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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-22 21:05:16 UTC

Update Date

2021-09-22 21:05:17 UTC

HMDB ID

HMDB0301785

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-O-(Indole-3-acetyl)-D-glucopyranose

Description

4-o-(indole-3-acetyl)-d-glucopyranose, also known as indole-3-acetyl-beta-1-D-glucose or B-D-glucopyranose, 1-(1h-indole-3-acetic acid), 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. 4-o-(indole-3-acetyl)-d-glucopyranose is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 4-o-(indole-3-acetyl)-d-glucopyranose can be found in corn, which makes 4-o-(indole-3-acetyl)-d-glucopyranose a potential biomarker for the consumption of this food product.

Structure

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

HMDB0301785
     RDKit          3D
4-O-(Indole-3-acetyl)-D-glucopyranose
 43 45  0  0  0  0  0  0  0  0999 V2000
   -0.8828    0.7736    1.3117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7555    1.3161    0.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9339    2.0419   -0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9930    1.1009   -0.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2326    0.7146   -2.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2468   -0.1608   -2.1950 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7031   -0.3715   -0.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6973   -1.1507   -0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9319   -1.1680    0.9364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1629   -0.3921    1.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1552    0.4021    1.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9204    0.4119   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4622    1.2029   -0.4448 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5923    0.5355    0.0877 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6639    1.3520    0.0694 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9138    0.8385    0.1813 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7864    1.1005   -1.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0460    0.5328   -0.8228 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -0.5955    0.6080 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1454   -0.6986    2.0076 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9319   -1.4844    0.0590 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4428   -2.5382   -0.7275 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8908   -0.7272   -0.7145 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7439   -1.5122   -0.8464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6284    2.7461   -1.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441    2.6672    0.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6895    1.0519   -3.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6593   -0.6298   -3.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3205   -1.7718   -1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7086   -1.7742    1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3494   -0.3985    2.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5367    1.0216    1.9411 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978    0.1713    1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4344    1.4443    0.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8671    2.1975   -1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3670    0.6516   -1.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2558   -0.1272   -1.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9896   -0.9860    0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542    0.1588    2.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4290   -1.9428    0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9141   -3.1968   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986   -0.4343   -1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -2.3731   -0.4325 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  1  0
 16 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  1
 16 34  1  1
 17 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  6
 20 39  1  0
 21 40  1  1
 22 41  1  0
 23 42  1  6
 24 43  1  0
M  END


  Mrv0541 02241212162D          

 24 26  0  0  0  0            999 V2000
   -0.0589   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7734   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7734   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0589   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6555   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6555   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4878   -2.2687    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2023   -1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2023   -1.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7857   -0.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5825   -0.6614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7961   -1.4583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4514    1.1595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4514    1.9845    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1659    2.3970    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.8804    1.9845    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.8804    1.1595    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1659    0.7470    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1659   -0.0780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5948    0.7470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7370    2.3970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1659    3.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5949    2.3970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7370    3.2220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  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
  9  2  1  0  0  0  0
  2  3  1  0  0  0  0
  7  3  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  2  0  0  0  0
 11 19  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  1  0  0  0
 17 20  1  6  0  0  0
 14 21  1  1  0  0  0
 15 22  1  6  0  0  0
 16 23  1  1  0  0  0
 21 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301785

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@H]1O[C@@H](OC(=O)CC2=CNC3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO7/c18-7-11-13(20)14(21)15(22)16(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/t11-,13-,14+,15-,16+/m1/s1

> <INCHI_KEY>
HHDMMUWDSFASNB-JZYAIQKZSA-N

> <FORMULA>
C16H19NO7

> <MOLECULAR_WEIGHT>
337.3246

> <EXACT_MASS>
337.116151967

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.709777696358522

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.02

> <JCHEM_LOGP>
-0.5583119949999996

> <ALOGPS_LOGS>
-1.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.189115728526989

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.195536206159124

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810936792926377

> <JCHEM_POLAR_SURFACE_AREA>
132.24

> <JCHEM_REFRACTIVITY>
80.88329999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.62e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
iaa-glucose

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301785
     RDKit          3D
4-O-(Indole-3-acetyl)-D-glucopyranose
 43 45  0  0  0  0  0  0  0  0999 V2000
   -0.8828    0.7736    1.3117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7555    1.3161    0.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9339    2.0419   -0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9930    1.1009   -0.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2326    0.7146   -2.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2468   -0.1608   -2.1950 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7031   -0.3715   -0.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6973   -1.1507   -0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9319   -1.1680    0.9364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1629   -0.3921    1.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1552    0.4021    1.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9204    0.4119   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4622    1.2029   -0.4448 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5923    0.5355    0.0877 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6639    1.3520    0.0694 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9138    0.8385    0.1813 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7864    1.1005   -1.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0460    0.5328   -0.8228 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -0.5955    0.6080 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1454   -0.6986    2.0076 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9319   -1.4844    0.0590 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4428   -2.5382   -0.7275 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8908   -0.7272   -0.7145 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7439   -1.5122   -0.8464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6284    2.7461   -1.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441    2.6672    0.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6895    1.0519   -3.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6593   -0.6298   -3.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3205   -1.7718   -1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7086   -1.7742    1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3494   -0.3985    2.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5367    1.0216    1.9411 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978    0.1713    1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4344    1.4443    0.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8671    2.1975   -1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3670    0.6516   -1.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2558   -0.1272   -1.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9896   -0.9860    0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542    0.1588    2.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4290   -1.9428    0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9141   -3.1968   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986   -0.4343   -1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -2.3731   -0.4325 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  1  0
 16 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  1
 16 34  1  1
 17 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  6
 20 39  1  0
 21 40  1  1
 22 41  1  0
 23 42  1  6
 24 43  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.110  -1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.444  -1.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.444  -3.465   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.110  -4.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.224  -3.465   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.224  -1.925   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -2.777  -4.235   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -4.111  -3.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.111  -1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.200  -0.836   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.687  -1.235   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -7.086  -2.722   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -6.443   2.164   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -6.443   3.704   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.776   4.474   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.110   3.704   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.110   2.164   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.776   1.394   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -7.776  -0.146   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0     -10.444   1.394   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -5.109   4.474   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -7.776   6.014   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0     -10.444   4.474   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.109   6.014   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    9    3                                                  
CONECT    3    4    2    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    3    8                                                       
CONECT    8    7    9                                                       
CONECT    9    2    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   19                                                  
CONECT   12   11                                                            
CONECT   13   14   18                                                       
CONECT   14   13   15   21                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   20                                                  
CONECT   18   13   17   19                                                  
CONECT   19   11   18                                                       
CONECT   20   17                                                            
CONECT   21   14   24                                                       
CONECT   22   15                                                            
CONECT   23   16                                                            
CONECT   24   21                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0301785
HETATM    1  O1  UNL     1      -0.883   0.774   1.312  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.755   1.316   0.178  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.934   2.042  -0.416  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.993   1.101  -0.824  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.233   0.715  -2.131  1.00  0.00           C  
HETATM    6  N1  UNL     1      -4.247  -0.161  -2.195  1.00  0.00           N  
HETATM    7  C5  UNL     1      -4.703  -0.372  -0.923  1.00  0.00           C  
HETATM    8  C6  UNL     1      -5.697  -1.151  -0.400  1.00  0.00           C  
HETATM    9  C7  UNL     1      -5.932  -1.168   0.936  1.00  0.00           C  
HETATM   10  C8  UNL     1      -5.163  -0.392   1.788  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.155   0.402   1.293  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.920   0.412  -0.091  1.00  0.00           C  
HETATM   13  O2  UNL     1       0.462   1.203  -0.445  1.00  0.00           O  
HETATM   14  C11 UNL     1       1.592   0.535   0.088  1.00  0.00           C  
HETATM   15  O3  UNL     1       2.664   1.352   0.069  1.00  0.00           O  
HETATM   16  C12 UNL     1       3.914   0.839   0.181  1.00  0.00           C  
HETATM   17  C13 UNL     1       4.786   1.100  -1.055  1.00  0.00           C  
HETATM   18  O4  UNL     1       6.046   0.533  -0.823  1.00  0.00           O  
HETATM   19  C14 UNL     1       4.008  -0.596   0.608  1.00  0.00           C  
HETATM   20  O5  UNL     1       4.145  -0.699   2.008  1.00  0.00           O  
HETATM   21  C15 UNL     1       2.932  -1.484   0.059  1.00  0.00           C  
HETATM   22  O6  UNL     1       3.443  -2.538  -0.728  1.00  0.00           O  
HETATM   23  C16 UNL     1       1.891  -0.727  -0.714  1.00  0.00           C  
HETATM   24  O7  UNL     1       0.744  -1.512  -0.846  1.00  0.00           O  
HETATM   25  H1  UNL     1      -1.628   2.746  -1.213  1.00  0.00           H  
HETATM   26  H2  UNL     1      -2.344   2.667   0.415  1.00  0.00           H  
HETATM   27  H3  UNL     1      -2.689   1.052  -3.022  1.00  0.00           H  
HETATM   28  H4  UNL     1      -4.659  -0.630  -3.030  1.00  0.00           H  
HETATM   29  H5  UNL     1      -6.321  -1.772  -1.030  1.00  0.00           H  
HETATM   30  H6  UNL     1      -6.709  -1.774   1.403  1.00  0.00           H  
HETATM   31  H7  UNL     1      -5.349  -0.398   2.869  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.537   1.022   1.941  1.00  0.00           H  
HETATM   33  H9  UNL     1       1.398   0.171   1.137  1.00  0.00           H  
HETATM   34  H10 UNL     1       4.434   1.444   0.988  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.867   2.198  -1.221  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.367   0.652  -1.976  1.00  0.00           H  
HETATM   37  H13 UNL     1       6.256  -0.127  -1.556  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.990  -0.986   0.193  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.354   0.159   2.416  1.00  0.00           H  
HETATM   40  H16 UNL     1       2.429  -1.943   0.962  1.00  0.00           H  
HETATM   41  H17 UNL     1       3.914  -3.197  -0.156  1.00  0.00           H  
HETATM   42  H18 UNL     1       2.299  -0.434  -1.693  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.917  -2.373  -0.432  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
CONECT   16   17   19   34
CONECT   17   18   35   36
CONECT   18   37
CONECT   19   20   21   38
CONECT   20   39
CONECT   21   22   23   40
CONECT   22   41
CONECT   23   24   42
CONECT   24   43
END

HMDB0301785
     RDKit          3D
4-O-(Indole-3-acetyl)-D-glucopyranose
 43 45  0  0  0  0  0  0  0  0999 V2000
   -0.8828    0.7736    1.3117 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7555    1.3161    0.1781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9339    2.0419   -0.4159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9930    1.1009   -0.8238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2326    0.7146   -2.1315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2468   -0.1608   -2.1950 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7031   -0.3715   -0.9234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6973   -1.1507   -0.3998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9319   -1.1680    0.9364 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1629   -0.3921    1.7878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1552    0.4021    1.2929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9204    0.4119   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4622    1.2029   -0.4448 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5923    0.5355    0.0877 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6639    1.3520    0.0694 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9138    0.8385    0.1813 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7864    1.1005   -1.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0460    0.5328   -0.8228 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0083   -0.5955    0.6080 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1454   -0.6986    2.0076 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9319   -1.4844    0.0590 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4428   -2.5382   -0.7275 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8908   -0.7272   -0.7145 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7439   -1.5122   -0.8464 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6284    2.7461   -1.2131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441    2.6672    0.4145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6895    1.0519   -3.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6593   -0.6298   -3.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3205   -1.7718   -1.0300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7086   -1.7742    1.4026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3494   -0.3985    2.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5367    1.0216    1.9411 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3978    0.1713    1.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4344    1.4443    0.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8671    2.1975   -1.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3670    0.6516   -1.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2558   -0.1272   -1.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9896   -0.9860    0.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542    0.1588    2.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4290   -1.9428    0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9141   -3.1968   -0.1558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986   -0.4343   -1.6926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -2.3731   -0.4325 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  1  0
 16 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  1
 16 34  1  1
 17 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  6
 20 39  1  0
 21 40  1  1
 22 41  1  0
 23 42  1  6
 24 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-O-(indol-3-yl)Acetyl-beta-D-glucose	ChEBI
1-O-(Indole-3-acetyl)-beta-1-D-glucose	ChEBI
1-O-indol-3-Ylacetyl-beta-D-glucose	ChEBI
1-O-indol-3-Ylacetylglucose	ChEBI
beta-D-Glucopyranose, 1-(1H-indole-3-acetate)	ChEBI
Iaa-glucose	ChEBI
Indole-3-acetic acid beta-D-glucoside	ChEBI
Indole-3-acetyl-beta-1-D-glucose	ChEBI
Indole-3-acetyl-beta-1-D-glucoside	ChEBI
1-O-(indol-3-yl)Acetyl-b-D-glucose	Generator
1-O-(indol-3-yl)Acetyl-β-D-glucose	Generator
1-O-(Indole-3-acetyl)-b-1-D-glucose	Generator
1-O-(Indole-3-acetyl)-β-1-D-glucose	Generator
1-O-indol-3-Ylacetyl-b-D-glucose	Generator
1-O-indol-3-Ylacetyl-β-D-glucose	Generator
b-D-Glucopyranose, 1-(1H-indole-3-acetate)	Generator
b-D-Glucopyranose, 1-(1H-indole-3-acetic acid)	Generator
beta-D-Glucopyranose, 1-(1H-indole-3-acetic acid)	Generator
Β-D-glucopyranose, 1-(1H-indole-3-acetate)	Generator
Β-D-glucopyranose, 1-(1H-indole-3-acetic acid)	Generator
Indole-3-acetate b-D-glucoside	Generator
Indole-3-acetate beta-D-glucoside	Generator
Indole-3-acetate β-D-glucoside	Generator
Indole-3-acetic acid b-D-glucoside	Generator
Indole-3-acetic acid β-D-glucoside	Generator
Indole-3-acetyl-b-1-D-glucose	Generator
Indole-3-acetyl-β-1-D-glucose	Generator
Indole-3-acetyl-b-1-D-glucoside	Generator
Indole-3-acetyl-β-1-D-glucoside	Generator
1-O-(indol-3-Ylacetyl)-b-D-glucose	Generator
1-O-(indol-3-Ylacetyl)-β-D-glucose	Generator

Chemical Formula

C₁₆H₁₉NO₇

Average Molecular Weight

337.3246

Monoisotopic Molecular Weight

337.116151967

IUPAC Name

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

Traditional Name

iaa-glucose

CAS Registry Number

52703-89-6

SMILES

OC[C@H]1O[C@@H](OC(=O)CC2=CNC3=CC=CC=C23)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C16H19NO7/c18-7-11-13(20)14(21)15(22)16(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/t11-,13-,14+,15-,16+/m1/s1

InChI Key

HHDMMUWDSFASNB-JZYAIQKZSA-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
Secondary alcohol
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Oxacycle
Polyol
Azacycle
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Carbonyl group
Alcohol
Primary alcohol
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

indolyl carbohydrate (CHEBI:17990 )
indoleacetic acid ester conjugate (CHEBI:17990 )

Ontology

Not Available

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

Process

Not Available

Role

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)	12.2	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	31.71 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]+	179.682	32859911
AllCCS	[M+H-H2O]+	176.632	32859911
AllCCS	[M+Na]+	183.31	32859911
AllCCS	[M+NH4]+	182.501	32859911
AllCCS	[M-H]-	176.651	32859911
AllCCS	[M+Na-2H]-	176.502	32859911
AllCCS	[M+HCOO]-	176.472	32859911
DeepCCS	[M-2H]-	205.364	30932474
DeepCCS	[M+Na]+	180.606	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-O-(Indole-3-acetyl)-D-glucopyranose,5TMS,isomer #1	C[Si](C)(C)OC[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	3176.0	Semi standard non polar	33892256
4-O-(Indole-3-acetyl)-D-glucopyranose,5TMS,isomer #1	C[Si](C)(C)OC[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	2950.8	Standard non polar	33892256
4-O-(Indole-3-acetyl)-D-glucopyranose,5TMS,isomer #1	C[Si](C)(C)OC[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	3213.8	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 - 4-O-(Indole-3-acetyl)-D-glucopyranose 10V, Positive-QTOF	splash10-0bvr-0902000000-0687c8913b28a5dc41d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-(Indole-3-acetyl)-D-glucopyranose 20V, Positive-QTOF	splash10-0arr-0900000000-71497166c9dc020d734c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-(Indole-3-acetyl)-D-glucopyranose 40V, Positive-QTOF	splash10-053r-2900000000-71d824c7b4fe5f7d205e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-(Indole-3-acetyl)-D-glucopyranose 10V, Negative-QTOF	splash10-0a4i-0902000000-453018a3206763f500ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-(Indole-3-acetyl)-D-glucopyranose 20V, Negative-QTOF	splash10-05fr-1900000000-72ae2dc14bdeb57d9e7c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-(Indole-3-acetyl)-D-glucopyranose 40V, Negative-QTOF	splash10-0abc-6900000000-de636a4246bdcb7ba5a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-(Indole-3-acetyl)-D-glucopyranose 10V, Positive-QTOF	splash10-0019-0908000000-caf98e9c7cd5ad00b61d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-(Indole-3-acetyl)-D-glucopyranose 20V, Positive-QTOF	splash10-06gj-2792000000-719176d609074dfc1c2b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-(Indole-3-acetyl)-D-glucopyranose 40V, Positive-QTOF	splash10-001i-4900000000-b00f4d484a3ef3b6a106	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-(Indole-3-acetyl)-D-glucopyranose 10V, Negative-QTOF	splash10-002r-0906000000-01901d00dd9b6772f342	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-(Indole-3-acetyl)-D-glucopyranose 20V, Negative-QTOF	splash10-0a6r-2900000000-d985579fbe048c317199	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-O-(Indole-3-acetyl)-D-glucopyranose 40V, Negative-QTOF	splash10-003r-4900000000-ecbbc823b3a734a00ad8	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

FDB030935

KNApSAcK ID

Not Available

Chemspider ID

389235

KEGG Compound ID

C04197

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

17990

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 4-O-(Indole-3-acetyl)-D-glucopyranose (HMDB0301785)

MOL for HMDB0301785 (4-O-(Indole-3-acetyl)-D-glucopyranose)

3D MOL for HMDB0301785 (4-O-(Indole-3-acetyl)-D-glucopyranose)

3D SDF for HMDB0301785 (4-O-(Indole-3-acetyl)-D-glucopyranose)

3D-SDF for HMDB0301785 (4-O-(Indole-3-acetyl)-D-glucopyranose)

PDB for HMDB0301785 (4-O-(Indole-3-acetyl)-D-glucopyranose)

3D PDB for HMDB0301785 (4-O-(Indole-3-acetyl)-D-glucopyranose)

SMILES for HMDB0301785 (4-O-(Indole-3-acetyl)-D-glucopyranose)

INCHI for HMDB0301785 (4-O-(Indole-3-acetyl)-D-glucopyranose)

Structure for HMDB0301785 (4-O-(Indole-3-acetyl)-D-glucopyranose)

3D Structure for HMDB0301785 (4-O-(Indole-3-acetyl)-D-glucopyranose)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra