910000000-19365eb3817e6e25ff6f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indolylacryloylglycine 40V, Positive-QTOF	splash10-0006-0900000000-e7f97c6d0f9554f2ee7a	2021-09-22	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

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	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

FDB023799

KNApSAcK ID

Not Available

Chemspider ID

4521424

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5370648

PDB ID

Not Available

ChEBI ID

145761

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

Bull G, Shattock P, Whiteley P, Anderson R, Groundwater PW, Lough JW, Lees G: Indolyl-3-acryloylglycine (IAG) is a putative diagnostic urinary marker for autism spectrum disorders. Med Sci Monit. 2003 Oct;9(10):CR422-5. [PubMed:14523330 ]
Wright B, Brzozowski AM, Calvert E, Farnworth H, Goodall DM, Holbrook I, Imrie G, Jordan J, Kelly A, Miles J, Smith R, Town J: Is the presence of urinary indolyl-3-acryloylglycine associated with autism spectrum disorder? Dev Med Child Neurol. 2005 Mar;47(3):190-2. [PubMed:15739724 ]
Anderson RJ, Bendell DJ, Garnett I, Groundwater PW, Lough WJ, Mills MJ, Savery D, Shattock PE: Identification of indolyl-3-acryloylglycine in the urine of people with autism. J Pharm Pharmacol. 2002 Feb;54(2):295-8. [PubMed:11858215 ]
Marklova E: Where does indolylacrylic acid come from? Amino Acids. 1999;17(4):401-13. [PubMed:10707769 ]
Wlodarska M, Luo C, Kolde R, d'Hennezel E, Annand JW, Heim CE, Krastel P, Schmitt EK, Omar AS, Creasey EA, Garner AL, Mohammadi S, O'Connell DJ, Abubucker S, Arthur TD, Franzosa EA, Huttenhower C, Murphy LO, Haiser HJ, Vlamakis H, Porter JA, Xavier RJ: Indoleacrylic Acid Produced by Commensal Peptostreptococcus Species Suppresses Inflammation. Cell Host Microbe. 2017 Jul 12;22(1):25-37.e6. doi: 10.1016/j.chom.2017.06.007. [PubMed:28704649 ]
Kumavath RN, Ramana ChV, Sasikala Ch, Barh D, Kumar AP, Azevedo V: Isolation and Characterization of L-Tryptophan Ammonia Lyase from Rubrivivax benzoatilyticus Strain JA2. Curr Protein Pept Sci. 2015;16(8):775-81. doi: 10.2174/1389203716666150505235929. [PubMed:25961404 ]
Wang L, Angley MT, Gerber JP, Young RL, Abarno DV, McKinnon RA, Sorich MJ: Is urinary indolyl-3-acryloylglycine a biomarker for autism with gastrointestinal symptoms? Biomarkers. 2009 Dec;14(8):596-603. doi: 10.3109/13547500903183962. [PubMed:19697973 ]
Dalton NR, Chandler S, Turner C, Charman T, Pickles A, Simonoff E, Baird G: Measurement of urine indolylacroylglycine is not useful in the diagnosis or dietary management of autism. Autism Res. 2017 Mar;10(3):408-413. doi: 10.1002/aur.1688. Epub 2016 Aug 29. [PubMed:27569540 ]
Wilson J, Wright B, Jost S, Smith R, Pearce H, Richardson S: Can urinary indolylacroylglycine levels be used to determine whether children with autism will benefit from dietary intervention? Pediatr Res. 2017 Apr;81(4):672-679. doi: 10.1038/pr.2016.256. Epub 2016 Nov 23. [PubMed:27879968 ]
Liu X, Cheng X, Liu X, He L, Zhang W, Wang Y, Sun W, Ji Z: Investigation of the urinary metabolic variations and the application in bladder cancer biomarker discovery. Int J Cancer. 2018 Jul 15;143(2):408-418. doi: 10.1002/ijc.31323. Epub 2018 Mar 2. [PubMed:29451296 ]

Showing metabocard for Indolylacryloylglycine (HMDB0006005)

MOL for HMDB0006005 (Indolylacryloylglycine)

3D MOL for HMDB0006005 (Indolylacryloylglycine)

3D SDF for HMDB0006005 (Indolylacryloylglycine)

3D-SDF for HMDB0006005 (Indolylacryloylglycine)

PDB for HMDB0006005 (Indolylacryloylglycine)

3D PDB for HMDB0006005 (Indolylacryloylglycine)

SMILES for HMDB0006005 (Indolylacryloylglycine)

INCHI for HMDB0006005 (Indolylacryloylglycine)

Structure for HMDB0006005 (Indolylacryloylglycine)

3D Structure for HMDB0006005 (Indolylacryloylglycine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra