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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 09:25:20 UTC

Update Date

2021-09-24 09:25:20 UTC

HMDB ID

HMDB0304390

Secondary Accession Numbers

None

Metabolite Identification

Common Name

indole-3-acetyl-beta-4-D-glucose

Description

Indole-3-acetyl-beta-4-d-glucose belongs to indole-3-acetic acid derivatives class of compounds. Those are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. Indole-3-acetyl-beta-4-d-glucose is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Indole-3-acetyl-beta-4-d-glucose can be found in a number of food items such as tamarind, black-eyed pea, sweet potato, and sourdough, which makes indole-3-acetyl-beta-4-d-glucose a potential biomarker for the consumption of these food products.

Structure

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

HMDB0304390
     RDKit          3D
indole-3-acetyl-beta-4-D-glucose
 43 45  0  0  0  0  0  0  0  0999 V2000
    0.6524    0.9015    0.5885 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289    0.6918   -0.6393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5623    0.6629   -1.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8575    0.8988   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6149    2.0514   -0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7288    1.8548   -0.1783 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7139    0.5955    0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5585   -0.1514    1.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -1.4574    1.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1288   -2.0588    0.9935 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765   -1.3096    0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5690    0.0013   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8774    0.5053   -0.9826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9871    0.5221   -0.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5483   -0.8862   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123   -1.8175    0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9666   -1.5751    1.5076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878   -1.0838    0.7060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6414   -0.2212    0.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9840    0.2023    1.8675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4658    0.9085   -0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0093    0.5827   -1.6358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0922    1.4152   -0.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8615    1.7180   -1.9167 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4068    1.4365   -2.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6516   -0.3117   -2.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3557    2.9667   -1.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4824    2.5398    0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4900    0.2915    1.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9808   -2.0349    2.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023   -3.0922    1.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3852   -1.8011   -0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6701    0.7126    0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7985   -1.0898   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5433   -1.6351   -0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843   -2.8922    0.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7800   -1.5715    2.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5209   -0.8228    0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3450   -0.6021    2.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1276    1.7452   -0.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0303   -0.3970   -1.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9756    2.4113   -0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1307    1.1958   -2.2930 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
 15 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12  4  1  0
 23 14  1  0
 12  7  1  0
  3 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
 24 43  1  0
M  END

  Mrv1533005141521452D          

 24 26  0  0  0  0            999 V2000
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    1.7103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2673    1.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8194    1.2687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5644    0.4841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6263    1.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1784    0.8271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8813    2.2248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6882    2.3964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3292    2.8379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9702    3.2795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1633    3.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7575    0.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 17  1  0  0  0  0
  7 20  2  0  0  0  0
  1  5  2  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0304390

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1OC(O)C(O)C(O)C1OC(=O)CC1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO7/c18-7-11-15(13(20)14(21)16(22)23-11)24-12(19)5-8-6-17-10-4-2-1-3-9(8)10/h1-4,6,11,13-18,20-22H,5,7H2

> <INCHI_KEY>
XSNPKRVRWPBMKE-UHFFFAOYSA-N

> <FORMULA>
C16H19NO7

> <MOLECULAR_WEIGHT>
337.328

> <EXACT_MASS>
337.116151956

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.171942358521704

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 2-(1H-indol-3-yl)acetate

> <ALOGPS_LOGP>
0.02

> <JCHEM_LOGP>
-0.5583119949999995

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.873268628022618

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.304723874431339

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9817959747176657

> <JCHEM_POLAR_SURFACE_AREA>
132.24

> <JCHEM_REFRACTIVITY>
80.88330000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.66e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 2-(1H-indol-3-yl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304390
     RDKit          3D
indole-3-acetyl-beta-4-D-glucose
 43 45  0  0  0  0  0  0  0  0999 V2000
    0.6524    0.9015    0.5885 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289    0.6918   -0.6393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5623    0.6629   -1.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8575    0.8988   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6149    2.0514   -0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7288    1.8548   -0.1783 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7139    0.5955    0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5585   -0.1514    1.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -1.4574    1.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1288   -2.0588    0.9935 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765   -1.3096    0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5690    0.0013   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8774    0.5053   -0.9826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9871    0.5221   -0.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5483   -0.8862   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123   -1.8175    0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9666   -1.5751    1.5076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878   -1.0838    0.7060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6414   -0.2212    0.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9840    0.2023    1.8675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4658    0.9085   -0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0093    0.5827   -1.6358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0922    1.4152   -0.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8615    1.7180   -1.9167 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4068    1.4365   -2.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6516   -0.3117   -2.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3557    2.9667   -1.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4824    2.5398    0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4900    0.2915    1.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9808   -2.0349    2.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023   -3.0922    1.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3852   -1.8011   -0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6701    0.7126    0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7985   -1.0898   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5433   -1.6351   -0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843   -2.8922    0.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7800   -1.5715    2.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5209   -0.8228    0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3450   -0.6021    2.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1276    1.7452   -0.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0303   -0.3970   -1.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9756    2.4113   -0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1307    1.1958   -2.2930 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
 15 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12  4  1  0
 23 14  1  0
 12  7  1  0
  3 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
 24 43  1  0
M  END

HEADER    PROTEIN                                 14-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-15         0                                  
HETATM    1  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.250   1.728   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.726   3.192   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.232   3.513   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.263   2.368   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.787   0.904   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -6.769   2.688   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -7.800   1.544   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -7.245   4.153   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -8.751   4.473   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -6.215   5.297   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.708   4.977   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.678   6.122   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.171   5.802   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.281   0.583   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6    1                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18    9                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
CONECT   20    7                                                            
CONECT   21    4   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23    3                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0304390
HETATM    1  O1  UNL     1       0.652   0.902   0.588  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.429   0.692  -0.639  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.562   0.663  -1.595  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.858   0.899  -0.917  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.615   2.051  -0.917  1.00  0.00           C  
HETATM    6  N1  UNL     1       4.729   1.855  -0.178  1.00  0.00           N  
HETATM    7  C5  UNL     1       4.714   0.596   0.305  1.00  0.00           C  
HETATM    8  C6  UNL     1       5.558  -0.151   1.098  1.00  0.00           C  
HETATM    9  C7  UNL     1       5.294  -1.457   1.451  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.129  -2.059   0.994  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.277  -1.310   0.194  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.569   0.001  -0.144  1.00  0.00           C  
HETATM   13  O2  UNL     1      -0.877   0.505  -0.983  1.00  0.00           O  
HETATM   14  C11 UNL     1      -1.987   0.522  -0.117  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.548  -0.886  -0.162  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.412  -1.817   0.204  1.00  0.00           C  
HETATM   17  O3  UNL     1      -0.967  -1.575   1.508  1.00  0.00           O  
HETATM   18  O4  UNL     1      -3.588  -1.084   0.706  1.00  0.00           O  
HETATM   19  C14 UNL     1      -4.641  -0.221   0.581  1.00  0.00           C  
HETATM   20  O5  UNL     1      -4.984   0.202   1.867  1.00  0.00           O  
HETATM   21  C15 UNL     1      -4.466   0.909  -0.369  1.00  0.00           C  
HETATM   22  O6  UNL     1      -5.009   0.583  -1.636  1.00  0.00           O  
HETATM   23  C16 UNL     1      -3.092   1.415  -0.554  1.00  0.00           C  
HETATM   24  O7  UNL     1      -2.862   1.718  -1.917  1.00  0.00           O  
HETATM   25  H1  UNL     1       1.407   1.436  -2.394  1.00  0.00           H  
HETATM   26  H2  UNL     1       1.652  -0.312  -2.126  1.00  0.00           H  
HETATM   27  H3  UNL     1       3.356   2.967  -1.428  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.482   2.540   0.001  1.00  0.00           H  
HETATM   29  H5  UNL     1       6.490   0.291   1.479  1.00  0.00           H  
HETATM   30  H6  UNL     1       5.981  -2.035   2.085  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.902  -3.092   1.263  1.00  0.00           H  
HETATM   32  H8  UNL     1       2.385  -1.801  -0.143  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.670   0.713   0.947  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.799  -1.090  -1.230  1.00  0.00           H  
HETATM   35  H11 UNL     1      -0.543  -1.635  -0.462  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.684  -2.892   0.059  1.00  0.00           H  
HETATM   37  H13 UNL     1      -1.780  -1.571   2.074  1.00  0.00           H  
HETATM   38  H14 UNL     1      -5.521  -0.823   0.230  1.00  0.00           H  
HETATM   39  H15 UNL     1      -5.345  -0.602   2.330  1.00  0.00           H  
HETATM   40  H16 UNL     1      -5.128   1.745  -0.012  1.00  0.00           H  
HETATM   41  H17 UNL     1      -5.030  -0.397  -1.775  1.00  0.00           H  
HETATM   42  H18 UNL     1      -2.976   2.411  -0.032  1.00  0.00           H  
HETATM   43  H19 UNL     1      -2.131   1.196  -2.293  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4   25   26
CONECT    4    5    5   12
CONECT    5    6   27
CONECT    6    7   28
CONECT    7    8    8   12
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11   31
CONECT   11   12   12   32
CONECT   13   14
CONECT   14   15   23   33
CONECT   15   16   18   34
CONECT   16   17   35   36
CONECT   17   37
CONECT   18   19
CONECT   19   20   21   38
CONECT   20   39
CONECT   21   22   23   40
CONECT   22   41
CONECT   23   24   42
CONECT   24   43
END

HMDB0304390
     RDKit          3D
indole-3-acetyl-beta-4-D-glucose
 43 45  0  0  0  0  0  0  0  0999 V2000
    0.6524    0.9015    0.5885 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4289    0.6918   -0.6393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5623    0.6629   -1.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8575    0.8988   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6149    2.0514   -0.9172 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7288    1.8548   -0.1783 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7139    0.5955    0.3047 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5585   -0.1514    1.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -1.4574    1.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1288   -2.0588    0.9935 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2765   -1.3096    0.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5690    0.0013   -0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8774    0.5053   -0.9826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9871    0.5221   -0.1174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5483   -0.8862   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4123   -1.8175    0.2039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9666   -1.5751    1.5076 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5878   -1.0838    0.7060 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6414   -0.2212    0.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9840    0.2023    1.8675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4658    0.9085   -0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0093    0.5827   -1.6358 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0922    1.4152   -0.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8615    1.7180   -1.9167 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4068    1.4365   -2.3942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6516   -0.3117   -2.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3557    2.9667   -1.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4824    2.5398    0.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4900    0.2915    1.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9808   -2.0349    2.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9023   -3.0922    1.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3852   -1.8011   -0.1434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6701    0.7126    0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7985   -1.0898   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5433   -1.6351   -0.4620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843   -2.8922    0.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7800   -1.5715    2.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5209   -0.8228    0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3450   -0.6021    2.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1276    1.7452   -0.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0303   -0.3970   -1.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9756    2.4113   -0.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1307    1.1958   -2.2930 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
 15 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12  4  1  0
 23 14  1  0
 12  7  1  0
  3 25  1  0
  3 26  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 11 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  0
 24 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,5,6-Trihydroxy-2-(hydroxymethyl)oxan-3-yl 2-(1H-indol-3-yl)acetic acid	Generator

Chemical Formula

C₁₆H₁₉NO₇

Average Molecular Weight

337.328

Monoisotopic Molecular Weight

337.116151956

IUPAC Name

4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 2-(1H-indol-3-yl)acetate

Traditional Name

4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl 2-(1H-indol-3-yl)acetate

CAS Registry Number

Not Available

SMILES

OCC1OC(O)C(O)C(O)C1OC(=O)CC1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1S/C16H19NO7/c18-7-11-15(13(20)14(21)16(22)23-11)24-12(19)5-8-6-17-10-4-2-1-3-9(8)10/h1-4,6,11,13-18,20-22H,5,7H2

InChI Key

XSNPKRVRWPBMKE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indole-3-acetic acid derivatives

Alternative Parents

Substituents

Indole-3-acetic acid derivative
Hexose monosaccharide
3-alkylindole
Indole
Monosaccharide
Oxane
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Carboxylic acid ester
Hemiacetal
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Polyol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Alcohol
Organic nitrogen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (INDOLE-3-ACETYL-BETA-4-D-GLUCOSE )

Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.02	ALOGPS
logP	-0.56	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	132.24 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.88 m³·mol⁻¹	ChemAxon
Polarizability	33.17 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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
AllCCS	[M+H]+	179.686	32859911
AllCCS	[M+H-H2O]+	176.636	32859911
AllCCS	[M+Na]+	183.314	32859911
AllCCS	[M+NH4]+	182.505	32859911
AllCCS	[M-H]-	176.651	32859911
AllCCS	[M+Na-2H]-	176.502	32859911
AllCCS	[M+HCOO]-	176.472	32859911
DeepCCS	[M+H]+	172.43	30932474
DeepCCS	[M-H]-	170.072	30932474
DeepCCS	[M-2H]-	203.2	30932474
DeepCCS	[M+Na]+	178.523	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
indole-3-acetyl-beta-4-D-glucose,5TMS,isomer #1	C[Si](C)(C)OCC1OC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1OC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	3097.5	Semi standard non polar	33892256
indole-3-acetyl-beta-4-D-glucose,5TMS,isomer #1	C[Si](C)(C)OCC1OC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1OC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	2914.1	Standard non polar	33892256
indole-3-acetyl-beta-4-D-glucose,5TMS,isomer #1	C[Si](C)(C)OCC1OC(O[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1OC(=O)CC1=CN([Si](C)(C)C)C2=CC=CC=C12	3199.8	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - indole-3-acetyl-beta-4-D-glucose 10V, Positive-QTOF	splash10-059i-0809000000-fa9c2554a856cc727aca	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - indole-3-acetyl-beta-4-D-glucose 20V, Positive-QTOF	splash10-06si-0902000000-24db95d4e84a7de55a4c	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - indole-3-acetyl-beta-4-D-glucose 40V, Positive-QTOF	splash10-06si-2900000000-210a26615a4db3c4c127	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - indole-3-acetyl-beta-4-D-glucose 10V, Negative-QTOF	splash10-000i-0739000000-9e8abe7ad7907ac0e34b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - indole-3-acetyl-beta-4-D-glucose 20V, Negative-QTOF	splash10-07or-2911000000-e662269878901a3bd7b5	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - indole-3-acetyl-beta-4-D-glucose 40V, Negative-QTOF	splash10-05fr-2900000000-f58ee8649d27e956fc62	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - indole-3-acetyl-beta-4-D-glucose 10V, Positive-QTOF	splash10-0079-0419000000-41c6d5fda3542ec7825a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - indole-3-acetyl-beta-4-D-glucose 20V, Positive-QTOF	splash10-001i-1952000000-9c995f7d797edda3153d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - indole-3-acetyl-beta-4-D-glucose 40V, Positive-QTOF	splash10-03e9-7970000000-4298cc3cc5171bf92bbe	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - indole-3-acetyl-beta-4-D-glucose 10V, Negative-QTOF	splash10-0a4r-0903000000-12e0105218132e396fd8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - indole-3-acetyl-beta-4-D-glucose 20V, Negative-QTOF	splash10-0a4i-0900000000-b12b61f2da45efea26e1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - indole-3-acetyl-beta-4-D-glucose 40V, Negative-QTOF	splash10-0059-1920000000-437ddcefcca479a7aac4	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030936

KNApSAcK ID

Not Available

Chemspider ID

24785418

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for indole-3-acetyl-beta-4-D-glucose (HMDB0304390)

MOL for HMDB0304390 (indole-3-acetyl-beta-4-D-glucose)

3D MOL for HMDB0304390 (indole-3-acetyl-beta-4-D-glucose)

3D SDF for HMDB0304390 (indole-3-acetyl-beta-4-D-glucose)

3D-SDF for HMDB0304390 (indole-3-acetyl-beta-4-D-glucose)

PDB for HMDB0304390 (indole-3-acetyl-beta-4-D-glucose)

3D PDB for HMDB0304390 (indole-3-acetyl-beta-4-D-glucose)

SMILES for HMDB0304390 (indole-3-acetyl-beta-4-D-glucose)

INCHI for HMDB0304390 (indole-3-acetyl-beta-4-D-glucose)

Structure for HMDB0304390 (indole-3-acetyl-beta-4-D-glucose)

3D Structure for HMDB0304390 (indole-3-acetyl-beta-4-D-glucose)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra