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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-04-09 21:18:57 UTC

Update Date

2021-09-14 15:39:03 UTC

HMDB ID

HMDB0060001

Secondary Accession Numbers

HMDB60001

Metabolite Identification

Common Name

Indole-3-acetic-acid-O-glucuronide

Description

Indole-3-acetic-acid-O-glucuronide belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Indole-3-acetic-acid-O-glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0060001
     RDKit          3D
Indole-3-acetic-acid-O-glucuronide
 42 44  0  0  0  0  0  0  0  0999 V2000
    0.6057   -0.0230   -1.5460 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5759   -0.8479   -0.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072   -1.5618   -0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223   -0.6898    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3070   -0.4647    1.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3370    0.3638    1.5045 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6705    0.7120    0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6574    1.5370   -0.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7863    1.7278   -1.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9041    1.0710   -2.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9081    0.2383   -1.9357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8010    0.0645   -0.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6332   -1.0701    0.0241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8482   -0.4200   -0.3191 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2226    0.3410    0.7975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375    0.9502    0.4897 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6232    2.0981    1.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6608    2.8258    1.3032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6771    2.3848    2.3675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5327   -0.0796    0.6817 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6143    0.2695   -0.1041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0646   -1.4635    0.3024 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7865   -2.2057    1.4495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8908   -1.4301   -0.6462 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3199   -1.2485   -1.9654 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5516   -2.2170    0.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1727   -2.2351   -1.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8311   -0.9015    2.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8165    0.6934    2.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3450    2.0494    0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5712    2.3836   -1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0327    1.2424   -3.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2196   -0.2753   -2.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6425    0.2719   -1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4158    1.3213   -0.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9676    3.0710    2.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8792   -0.1029    1.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4834   -0.0883   -1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8937   -1.9765   -0.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0632   -1.7664    1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4400   -2.4539   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7261   -2.0949   -2.3144 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 12  4  1  0
 24 14  1  0
 12  7  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  6
 16 35  1  6
 19 36  1  0
 20 37  1  1
 21 38  1  0
 22 39  1  6
 23 40  1  0
 24 41  1  6
 25 42  1  0
M  END


  Mrv1652304062013142D          

 25 27  0  0  0  0            999 V2000
   -1.4143    0.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1288   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1288   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4143   -1.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998   -0.8839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6998   -0.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0848   -1.1389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5697   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0848    0.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3398    0.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1367    1.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3502    1.9910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7200    0.6107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1471    2.2045    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8616    3.4420    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1471    3.0295    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8616    1.7920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5760    2.2045    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5760    3.0295    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2905    1.7920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0050    2.2045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2905    0.9670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2905    3.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8616    4.2670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326    3.4420    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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  6  2  0  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 14 12  1  1  0  0  0
 16 14  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 18 20  1  1  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 19 23  1  6  0  0  0
 15 24  1  1  0  0  0
 16 25  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0060001

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@@H]1[C@@H](O)[C@H](OC(=O)CC2=CNC3=C2C=CC=C3)O[C@@H]([C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO8/c18-10(5-7-6-17-9-4-2-1-3-8(7)9)24-16-13(21)11(19)12(20)14(25-16)15(22)23/h1-4,6,11-14,16-17,19-21H,5H2,(H,22,23)/t11-,12-,13+,14-,16+/m0/s1

> <INCHI_KEY>
BPTLUNCVRGWZSW-JHZZJYKESA-N

> <FORMULA>
C16H17NO8

> <MOLECULAR_WEIGHT>
351.3081

> <EXACT_MASS>
351.095416525

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.63202467388555

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-(1H-indol-3-yl)acetyl]oxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-0.11

> <JCHEM_LOGP>
-0.23803745699999987

> <ALOGPS_LOGS>
-1.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.212046230646518

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.388049170538595

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6868986995677924

> <JCHEM_POLAR_SURFACE_AREA>
149.31

> <JCHEM_REFRACTIVITY>
80.7507

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-(1H-indol-3-yl)acetyl]oxy}oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060001
     RDKit          3D
Indole-3-acetic-acid-O-glucuronide
 42 44  0  0  0  0  0  0  0  0999 V2000
    0.6057   -0.0230   -1.5460 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5759   -0.8479   -0.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072   -1.5618   -0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223   -0.6898    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3070   -0.4647    1.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3370    0.3638    1.5045 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6705    0.7120    0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6574    1.5370   -0.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7863    1.7278   -1.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9041    1.0710   -2.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9081    0.2383   -1.9357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8010    0.0645   -0.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6332   -1.0701    0.0241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8482   -0.4200   -0.3191 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2226    0.3410    0.7975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375    0.9502    0.4897 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6232    2.0981    1.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6608    2.8258    1.3032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6771    2.3848    2.3675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5327   -0.0796    0.6817 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6143    0.2695   -0.1041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0646   -1.4635    0.3024 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7865   -2.2057    1.4495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8908   -1.4301   -0.6462 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3199   -1.2485   -1.9654 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5516   -2.2170    0.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1727   -2.2351   -1.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8311   -0.9015    2.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8165    0.6934    2.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3450    2.0494    0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5712    2.3836   -1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0327    1.2424   -3.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2196   -0.2753   -2.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6425    0.2719   -1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4158    1.3213   -0.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9676    3.0710    2.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8792   -0.1029    1.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4834   -0.0883   -1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8937   -1.9765   -0.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0632   -1.7664    1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4400   -2.4539   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7261   -2.0949   -2.3144 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 12  4  1  0
 24 14  1  0
 12  7  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  6
 16 35  1  6
 19 36  1  0
 20 37  1  1
 21 38  1  0
 22 39  1  6
 23 40  1  0
 24 41  1  6
 25 42  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0      -2.640   0.660   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.974  -0.110   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.974  -1.650   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.640  -2.420   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.306  -1.650   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.306  -0.110   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       0.158  -2.126   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.063  -0.880   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.158   0.366   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.634   1.830   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.122   2.229   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.520   3.717   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.211   1.140   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.008   4.115   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.342   6.425   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.008   5.655   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.342   3.345   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.675   4.115   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.675   5.655   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.009   3.345   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.343   4.115   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.009   1.805   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.009   6.425   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.342   7.965   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.674   6.425   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    7    6                                                  
CONECT    6    1    5    9                                                  
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    6    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   14                                                       
CONECT   13   11                                                            
CONECT   14   12   16   17                                                  
CONECT   15   16   19   24                                                  
CONECT   16   14   15   25                                                  
CONECT   17   14   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   15   23                                                  
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   19                                                            
CONECT   24   15                                                            
CONECT   25   16                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0060001
HETATM    1  O1  UNL     1       0.606  -0.023  -1.546  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.576  -0.848  -0.613  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.807  -1.562  -0.208  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.922  -0.690   0.163  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.307  -0.465   1.490  1.00  0.00           C  
HETATM    6  N1  UNL     1       4.337   0.364   1.505  1.00  0.00           N  
HETATM    7  C5  UNL     1       4.670   0.712   0.260  1.00  0.00           C  
HETATM    8  C6  UNL     1       5.657   1.537  -0.204  1.00  0.00           C  
HETATM    9  C7  UNL     1       5.786   1.728  -1.566  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.904   1.071  -2.408  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.908   0.238  -1.936  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.801   0.064  -0.569  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.633  -1.070   0.024  1.00  0.00           O  
HETATM   14  C11 UNL     1      -1.848  -0.420  -0.319  1.00  0.00           C  
HETATM   15  O3  UNL     1      -2.223   0.341   0.797  1.00  0.00           O  
HETATM   16  C12 UNL     1      -3.437   0.950   0.490  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.623   2.098   1.404  1.00  0.00           C  
HETATM   18  O4  UNL     1      -4.661   2.826   1.303  1.00  0.00           O  
HETATM   19  O5  UNL     1      -2.677   2.385   2.367  1.00  0.00           O  
HETATM   20  C14 UNL     1      -4.533  -0.080   0.682  1.00  0.00           C  
HETATM   21  O6  UNL     1      -5.614   0.269  -0.104  1.00  0.00           O  
HETATM   22  C15 UNL     1      -4.065  -1.463   0.302  1.00  0.00           C  
HETATM   23  O7  UNL     1      -3.786  -2.206   1.450  1.00  0.00           O  
HETATM   24  C16 UNL     1      -2.891  -1.430  -0.646  1.00  0.00           C  
HETATM   25  O8  UNL     1      -3.320  -1.249  -1.965  1.00  0.00           O  
HETATM   26  H1  UNL     1       1.552  -2.217   0.659  1.00  0.00           H  
HETATM   27  H2  UNL     1       2.173  -2.235  -1.035  1.00  0.00           H  
HETATM   28  H3  UNL     1       2.831  -0.901   2.356  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.817   0.693   2.390  1.00  0.00           H  
HETATM   30  H5  UNL     1       6.345   2.049   0.453  1.00  0.00           H  
HETATM   31  H6  UNL     1       6.571   2.384  -1.913  1.00  0.00           H  
HETATM   32  H7  UNL     1       5.033   1.242  -3.466  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.220  -0.275  -2.582  1.00  0.00           H  
HETATM   34  H9  UNL     1      -1.643   0.272  -1.185  1.00  0.00           H  
HETATM   35  H10 UNL     1      -3.416   1.321  -0.557  1.00  0.00           H  
HETATM   36  H11 UNL     1      -1.968   3.071   2.207  1.00  0.00           H  
HETATM   37  H12 UNL     1      -4.879  -0.103   1.740  1.00  0.00           H  
HETATM   38  H13 UNL     1      -5.483  -0.088  -1.018  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.894  -1.977  -0.226  1.00  0.00           H  
HETATM   40  H15 UNL     1      -3.063  -1.766   1.978  1.00  0.00           H  
HETATM   41  H16 UNL     1      -2.440  -2.454  -0.619  1.00  0.00           H  
HETATM   42  H17 UNL     1      -3.726  -2.095  -2.314  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4   26   27
CONECT    4    5    5   12
CONECT    5    6   28
CONECT    6    7   29
CONECT    7    8    8   12
CONECT    8    9   30
CONECT    9   10   10   31
CONECT   10   11   32
CONECT   11   12   12   33
CONECT   13   14
CONECT   14   15   24   34
CONECT   15   16
CONECT   16   17   20   35
CONECT   17   18   18   19
CONECT   19   36
CONECT   20   21   22   37
CONECT   21   38
CONECT   22   23   24   39
CONECT   23   40
CONECT   24   25   41
CONECT   25   42
END

HMDB0060001
     RDKit          3D
Indole-3-acetic-acid-O-glucuronide
 42 44  0  0  0  0  0  0  0  0999 V2000
    0.6057   -0.0230   -1.5460 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5759   -0.8479   -0.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072   -1.5618   -0.2084 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9223   -0.6898    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3070   -0.4647    1.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3370    0.3638    1.5045 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6705    0.7120    0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6574    1.5370   -0.2045 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7863    1.7278   -1.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9041    1.0710   -2.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9081    0.2383   -1.9357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8010    0.0645   -0.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6332   -1.0701    0.0241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8482   -0.4200   -0.3191 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2226    0.3410    0.7975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375    0.9502    0.4897 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6232    2.0981    1.4044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6608    2.8258    1.3032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6771    2.3848    2.3675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5327   -0.0796    0.6817 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6143    0.2695   -0.1041 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0646   -1.4635    0.3024 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7865   -2.2057    1.4495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8908   -1.4301   -0.6462 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3199   -1.2485   -1.9654 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5516   -2.2170    0.6590 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1727   -2.2351   -1.0350 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8311   -0.9015    2.3559 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8165    0.6934    2.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3450    2.0494    0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5712    2.3836   -1.9130 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0327    1.2424   -3.4664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2196   -0.2753   -2.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6425    0.2719   -1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4158    1.3213   -0.5574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9676    3.0710    2.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8792   -0.1029    1.7401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4834   -0.0883   -1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8937   -1.9765   -0.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0632   -1.7664    1.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4400   -2.4539   -0.6190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7261   -2.0949   -2.3144 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 12  4  1  0
 24 14  1  0
 12  7  1  0
  3 26  1  0
  3 27  1  0
  5 28  1  0
  6 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 14 34  1  6
 16 35  1  6
 19 36  1  0
 20 37  1  1
 21 38  1  0
 22 39  1  6
 23 40  1  0
 24 41  1  6
 25 42  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-{[2-(1H-indol-3-yl)acetyl]oxy}oxane-2-carboxylate	Generator

Chemical Formula

C₁₆H₁₇NO₈

Average Molecular Weight

351.3081

Monoisotopic Molecular Weight

351.095416525

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-(1H-indol-3-yl)acetyl]oxy}oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[2-(1H-indol-3-yl)acetyl]oxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](O)[C@H](OC(=O)CC2=CNC3=C2C=CC=C3)O[C@@H]([C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C16H17NO8/c18-10(5-7-6-17-9-4-2-1-3-8(7)9)24-16-13(21)11(19)12(20)14(25-16)15(22)23/h1-4,6,11-14,16-17,19-21H,5H2,(H,22,23)/t11-,12-,13+,14-,16+/m0/s1

InChI Key

BPTLUNCVRGWZSW-JHZZJYKESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
C-glucuronide
Glucuronic acid or derivatives
C-glycosyl compound
Glycosyl compound
Monocyclic monoterpenoid
Monoterpenoid
P-menthane monoterpenoid
Beta-hydroxy acid
Pyran
Oxane
Hydroxy acid
Secondary alcohol
Polyol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Ether
Dialkyl ether
Carboxylic acid
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.26 g/L	ALOGPS
logP	-0.11	ALOGPS
logP	-0.24	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	3.39	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	5	ChemAxon
Refractivity	80.75 m³·mol⁻¹	ChemAxon
Polarizability	33.63 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]+	182.954	31661259
DarkChem	[M-H]-	179.975	31661259
DeepCCS	[M+H]+	179.285	30932474
DeepCCS	[M-H]-	176.889	30932474
DeepCCS	[M-2H]-	209.786	30932474
DeepCCS	[M+Na]+	185.198	30932474
AllCCS	[M+H]+	181.3	32859911
AllCCS	[M+H-H2O]+	178.4	32859911
AllCCS	[M+NH4]+	184.1	32859911
AllCCS	[M+Na]+	184.9	32859911
AllCCS	[M-H]-	177.9	32859911
AllCCS	[M+Na-2H]-	177.6	32859911
AllCCS	[M+HCOO]-	177.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Indole-3-acetic-acid-O-glucuronide	O[C@@H]1[C@@H](O)[C@H](OC(=O)CC2=CNC3=C2C=CC=C3)O[C@@H]([C@H]1O)C(O)=O	4459.0	Standard polar	33892256
Indole-3-acetic-acid-O-glucuronide	O[C@@H]1[C@@H](O)[C@H](OC(=O)CC2=CNC3=C2C=CC=C3)O[C@@H]([C@H]1O)C(O)=O	2749.6	Standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide	O[C@@H]1[C@@H](O)[C@H](OC(=O)CC2=CNC3=C2C=CC=C3)O[C@@H]([C@H]1O)C(O)=O	3323.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Indole-3-acetic-acid-O-glucuronide,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)O[C@H](C(=O)O)[C@H]1O	3125.0	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,1TMS,isomer #2	C[Si](C)(C)O[C@H]1[C@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)O[C@H](C(=O)O)[C@@H](O)[C@@H]1O	3133.6	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@H]1O	3107.5	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,1TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O	3101.7	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,1TMS,isomer #5	C[Si](C)(C)N1C=C(CC(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)C2=CC=CC=C21	3116.6	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TMS,isomer #1	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](C(=O)O)O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@@H]1O[Si](C)(C)C	3123.7	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TMS,isomer #10	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O	3088.5	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	3089.5	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@H]1O[Si](C)(C)C	3106.8	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](OC(=O)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)O[C@H](C(=O)O)[C@H]1O	3107.8	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O	3090.7	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@H]1O	3113.3	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TMS,isomer #7	C[Si](C)(C)O[C@H]1[C@H](OC(=O)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)O[C@H](C(=O)O)[C@@H](O)[C@@H]1O	3109.4	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TMS,isomer #8	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C	3096.1	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TMS,isomer #9	C[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O)[C@H]1O	3104.7	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)O[C@H](C(=O)O)[C@H]1O[Si](C)(C)C	3172.7	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TMS,isomer #10	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C	3127.7	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	3158.8	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TMS,isomer #3	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](C(=O)O)O[C@@H](OC(=O)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@@H]1O[Si](C)(C)C	3142.4	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	3157.1	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	3111.7	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O)[C@H]1O[Si](C)(C)C	3132.8	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TMS,isomer #7	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	3154.9	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TMS,isomer #8	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O	3114.2	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TMS,isomer #9	C[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)[C@H](O[Si](C)(C)C)[C@H]1O	3135.1	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=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	3246.7	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,4TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C)[C@H](OC(=O)CC2=CN([Si](C)(C)C)C3=CC=CC=C23)O[C@H](C(=O)O)[C@H]1O[Si](C)(C)C	3205.9	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=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	3168.7	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=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	3177.1	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,4TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=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	3180.5	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=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	3269.8	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=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	2967.1	Standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=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	3320.4	Standard polar	33892256
Indole-3-acetic-acid-O-glucuronide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)O[C@H](C(=O)O)[C@H]1O	3411.7	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)O[C@H](C(=O)O)[C@@H](O)[C@@H]1O	3417.3	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@H]1O	3393.4	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O	3392.7	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N1C=C(CC(=O)O[C@@H]2O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]2O)C2=CC=CC=C21	3369.8	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](C(=O)O)O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@@H]1O[Si](C)(C)C(C)(C)C	3656.7	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O	3553.2	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	3619.3	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3627.6	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](OC(=O)CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)O[C@H](C(=O)O)[C@H]1O	3562.2	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	3627.2	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3640.2	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](OC(=O)CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)O[C@H](C(=O)O)[C@@H](O)[C@@H]1O	3577.9	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	3627.4	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@H](O)[C@H]1O	3560.9	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC(=O)CC2=C[NH]C3=CC=CC=C23)O[C@H](C(=O)O)[C@H]1O[Si](C)(C)C(C)(C)C	3881.3	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=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	3745.5	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=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	3846.5	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](C(=O)O)O[C@@H](OC(=O)CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)[C@@H]1O[Si](C)(C)C(C)(C)C	3775.9	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=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	3847.0	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=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	3731.5	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)CC2=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	3751.3	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=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	3866.4	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=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	3749.0	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](C(=O)O)O[C@@H](OC(=O)CC2=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	3765.4	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=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	4063.4	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](OC(=O)CC2=CN([Si](C)(C)C(C)(C)C)C3=CC=CC=C23)O[C@H](C(=O)O)[C@H]1O[Si](C)(C)C(C)(C)C	3943.1	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=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	3911.9	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=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	3907.0	Semi standard non polar	33892256
Indole-3-acetic-acid-O-glucuronide,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H]1O[C@@H](OC(=O)CC2=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	3946.1	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 - Indole-3-acetic-acid-O-glucuronide GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-6912000000-966fe33f20413c2cf0b6	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indole-3-acetic-acid-O-glucuronide GC-MS (4 TMS) - 70eV, Positive	splash10-001i-1911022000-db6d3d519dfbdce478a3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Indole-3-acetic-acid-O-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 - Indole-3-acetic-acid-O-glucuronide 10V, Positive-QTOF	splash10-057i-0903000000-af77dc75dc3504a6106a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetic-acid-O-glucuronide 20V, Positive-QTOF	splash10-0a7i-0900000000-e8f7a98e0d79d19e48b5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetic-acid-O-glucuronide 40V, Positive-QTOF	splash10-0560-1900000000-1d39e6133188cfc327fd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetic-acid-O-glucuronide 10V, Negative-QTOF	splash10-0a4i-0902000000-e44c053e9952cb27b3dd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetic-acid-O-glucuronide 20V, Negative-QTOF	splash10-05gi-1900000000-3a0dc031516b57da09c4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetic-acid-O-glucuronide 40V, Negative-QTOF	splash10-0ab9-4900000000-1e87aa9b67aa9ab6b05e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetic-acid-O-glucuronide 10V, Positive-QTOF	splash10-0udi-0409000000-7f1318088c1419de3eb1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetic-acid-O-glucuronide 20V, Positive-QTOF	splash10-001i-0965000000-0425ea9418b6f8a841d2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetic-acid-O-glucuronide 40V, Positive-QTOF	splash10-0f89-2910000000-36b303d7aad5193319af	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetic-acid-O-glucuronide 10V, Negative-QTOF	splash10-0kn9-0905000000-f3954fc68bed806232a9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetic-acid-O-glucuronide 20V, Negative-QTOF	splash10-0a4i-1900000000-451a22b5f2263739e98f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Indole-3-acetic-acid-O-glucuronide 40V, Negative-QTOF	splash10-00or-3900000000-bb15326e5cf0ff47f5bf	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

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

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

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124202110

PDB ID

Not Available

ChEBI ID

89622

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

van der Hooft JJ, de Vos RC, Mihaleva V, Bino RJ, Ridder L, de Roo N, Jacobs DM, van Duynhoven JP, Vervoort J: Structural elucidation and quantification of phenolic conjugates present in human urine after tea intake. Anal Chem. 2012 Aug 21;84(16):7263-71. doi: 10.1021/ac3017339. Epub 2012 Aug 2. [PubMed:22827565 ]

Showing metabocard for Indole-3-acetic-acid-O-glucuronide (HMDB0060001)

MOL for HMDB0060001 (Indole-3-acetic-acid-O-glucuronide)

3D MOL for HMDB0060001 (Indole-3-acetic-acid-O-glucuronide)

3D SDF for HMDB0060001 (Indole-3-acetic-acid-O-glucuronide)

3D-SDF for HMDB0060001 (Indole-3-acetic-acid-O-glucuronide)

PDB for HMDB0060001 (Indole-3-acetic-acid-O-glucuronide)

3D PDB for HMDB0060001 (Indole-3-acetic-acid-O-glucuronide)

SMILES for HMDB0060001 (Indole-3-acetic-acid-O-glucuronide)

INCHI for HMDB0060001 (Indole-3-acetic-acid-O-glucuronide)

Structure for HMDB0060001 (Indole-3-acetic-acid-O-glucuronide)

3D Structure for HMDB0060001 (Indole-3-acetic-acid-O-glucuronide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra