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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2009-11-30 15:50:40 UTC

Update Date

2021-09-14 15:39:02 UTC

HMDB ID

HMDB0013189

Secondary Accession Numbers

HMDB13189

Metabolite Identification

Common Name

3-Indole carboxylic acid glucuronide

Description

3-Indole carboxylic acid glucuronide is a natural human metabolites of Indole-3-carboxylic acid. Indole-3-carboxylic acid is a normal urinary indolic tryptophan metabolite (PMID 4844607 ) and has been found elevated in patients with liver diseases (PMID 13905029 ). Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys.

Structure

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

HMDB0013189
     RDKit          3D
3-Indole carboxylic acid glucuronide
 39 41  0  0  0  0  0  0  0  0999 V2000
    1.3485   -1.7358   -0.2872 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0696   -0.5173   -0.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2614   -0.1485   -0.0571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2943   -1.0914   -0.0797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1376   -0.9137   -1.1731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7962    0.2906   -1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9201    0.2541   -2.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1454   -0.7774   -2.8039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7450    1.3500   -2.3107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4227    0.5823    0.2060 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6700    1.1749    0.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4985   -0.7629    0.9028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3069   -0.7233    2.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0654   -1.1270    1.2325 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9601   -2.3417    1.8772 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1508    0.4485   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0564    1.8359   -0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2719    2.3727   -0.0409 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1863    1.3803   -0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5599    1.4045   -0.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2678    0.2399   -0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6207   -0.9742   -0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2457   -0.9759   -0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    0.1880   -0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423   -2.0982   -0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501    1.1519   -1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7482    1.2663   -2.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7433    1.2694    0.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2356    0.7953    0.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8549   -1.5376    0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6354   -1.6615    2.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6552   -0.3026    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1279   -2.7998    1.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027    2.3452    0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5205    3.3824    0.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0924    2.3380   -0.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3619    0.2359   -0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1636   -1.9050   -0.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6986   -1.9125   -0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 14  4  1  0
 24 16  1  0
 24 19  1  0
  4 25  1  6
  6 26  1  0
  9 27  1  0
 10 28  1  1
 11 29  1  0
 12 30  1  6
 13 31  1  0
 14 32  1  1
 15 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 23 39  1  0
M  END


  Mrv1652303102016502D          

 24 26  0  0  1  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    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
    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
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    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
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768    3.1465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    3.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809    4.3727    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3739    4.5442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1190    5.3289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6710    5.9420    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4780    5.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329    4.9858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0300    6.3835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751    7.1682    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8370    6.2120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161    6.7266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6880    5.5004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    3.9312    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  4  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  1  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 16 22  1  6  0  0  0
 15 23  1  1  0  0  0
 14 24  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0013189

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@@H]1[C@@H](O)[C@H](OC(=O)C2=CNC3=CC=CC=C23)OC([C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H15NO8/c17-9-10(18)12(13(20)21)23-15(11(9)19)24-14(22)7-5-16-8-4-2-1-3-6(7)8/h1-5,9-12,15-19H,(H,20,21)/t9-,10-,11+,12?,15-/m0/s1

> <INCHI_KEY>
BDNWJTRKUBXAGH-DOVARBIBSA-N

> <FORMULA>
C15H15NO8

> <MOLECULAR_WEIGHT>
337.2815

> <EXACT_MASS>
337.079766461

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
32.03828364333073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4S,5R,6S)-3,4,5-trihydroxy-6-(1H-indole-3-carbonyloxy)oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
-0.018202838333332964

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.856966534314665

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.2930996338716634

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6869065425044596

> <JCHEM_POLAR_SURFACE_AREA>
149.31

> <JCHEM_REFRACTIVITY>
76.6993

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,5R,6S)-3,4,5-trihydroxy-6-(1H-indole-3-carbonyloxy)oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013189
     RDKit          3D
3-Indole carboxylic acid glucuronide
 39 41  0  0  0  0  0  0  0  0999 V2000
    1.3485   -1.7358   -0.2872 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0696   -0.5173   -0.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2614   -0.1485   -0.0571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2943   -1.0914   -0.0797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1376   -0.9137   -1.1731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7962    0.2906   -1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9201    0.2541   -2.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1454   -0.7774   -2.8039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7450    1.3500   -2.3107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4227    0.5823    0.2060 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6700    1.1749    0.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4985   -0.7629    0.9028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3069   -0.7233    2.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0654   -1.1270    1.2325 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9601   -2.3417    1.8772 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1508    0.4485   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0564    1.8359   -0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2719    2.3727   -0.0409 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1863    1.3803   -0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5599    1.4045   -0.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2678    0.2399   -0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6207   -0.9742   -0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2457   -0.9759   -0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    0.1880   -0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423   -2.0982   -0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501    1.1519   -1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7482    1.2663   -2.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7433    1.2694    0.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2356    0.7953    0.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8549   -1.5376    0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6354   -1.6615    2.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6552   -0.3026    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1279   -2.7998    1.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027    2.3452    0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5205    3.3824    0.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0924    2.3380   -0.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3619    0.2359   -0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1636   -1.9050   -0.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6986   -1.9125   -0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 14  4  1  0
 24 16  1  0
 24 19  1  0
  4 25  1  6
  6 26  1  0
  9 27  1  0
 10 28  1  1
 11 29  1  0
 12 30  1  6
 13 31  1  0
 14 32  1  1
 15 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 23 39  1  0
M  END

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   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       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       1.650   5.553   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.143   5.873   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.680   6.698   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.204   8.162   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.698   8.483   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.222   9.947   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.253  11.092   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.759  10.771   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.235   9.307   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.789  11.916   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.314  13.381   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.296  11.596   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.777  12.556   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -1.284  10.267   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.332   7.338   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   18                                                  
CONECT   14   13   15   24                                                  
CONECT   15   14   16   23                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16                                                            
CONECT   23   15                                                            
CONECT   24   14                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0013189
HETATM    1  O1  UNL     1       1.349  -1.736  -0.287  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.070  -0.517  -0.165  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.261  -0.149  -0.057  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.294  -1.091  -0.080  1.00  0.00           C  
HETATM    5  O3  UNL     1      -2.138  -0.914  -1.173  1.00  0.00           O  
HETATM    6  C3  UNL     1      -2.796   0.291  -1.163  1.00  0.00           C  
HETATM    7  C4  UNL     1      -3.920   0.254  -2.129  1.00  0.00           C  
HETATM    8  O4  UNL     1      -4.145  -0.777  -2.804  1.00  0.00           O  
HETATM    9  O5  UNL     1      -4.745   1.350  -2.311  1.00  0.00           O  
HETATM   10  C5  UNL     1      -3.423   0.582   0.206  1.00  0.00           C  
HETATM   11  O6  UNL     1      -4.670   1.175   0.076  1.00  0.00           O  
HETATM   12  C6  UNL     1      -3.498  -0.763   0.903  1.00  0.00           C  
HETATM   13  O7  UNL     1      -4.307  -0.723   2.030  1.00  0.00           O  
HETATM   14  C7  UNL     1      -2.065  -1.127   1.233  1.00  0.00           C  
HETATM   15  O8  UNL     1      -1.960  -2.342   1.877  1.00  0.00           O  
HETATM   16  C8  UNL     1       2.151   0.449  -0.144  1.00  0.00           C  
HETATM   17  C9  UNL     1       2.056   1.836  -0.018  1.00  0.00           C  
HETATM   18  N1  UNL     1       3.272   2.373  -0.041  1.00  0.00           N  
HETATM   19  C10 UNL     1       4.186   1.380  -0.179  1.00  0.00           C  
HETATM   20  C11 UNL     1       5.560   1.405  -0.256  1.00  0.00           C  
HETATM   21  C12 UNL     1       6.268   0.240  -0.398  1.00  0.00           C  
HETATM   22  C13 UNL     1       5.621  -0.974  -0.466  1.00  0.00           C  
HETATM   23  C14 UNL     1       4.246  -0.976  -0.387  1.00  0.00           C  
HETATM   24  C15 UNL     1       3.499   0.188  -0.243  1.00  0.00           C  
HETATM   25  H1  UNL     1      -0.842  -2.098  -0.193  1.00  0.00           H  
HETATM   26  H2  UNL     1      -2.150   1.152  -1.427  1.00  0.00           H  
HETATM   27  H3  UNL     1      -5.748   1.266  -2.155  1.00  0.00           H  
HETATM   28  H4  UNL     1      -2.743   1.269   0.747  1.00  0.00           H  
HETATM   29  H5  UNL     1      -5.236   0.795   0.812  1.00  0.00           H  
HETATM   30  H6  UNL     1      -3.855  -1.538   0.178  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.635  -1.661   2.196  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.655  -0.303   1.860  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.128  -2.800   1.607  1.00  0.00           H  
HETATM   34  H10 UNL     1       1.103   2.345   0.081  1.00  0.00           H  
HETATM   35  H11 UNL     1       3.521   3.382   0.032  1.00  0.00           H  
HETATM   36  H12 UNL     1       6.092   2.338  -0.206  1.00  0.00           H  
HETATM   37  H13 UNL     1       7.362   0.236  -0.461  1.00  0.00           H  
HETATM   38  H14 UNL     1       6.164  -1.905  -0.578  1.00  0.00           H  
HETATM   39  H15 UNL     1       3.699  -1.913  -0.437  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   16
CONECT    3    4
CONECT    4    5   14   25
CONECT    5    6
CONECT    6    7   10   26
CONECT    7    8    8    9
CONECT    9   27
CONECT   10   11   12   28
CONECT   11   29
CONECT   12   13   14   30
CONECT   13   31
CONECT   14   15   32
CONECT   15   33
CONECT   16   17   17   24
CONECT   17   18   34
CONECT   18   19   35
CONECT   19   20   20   24
CONECT   20   21   36
CONECT   21   22   22   37
CONECT   22   23   38
CONECT   23   24   24   39
END

HMDB0013189
     RDKit          3D
3-Indole carboxylic acid glucuronide
 39 41  0  0  0  0  0  0  0  0999 V2000
    1.3485   -1.7358   -0.2872 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0696   -0.5173   -0.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2614   -0.1485   -0.0571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2943   -1.0914   -0.0797 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1376   -0.9137   -1.1731 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7962    0.2906   -1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9201    0.2541   -2.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1454   -0.7774   -2.8039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7450    1.3500   -2.3107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4227    0.5823    0.2060 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6700    1.1749    0.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4985   -0.7629    0.9028 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3069   -0.7233    2.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0654   -1.1270    1.2325 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9601   -2.3417    1.8772 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1508    0.4485   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0564    1.8359   -0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2719    2.3727   -0.0409 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1863    1.3803   -0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5599    1.4045   -0.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2678    0.2399   -0.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6207   -0.9742   -0.4659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2457   -0.9759   -0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    0.1880   -0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8423   -2.0982   -0.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501    1.1519   -1.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7482    1.2663   -2.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7433    1.2694    0.7466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2356    0.7953    0.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8549   -1.5376    0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6354   -1.6615    2.1962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6552   -0.3026    1.8603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1279   -2.7998    1.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1027    2.3452    0.0810 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5205    3.3824    0.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0924    2.3380   -0.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3619    0.2359   -0.4607 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1636   -1.9050   -0.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6986   -1.9125   -0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 14  4  1  0
 24 16  1  0
 24 19  1  0
  4 25  1  6
  6 26  1  0
  9 27  1  0
 10 28  1  1
 11 29  1  0
 12 30  1  6
 13 31  1  0
 14 32  1  1
 15 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
 23 39  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-Indole carboxylate glucuronide	Generator
Indole-3-carboxylate glucuronide	HMDB
1H-Indole-3-carboxylate glucuronide	HMDB
1H-Indole-3-carboxylic acid glucuronide	HMDB
3-Indole carboxylic acid glucuronoside	HMDB
3-Indolecarboxylate glucuronide	HMDB
3-Indolecarboxylic acid glucuronide	HMDB
3-Indoleformate glucuronide	HMDB
3-Indoleformic acid glucuronide	HMDB
3-Indolylcarboxylate glucuronide	HMDB
3-Indolylcarboxylic acid glucuronide	HMDB
Indole-3 carboxylate glucuronide	HMDB
Indole-3-carboxilic acid-O-glucuronide	HMDB
Indole-3-carboxylic acid glucuronide	HMDB
Indole-3-carboxylic acid glucuronoside	HMDB
Indole-3-carboxylicacid glucuronide	HMDB
(3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(1H-indole-3-carbonyloxy)oxane-2-carboxylate	Generator

Chemical Formula

C₁₅H₁₅NO₈

Average Molecular Weight

337.2815

Monoisotopic Molecular Weight

337.079766461

IUPAC Name

(3S,4S,5R,6S)-3,4,5-trihydroxy-6-(1H-indole-3-carbonyloxy)oxane-2-carboxylic acid

Traditional Name

(3S,4S,5R,6S)-3,4,5-trihydroxy-6-(1H-indole-3-carbonyloxy)oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](O)[C@H](OC(=O)C2=CNC3=CC=CC=C23)OC([C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C15H15NO8/c17-9-10(18)12(13(20)21)23-15(11(9)19)24-14(22)7-5-16-8-4-2-1-3-6(7)8/h1-5,9-12,15-19H,(H,20,21)/t9-,10-,11+,12?,15-/m0/s1

InChI Key

BDNWJTRKUBXAGH-DOVARBIBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glucuronides

Alternative Parents

Substituents

1-o-glucuronide
O-glucuronide
Indolecarboxylic acid derivative
Indole
Indole or derivatives
Pyrrole-3-carboxylic acid or derivatives
Beta-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Monosaccharide
Oxane
Pyran
Substituted pyrrole
Benzenoid
Vinylogous amide
Pyrrole
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Azacycle
Carboxylic acid
Acetal
Oxacycle
Organic nitrogen compound
Organonitrogen compound
Alcohol
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

glucosiduronic acid (CHEBI:68486 )
O-acyl carbohydrate (CHEBI:68486 )
indolyl carbohydrate (CHEBI:68486 )

Ontology

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0013189)

Organ

Liver (HMDB: HMDB0013189)
Kidney (HMDB: HMDB0013189)

Excreta

Biofluid or Excreta

Urine (PMID: 22827565)

Source

Endogenous

Endogenous (HMDB: HMDB0013189)

Process

Not Available

Role

Biological role

Waste product (HMDB: HMDB0013189)

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	8.93 g/L	ALOGPS
logP	-0.14	ALOGPS
logP	-0.018	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.29	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	149.31 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.7 m³·mol⁻¹	ChemAxon
Polarizability	32.04 Å³	ChemAxon
Number of Rings	3	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]+	177.963	31661259
DarkChem	[M-H]-	168.806	31661259
DeepCCS	[M-2H]-	203.683	30932474
DeepCCS	[M+Na]+	178.706	30932474
AllCCS	[M+H]+	177.5	32859911
AllCCS	[M+H-H2O]+	174.4	32859911
AllCCS	[M+NH4]+	180.3	32859911
AllCCS	[M+Na]+	181.1	32859911
AllCCS	[M-H]-	173.4	32859911
AllCCS	[M+Na-2H]-	173.0	32859911
AllCCS	[M+HCOO]-	172.7	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.	4.7 minutes	32390414
Predicted by Siyang on May 30, 2022	10.7245 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.49 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1551.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	226.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	79.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	117.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	289.1 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	330.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	306.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	630.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	316.2 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	1134.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	247.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	226.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	400.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	205.9 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	225.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Indole carboxylic acid glucuronide	O[C@@H]1[C@@H](O)[C@H](OC(=O)C2=CNC3=CC=CC=C23)OC([C@H]1O)C(O)=O	4237.9	Standard polar	33892256
3-Indole carboxylic acid glucuronide	O[C@@H]1[C@@H](O)[C@H](OC(=O)C2=CNC3=CC=CC=C23)OC([C@H]1O)C(O)=O	2811.8	Standard non polar	33892256
3-Indole carboxylic acid glucuronide	O[C@@H]1[C@@H](O)[C@H](OC(=O)C2=CNC3=CC=CC=C23)OC([C@H]1O)C(O)=O	3371.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Indole carboxylic acid glucuronide,1TMS,isomer #1	C[Si](C)(C)O[C@H]1[C@H](O)C(C(=O)O)O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@@H]1O	3119.4	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,1TMS,isomer #2	C[Si](C)(C)O[C@H]1[C@H](OC(=O)C2=C[NH]C3=CC=CC=C23)OC(C(=O)O)[C@@H](O)[C@@H]1O	3112.6	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1C(C(=O)O)O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O)[C@H]1O	3118.8	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,1TMS,isomer #4	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O	3105.4	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,1TMS,isomer #5	C[Si](C)(C)N1C=C(C(=O)O[C@@H]2OC(C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)C2=CC=CC=C21	3119.0	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TMS,isomer #1	C[Si](C)(C)O[C@@H]1C(C(=O)O)O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O)[C@H]1O[Si](C)(C)C	3092.7	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TMS,isomer #10	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O	3047.2	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TMS,isomer #2	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	3080.9	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TMS,isomer #3	C[Si](C)(C)O[C@H]1[C@H](O)C(C(=O)O)O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@@H]1O[Si](C)(C)C	3109.0	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TMS,isomer #4	C[Si](C)(C)O[C@H]1[C@H](O)C(C(=O)O)O[C@@H](OC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@@H]1O	3071.1	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TMS,isomer #5	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O	3064.5	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TMS,isomer #6	C[Si](C)(C)O[C@@H]1C(C(=O)O)O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@H]1O	3092.5	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TMS,isomer #7	C[Si](C)(C)O[C@H]1[C@H](OC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C23)OC(C(=O)O)[C@@H](O)[C@@H]1O	3064.7	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TMS,isomer #8	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C	3081.6	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TMS,isomer #9	C[Si](C)(C)O[C@@H]1C(C(=O)O)O[C@@H](OC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O)[C@H]1O	3073.9	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TMS,isomer #1	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	3108.3	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TMS,isomer #10	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C	3085.6	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TMS,isomer #2	C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)C(C(=O)O)O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@@H]1O[Si](C)(C)C	3136.8	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TMS,isomer #3	C[Si](C)(C)O[C@@H]1C(C(=O)O)O[C@@H](OC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O)[C@H]1O[Si](C)(C)C	3098.1	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TMS,isomer #4	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	3099.5	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TMS,isomer #5	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	3085.3	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TMS,isomer #6	C[Si](C)(C)O[C@H]1[C@H](O)C(C(=O)O)O[C@@H](OC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@@H]1O[Si](C)(C)C	3108.8	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TMS,isomer #7	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	3106.0	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TMS,isomer #8	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O	3070.8	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TMS,isomer #9	C[Si](C)(C)O[C@@H]1C(C(=O)O)O[C@@H](OC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@H]1O	3104.7	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,4TMS,isomer #1	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	3191.6	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,4TMS,isomer #2	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	3148.5	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,4TMS,isomer #3	C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)C(C(=O)O)O[C@@H](OC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@@H]1O[Si](C)(C)C	3184.8	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,4TMS,isomer #4	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	3139.3	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,4TMS,isomer #5	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	3157.1	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,5TMS,isomer #1	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	3246.0	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,5TMS,isomer #1	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2916.3	Standard non polar	33892256
3-Indole carboxylic acid glucuronide,5TMS,isomer #1	C[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	3226.3	Standard polar	33892256
3-Indole carboxylic acid glucuronide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)C(C(=O)O)O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@@H]1O	3399.7	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](OC(=O)C2=C[NH]C3=CC=CC=C23)OC(C(=O)O)[C@@H](O)[C@@H]1O	3387.0	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1C(C(=O)O)O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O)[C@H]1O	3386.3	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O	3371.1	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N1C=C(C(=O)O[C@@H]2OC(C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)C2=CC=CC=C21	3370.5	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C(C(=O)O)O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3598.4	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O	3519.7	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3587.9	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)C(C(=O)O)O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@@H]1O[Si](C)(C)C(C)(C)C	3613.6	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)C(C(=O)O)O[C@@H](OC(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@@H]1O	3538.6	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	3573.6	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1C(C(=O)O)O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3601.5	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](OC(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)OC(C(=O)O)[C@@H](O)[C@@H]1O	3529.8	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3586.5	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@@H]1C(C(=O)O)O[C@@H](OC(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O)[C@H]1O	3537.6	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3790.9	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3715.1	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C(C(=O)O)O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@@H]1O[Si](C)(C)C(C)(C)C	3822.4	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1C(C(=O)O)O[C@@H](OC(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3721.6	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3791.6	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3697.1	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)C(C(=O)O)O[C@@H](OC(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@@H]1O[Si](C)(C)C(C)(C)C	3732.7	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3804.3	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	3687.2	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@@H]1C(C(=O)O)O[C@@H](OC(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3723.0	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	4002.8	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	3866.3	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)C(C(=O)O)O[C@@H](OC(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@@H]1O[Si](C)(C)C(C)(C)C	3900.5	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3859.5	Semi standard non polar	33892256
3-Indole carboxylic acid glucuronide,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)C1O[C@@H](OC(=O)C2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3895.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Indole carboxylic acid glucuronide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-9221000000-e405acbb88ebd4f37923	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Indole carboxylic acid glucuronide GC-MS (4 TMS) - 70eV, Positive	splash10-03di-4941047000-f01e76abc2e863b6a421	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Indole carboxylic acid glucuronide 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 - 3-Indole carboxylic acid glucuronide 10V, Positive-QTOF	splash10-03dl-0902000000-e8fb84e81fcefb88928b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Indole carboxylic acid glucuronide 20V, Positive-QTOF	splash10-0006-0900000000-c6aa02214865ae939df3	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Indole carboxylic acid glucuronide 40V, Positive-QTOF	splash10-00kf-1900000000-7c819f04717299b3f743	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Indole carboxylic acid glucuronide 10V, Negative-QTOF	splash10-03y3-1913000000-4ae8bab45fad6c393e9f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Indole carboxylic acid glucuronide 20V, Negative-QTOF	splash10-02t9-1900000000-18e5eb04fe891824393f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Indole carboxylic acid glucuronide 40V, Negative-QTOF	splash10-03xu-5900000000-af080777a9b1c93909a7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Indole carboxylic acid glucuronide 10V, Positive-QTOF	splash10-000l-0609000000-9768d5748961306bdf08	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Indole carboxylic acid glucuronide 20V, Positive-QTOF	splash10-01ox-0902000000-fe9a3cf27ec94e3aaf83	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Indole carboxylic acid glucuronide 40V, Positive-QTOF	splash10-00kf-1900000000-15a5ec877ba7065f42c6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Indole carboxylic acid glucuronide 10V, Negative-QTOF	splash10-014r-0509000000-642d74c686a5391c7534	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Indole carboxylic acid glucuronide 20V, Negative-QTOF	splash10-02t9-2932000000-0fefa625351cecfa36e0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Indole carboxylic acid glucuronide 40V, Negative-QTOF	splash10-014i-1900000000-088ab2e521f234147fe4	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22827565	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Type 2 diabetes mellitus or three or more major cardiovascular risk factors	24882253	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Cardiosvacular risk	Mar Garcia-A...	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

FDB029324

KNApSAcK ID

Not Available

Chemspider ID

28533205

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481645

PDB ID

Not Available

ChEBI ID

68486

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

HARTMANN F, FREIBERG E, RUGE W: [Indolepatterns in the urine of liver patients]. Klin Wochenschr. 1962 Jul 15;40:721-9. [PubMed:13905029 ]
Byrd DJ, Kochen W, Idzko D, Knorr E: The analysis of indolic tryptophan metabolites in human urine. Thin-layer chromatography and in situ quantitation. J Chromatogr. 1974 Jul 17;94(0):85-106. [PubMed:4844607 ]

Showing metabocard for 3-Indole carboxylic acid glucuronide (HMDB0013189)

MOL for HMDB0013189 (3-Indole carboxylic acid glucuronide)

3D MOL for HMDB0013189 (3-Indole carboxylic acid glucuronide)

3D SDF for HMDB0013189 (3-Indole carboxylic acid glucuronide)

3D-SDF for HMDB0013189 (3-Indole carboxylic acid glucuronide)

PDB for HMDB0013189 (3-Indole carboxylic acid glucuronide)

3D PDB for HMDB0013189 (3-Indole carboxylic acid glucuronide)

SMILES for HMDB0013189 (3-Indole carboxylic acid glucuronide)

INCHI for HMDB0013189 (3-Indole carboxylic acid glucuronide)

Structure for HMDB0013189 (3-Indole carboxylic acid glucuronide)

3D Structure for HMDB0013189 (3-Indole carboxylic acid glucuronide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra