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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:17:26 UTC

Update Date

2022-03-07 02:56:00 UTC

HMDB ID

HMDB0038942

Secondary Accession Numbers

HMDB38942

Metabolite Identification

Common Name

Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid

Description

Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid, also known as methyl 2-(2,3,5-trihydroxy-3H-indol-3-yl)acetic acid, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid has been detected, but not quantified in, breakfast cereal and cereals and cereal products. This could make methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid.

Structure

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

HMDB0038942
     RDKit          3D
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid
 28 29  0  0  0  0  0  0  0  0999 V2000
    4.5164    0.4138    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1218    0.3143    0.4324 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4514    0.7938   -0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1894    1.3519   -1.5496 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9983    0.7206   -0.9034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960   -0.0421    0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5407    0.6147    1.4123 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6537   -1.4591    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361   -1.9506    0.3658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5350   -2.2072    0.1020 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6235   -1.3034   -0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9991   -1.5579   -0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9145   -0.5362   -0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4501    0.7628   -0.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3827    1.7794   -0.3359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1068    1.0044   -0.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708   -0.0187    0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0912    0.4378   -0.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7699    1.2894    1.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8449   -0.4823    1.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6112    1.7595   -0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8320    0.1911   -1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758   -0.0037    1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5787   -3.2631    0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3213   -2.5886   -0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9798   -0.7649   -0.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0435    2.7327   -0.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7230    2.0116   -0.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17  6  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
 15 27  1  0
 16 28  1  0
M  END

  Mrv0541 02241208502D          

 17 18  0  0  0  0            999 V2000
   -2.1832   -1.0916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3742   -1.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083   -0.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9701    0.0410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6978    0.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3450   -0.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2124   -2.1429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0805    1.3339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4049    0.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2423    0.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9701    0.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3750    1.0916    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5367   -0.2826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3450   -0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083    2.1429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9701    1.3339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6978    1.0916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5 17  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 16  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038942

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)CC1(O)C(=O)NC2=C1C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C11H11NO5/c1-17-9(14)5-11(16)7-4-6(13)2-3-8(7)12-10(11)15/h2-4,13,16H,5H2,1H3,(H,12,15)

> <INCHI_KEY>
YPPHXVJCTQPTBV-UHFFFAOYSA-N

> <FORMULA>
C11H11NO5

> <MOLECULAR_WEIGHT>
237.2087

> <EXACT_MASS>
237.063722467

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
22.516485165067117

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-(3,5-dihydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate

> <ALOGPS_LOGP>
0.54

> <JCHEM_LOGP>
-0.009825563333333596

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.702955225107095

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.253427448684828

> <JCHEM_PKA_STRONGEST_BASIC>
-4.293344908590368

> <JCHEM_POLAR_SURFACE_AREA>
95.86000000000001

> <JCHEM_REFRACTIVITY>
58.421800000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.10e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-(3,5-dihydroxy-2-oxo-1H-indol-3-yl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038942
     RDKit          3D
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid
 28 29  0  0  0  0  0  0  0  0999 V2000
    4.5164    0.4138    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1218    0.3143    0.4324 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4514    0.7938   -0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1894    1.3519   -1.5496 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9983    0.7206   -0.9034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960   -0.0421    0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5407    0.6147    1.4123 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6537   -1.4591    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361   -1.9506    0.3658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5350   -2.2072    0.1020 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6235   -1.3034   -0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9991   -1.5579   -0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9145   -0.5362   -0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4501    0.7628   -0.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3827    1.7794   -0.3359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1068    1.0044   -0.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708   -0.0187    0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0912    0.4378   -0.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7699    1.2894    1.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8449   -0.4823    1.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6112    1.7595   -0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8320    0.1911   -1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758   -0.0037    1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5787   -3.2631    0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3213   -2.5886   -0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9798   -0.7649   -0.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0435    2.7327   -0.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7230    2.0116   -0.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17  6  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
 15 27  1  0
 16 28  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.075  -2.038   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.565  -2.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.509  -1.434   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.811   0.077   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.169   0.528   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.377  -0.528   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.263  -4.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.150   2.490   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.756   1.282   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.452   0.377   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.811   0.679   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.567   2.038   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.869  -0.528   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.377  -0.225   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.509   4.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.811   2.490   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -3.169   2.038   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6   17                                                  
CONECT    6    1    5                                                       
CONECT    7    2                                                            
CONECT    8    9                                                            
CONECT    9    4    8   10   16                                             
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   16                                                            
CONECT   16    9   15   17                                                  
CONECT   17    5   16                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0038942
HETATM    1  C1  UNL     1       4.516   0.414   0.605  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.122   0.314   0.432  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.451   0.794  -0.667  1.00  0.00           C  
HETATM    4  O2  UNL     1       3.189   1.352  -1.550  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.998   0.721  -0.903  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.296  -0.042   0.193  1.00  0.00           C  
HETATM    7  O3  UNL     1       0.541   0.615   1.412  1.00  0.00           O  
HETATM    8  C5  UNL     1       0.654  -1.459   0.234  1.00  0.00           C  
HETATM    9  O4  UNL     1       1.836  -1.951   0.366  1.00  0.00           O  
HETATM   10  N1  UNL     1      -0.535  -2.207   0.102  1.00  0.00           N  
HETATM   11  C6  UNL     1      -1.623  -1.303  -0.021  1.00  0.00           C  
HETATM   12  C7  UNL     1      -2.999  -1.558  -0.175  1.00  0.00           C  
HETATM   13  C8  UNL     1      -3.915  -0.536  -0.280  1.00  0.00           C  
HETATM   14  C9  UNL     1      -3.450   0.763  -0.230  1.00  0.00           C  
HETATM   15  O5  UNL     1      -4.383   1.779  -0.336  1.00  0.00           O  
HETATM   16  C10 UNL     1      -2.107   1.004  -0.079  1.00  0.00           C  
HETATM   17  C11 UNL     1      -1.171  -0.019   0.027  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.091   0.438  -0.317  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.770   1.289   1.260  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.845  -0.482   1.202  1.00  0.00           H  
HETATM   21  H4  UNL     1       0.611   1.759  -0.915  1.00  0.00           H  
HETATM   22  H5  UNL     1       0.832   0.191  -1.861  1.00  0.00           H  
HETATM   23  H6  UNL     1       1.076  -0.004   1.958  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.579  -3.263   0.099  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.321  -2.589  -0.209  1.00  0.00           H  
HETATM   26  H9  UNL     1      -4.980  -0.765  -0.399  1.00  0.00           H  
HETATM   27  H10 UNL     1      -4.044   2.733  -0.299  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.723   2.012  -0.038  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   21   22
CONECT    6    7    8   17
CONECT    7   23
CONECT    8    9    9   10
CONECT   10   11   24
CONECT   11   12   12   17
CONECT   12   13   25
CONECT   13   14   14   26
CONECT   14   15   16
CONECT   15   27
CONECT   16   17   17   28
END

HMDB0038942
     RDKit          3D
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid
 28 29  0  0  0  0  0  0  0  0999 V2000
    4.5164    0.4138    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1218    0.3143    0.4324 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4514    0.7938   -0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1894    1.3519   -1.5496 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9983    0.7206   -0.9034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2960   -0.0421    0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5407    0.6147    1.4123 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6537   -1.4591    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361   -1.9506    0.3658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5350   -2.2072    0.1020 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6235   -1.3034   -0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9991   -1.5579   -0.1751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9145   -0.5362   -0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4501    0.7628   -0.2297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3827    1.7794   -0.3359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1068    1.0044   -0.0794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1708   -0.0187    0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0912    0.4378   -0.3167 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7699    1.2894    1.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8449   -0.4823    1.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6112    1.7595   -0.9146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8320    0.1911   -1.8607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758   -0.0037    1.9582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5787   -3.2631    0.0989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3213   -2.5886   -0.2093 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9798   -0.7649   -0.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0435    2.7327   -0.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7230    2.0116   -0.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17  6  1  0
 17 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
 15 27  1  0
 16 28  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetate	Generator
Methyl 2-(2,3,5-trihydroxy-3H-indol-3-yl)acetic acid	HMDB

Chemical Formula

C₁₁H₁₁NO₅

Average Molecular Weight

237.2087

Monoisotopic Molecular Weight

237.063722467

IUPAC Name

methyl 2-(3,5-dihydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate

Traditional Name

methyl 2-(3,5-dihydroxy-2-oxo-1H-indol-3-yl)acetate

CAS Registry Number

57061-18-4

SMILES

COC(=O)CC1(O)C(=O)NC2=C1C=C(O)C=C2

InChI Identifier

InChI=1S/C11H11NO5/c1-17-9(14)5-11(16)7-4-6(13)2-3-8(7)12-10(11)15/h2-4,13,16H,5H2,1H3,(H,12,15)

InChI Key

YPPHXVJCTQPTBV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
Indole
Dihydroindole
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Methyl ester
Tertiary alcohol
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Lactam
Carboxylic acid derivative
Azacycle
Monocarboxylic acid or derivatives
Alcohol
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038942)
Cytoplasm (HMDB: HMDB0038942)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038942)

Source

Exogenous

Exogenous (HMDB: HMDB0038942)

Food

Food (HMDB: HMDB0038942)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Endogenous

Plant

Poaceae (HMDB: HMDB0038942)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038942)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	78 - 80 °C	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	8.1 g/L	ALOGPS
logP	0.54	ALOGPS
logP	-0.0098	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	9.25	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.86 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	58.42 m³·mol⁻¹	ChemAxon
Polarizability	22.52 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
DarkChem	[M+H]+	156.828	31661259
DarkChem	[M-H]-	152.836	31661259
DeepCCS	[M+H]+	157.196	30932474
DeepCCS	[M-H]-	154.838	30932474
DeepCCS	[M-2H]-	187.764	30932474
DeepCCS	[M+Na]+	163.289	30932474
AllCCS	[M+H]+	151.7	32859911
AllCCS	[M+H-H2O]+	147.8	32859911
AllCCS	[M+NH4]+	155.3	32859911
AllCCS	[M+Na]+	156.4	32859911
AllCCS	[M-H]-	151.7	32859911
AllCCS	[M+Na-2H]-	151.7	32859911
AllCCS	[M+HCOO]-	151.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid	COC(=O)CC1(O)C(=O)NC2=C1C=C(O)C=C2	3729.3	Standard polar	33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid	COC(=O)CC1(O)C(=O)NC2=C1C=C(O)C=C2	1883.1	Standard non polar	33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid	COC(=O)CC1(O)C(=O)NC2=C1C=C(O)C=C2	2359.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,1TMS,isomer #1	COC(=O)CC1(O[Si](C)(C)C)C(=O)NC2=CC=C(O)C=C21	2149.3	Semi standard non polar	33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,1TMS,isomer #2	COC(=O)CC1(O)C(=O)NC2=CC=C(O[Si](C)(C)C)C=C21	2177.5	Semi standard non polar	33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,1TMS,isomer #3	COC(=O)CC1(O)C(=O)N([Si](C)(C)C)C2=CC=C(O)C=C21	2085.3	Semi standard non polar	33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,2TMS,isomer #1	COC(=O)CC1(O[Si](C)(C)C)C(=O)NC2=CC=C(O[Si](C)(C)C)C=C21	2245.7	Semi standard non polar	33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,2TMS,isomer #2	COC(=O)CC1(O[Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=CC=C(O)C=C21	2070.7	Semi standard non polar	33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,2TMS,isomer #3	COC(=O)CC1(O)C(=O)N([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C21	2152.1	Semi standard non polar	33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,3TMS,isomer #1	COC(=O)CC1(O[Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C21	2203.2	Semi standard non polar	33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,3TMS,isomer #1	COC(=O)CC1(O[Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C21	2184.6	Standard non polar	33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,1TBDMS,isomer #1	COC(=O)CC1(O[Si](C)(C)C(C)(C)C)C(=O)NC2=CC=C(O)C=C21	2381.1	Semi standard non polar	33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,1TBDMS,isomer #2	COC(=O)CC1(O)C(=O)NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C21	2425.7	Semi standard non polar	33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,1TBDMS,isomer #3	COC(=O)CC1(O)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C21	2348.5	Semi standard non polar	33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,2TBDMS,isomer #1	COC(=O)CC1(O[Si](C)(C)C(C)(C)C)C(=O)NC2=CC=C(O[Si](C)(C)C(C)(C)C)C=C21	2670.5	Semi standard non polar	33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,2TBDMS,isomer #2	COC(=O)CC1(O[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C21	2570.8	Semi standard non polar	33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,2TBDMS,isomer #3	COC(=O)CC1(O)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C21	2640.2	Semi standard non polar	33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,3TBDMS,isomer #1	COC(=O)CC1(O[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C21	2848.6	Semi standard non polar	33892256
Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid,3TBDMS,isomer #1	COC(=O)CC1(O[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C21	2816.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-08fr-1920000000-341a149da27672ffa231	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-3119000000-dc21343dcf4903151141	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 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 - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 10V, Positive-QTOF	splash10-052r-0290000000-70f8a8822eee1d2eb1f7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 20V, Positive-QTOF	splash10-03di-0920000000-5d5f8a1f1635a91fdbdc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 40V, Positive-QTOF	splash10-06to-5900000000-a72d8e05f5bbf07d8a89	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 10V, Negative-QTOF	splash10-000i-1390000000-53331e4005631dc2f52f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 20V, Negative-QTOF	splash10-03di-3950000000-2c7f1ebda7a3d553c961	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 40V, Negative-QTOF	splash10-001l-5900000000-295fa2abc6f3b1fe4e56	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 10V, Positive-QTOF	splash10-000i-0190000000-dbb0178dbb630b1c4d64	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 20V, Positive-QTOF	splash10-052r-0690000000-b9ec47421043a6137895	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 40V, Positive-QTOF	splash10-0a4i-7900000000-ac0322a62f5ca31abb07	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 10V, Negative-QTOF	splash10-0udi-0190000000-9de2f90d912bddc140af	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 20V, Negative-QTOF	splash10-01t9-0910000000-d077b917e584095e909f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid 40V, Negative-QTOF	splash10-0006-9400000000-d29b858e645a8ddbc7c6	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB018418

KNApSAcK ID

Not Available

Chemspider ID

22943185

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45782784

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid (HMDB0038942)

MOL for HMDB0038942 (Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid)

3D MOL for HMDB0038942 (Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid)

3D SDF for HMDB0038942 (Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid)

3D-SDF for HMDB0038942 (Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid)

PDB for HMDB0038942 (Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid)

3D PDB for HMDB0038942 (Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid)

SMILES for HMDB0038942 (Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid)

INCHI for HMDB0038942 (Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid)

Structure for HMDB0038942 (Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid)

3D Structure for HMDB0038942 (Methyl 2,3-dihydro-3,5-dihydroxy-2-oxo-3-indoleacetic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra