NP-MRD: Showing NP-Card for (2-hydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h-indol-3-yl)acetic acid (NP0175109)

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Record Information

Version

1.0

Created at

2022-09-03 12:29:41 UTC

Updated at

2022-09-03 12:29:41 UTC

NP-MRD ID

NP0175109

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2-hydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h-indol-3-yl)acetic acid

Description

7-Hydroxy-2-oxindole-3-acetic acid beta-D-glucoside, also known as 7-(b-D-glucosyloxy)-2-oxindole-3-acetate, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. 7-Hydroxy-2-oxindole-3-acetic acid beta-D-glucoside is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2-hydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h-indol-3-yl)acetic acid is found in Arabidopsis thaliana. It was first documented in 1985 (PMID: 4044604). Based on a literature review very few articles have been published on 7-hydroxy-2-oxindole-3-acetic acid beta-D-glucoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032214292D          

 26 28  0  0  1  0            999 V2000
   -0.1781   -3.1062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.6021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668    3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    2.1896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  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
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  1  0  0  0
 10 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
  9 26  1  0  0  0  0
  5 26  1  0  0  0  0
M  END

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
    7.1830    1.2266   -1.3384 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3638    0.9262   -0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6027    1.3875    0.8406 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2101    0.1127   -0.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2028   -0.0881    0.3326 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5736    1.1277    0.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2333    2.2664    1.3906 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3005    1.0145    0.7252 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9237   -0.2217    0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6433   -0.7112   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4362    0.0679    0.1525 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7789   -0.1873   -0.0337 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3582    0.8237   -0.8054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6686    0.5875   -1.1240 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2485    1.9285   -1.5970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5929    2.4292   -2.6927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5441    0.1301   -0.0042 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6443   -0.5166   -0.5828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8773   -0.6989    1.0418 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6441   -0.6380    2.2096 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5115   -0.1015    1.3133 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8269   -0.7344    2.3160 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5563   -1.9632   -0.7045 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7052   -2.6860   -0.9663 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9576   -2.1905   -0.6760 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0699   -0.9348   -0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5047    1.6805    1.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5662   -0.9126   -1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6450    0.4989   -1.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6863   -0.5832    1.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0978    3.1769    0.9329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0267   -1.1687   -0.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7296   -0.1600   -1.9692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3424    1.8338   -1.7678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1331    2.6109   -0.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8636    3.0135   -2.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9850    1.0253    0.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2821   -0.6953    0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7600   -1.7256    0.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1410   -1.5019    2.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6853    0.9868    1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0330   -1.6843    2.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4328   -2.3426   -0.9279 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6455   -3.6706   -1.4124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8748   -2.7380   -0.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  6  2  0
  6  7  1  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  5 26  1  0
 26 25  2  0
 25 24  1  0
 24 23  2  0
 12 21  1  0
 21 22  1  0
 21 19  1  0
 19 20  1  0
 19 17  1  0
 17 18  1  0
 17 14  1  0
 23 10  1  0
 26  9  1  0
 16 36  1  0
 15 34  1  0
 15 35  1  0
 14 33  1  6
 12 32  1  6
  7 31  1  0
  5 30  1  1
  4 28  1  0
  4 29  1  0
  3 27  1  0
 25 45  1  0
 24 44  1  0
 23 43  1  0
 21 41  1  1
 22 42  1  0
 19 39  1  6
 20 40  1  0
 17 37  1  1
 18 38  1  0
M  END


  Mrv1652309032214292D          

 26 28  0  0  1  0            999 V2000
   -0.1781   -3.1062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4752   -1.7084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3523    2.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.6021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0668    3.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    3.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    2.1896    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4957    2.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.3646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4957    0.9521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  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
  6  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 11  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  1  0  0  0
 10 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
  9 26  1  0  0  0  0
  5 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0175109

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=C3N=C(O)C(CC(O)=O)C3=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO9/c18-5-9-12(21)13(22)14(23)16(26-9)25-8-3-1-2-6-7(4-10(19)20)15(24)17-11(6)8/h1-3,7,9,12-14,16,18,21-23H,4-5H2,(H,17,24)(H,19,20)/t7?,9-,12-,13+,14-,16-/m1/s1

> <INCHI_KEY>
GJXGLYODFWLYHO-PNNKGAHQSA-N

> <FORMULA>
C16H19NO9

> <MOLECULAR_WEIGHT>
369.326

> <EXACT_MASS>
369.105981196

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.75927872154137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(2-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H-indol-3-yl)acetic acid

> <ALOGPS_LOGP>
-1.27

> <JCHEM_LOGP>
-1.1048133793333332

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.391713660543161

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.333843103788873

> <JCHEM_PKA_STRONGEST_BASIC>
-0.49971470193675505

> <JCHEM_POLAR_SURFACE_AREA>
169.26999999999998

> <JCHEM_REFRACTIVITY>
85.3062

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.97e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H-indol-3-yl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  O   UNK     0      -0.333  -5.798   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.887  -3.189   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.258   4.087   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.591   4.857   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.591   6.397   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.258   7.167   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.925   4.087   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.259   4.857   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.925   2.547   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      10.259   1.777   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.591   1.777   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   26                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   26                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   12   22                                                  
CONECT   22   21                                                            
CONECT   23   10   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25    9    5                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
7-(beta-D-Glucosyloxy)-2-oxindole-3-acetic acid	ChEBI
7-Hydroxy-2-oxindole-3-acetic acid beta-glucoside	ChEBI
7-Hydroxy-2-oxindole-3-acetic acid glucoside	ChEBI
7-(b-D-Glucosyloxy)-2-oxindole-3-acetate	Generator
7-(b-D-Glucosyloxy)-2-oxindole-3-acetic acid	Generator
7-(beta-D-Glucosyloxy)-2-oxindole-3-acetate	Generator
7-(Β-D-glucosyloxy)-2-oxindole-3-acetate	Generator
7-(Β-D-glucosyloxy)-2-oxindole-3-acetic acid	Generator
7-Hydroxy-2-oxindole-3-acetate b-glucoside	Generator
7-Hydroxy-2-oxindole-3-acetate beta-glucoside	Generator
7-Hydroxy-2-oxindole-3-acetate β-glucoside	Generator
7-Hydroxy-2-oxindole-3-acetic acid b-glucoside	Generator
7-Hydroxy-2-oxindole-3-acetic acid β-glucoside	Generator
7-Hydroxy-2-oxindole-3-acetate glucoside	Generator
7-Hydroxy-2-oxindole-3-acetate b-D-glucoside	Generator
7-Hydroxy-2-oxindole-3-acetate beta-D-glucoside	Generator
7-Hydroxy-2-oxindole-3-acetate β-D-glucoside	Generator
7-Hydroxy-2-oxindole-3-acetic acid b-D-glucoside	Generator
7-Hydroxy-2-oxindole-3-acetic acid β-D-glucoside	Generator

Chemical Formula

C₁₆H₁₉NO₉

Average Mass

369.3260 Da

Monoisotopic Mass

369.10598 Da

IUPAC Name

2-(2-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H-indol-3-yl)acetic acid

Traditional Name

(2-hydroxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3H-indol-3-yl)acetic acid

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=C3N=C(O)C(CC(O)=O)C3=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C16H19NO9/c18-5-9-12(21)13(22)14(23)16(26-9)25-8-3-1-2-6-7(4-10(19)20)15(24)17-11(6)8/h1-3,7,9,12-14,16,18,21-23H,4-5H2,(H,17,24)(H,19,20)/t7?,9-,12-,13+,14-,16-/m1/s1

InChI Key

GJXGLYODFWLYHO-PNNKGAHQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arabidopsis thaliana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
Indolyl carboxylic acid derivative
O-glycosyl compound
Indole
Indole or derivatives
Dihydroindole
Benzenoid
Monosaccharide
Oxane
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Lactam
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Acetal
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Primary alcohol
Organic oxide
Alcohol
Organic nitrogen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-1.3	ALOGPS
logP	-1.1	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.33	ChemAxon
pKa (Strongest Basic)	-0.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	169.27 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	85.31 m³·mol⁻¹	ChemAxon
Polarizability	34.76 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

76962938

KEGG Compound ID

Not Available

BioCyc ID

7-HYDROXY-2-OXINDOLE-3-ACETIC-ACID-GLUCO

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44159515

PDB ID

Not Available

ChEBI ID

136944

Good Scents ID

Not Available

References

General References

Nonhebel HM, Kruse LI, Bandurski RS: Indole-3-acetic acid catabolism in Zea mays seedlings. Metabolic conversion of oxindole-3-acetic acid to 7-hydroxy-2-oxindole-3-acetic acid 7'-O-beta-D-glucopyranoside. J Biol Chem. 1985 Oct 15;260(23):12685-9. [PubMed:4044604 ]
LOTUS database [Link]

Showing NP-Card for (2-hydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h-indol-3-yl)acetic acid (NP0175109)

MOL for NP0175109 ((2-hydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h-indol-3-yl)acetic acid)

3D MOL for NP0175109 ((2-hydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h-indol-3-yl)acetic acid)

3D SDF for NP0175109 ((2-hydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h-indol-3-yl)acetic acid)

3D-SDF for NP0175109 ((2-hydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h-indol-3-yl)acetic acid)

PDB for NP0175109 ((2-hydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h-indol-3-yl)acetic acid)

3D PDB for NP0175109 ((2-hydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h-indol-3-yl)acetic acid)

SMILES for NP0175109 ((2-hydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h-indol-3-yl)acetic acid)

INCHI for NP0175109 ((2-hydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h-indol-3-yl)acetic acid)

Structure for NP0175109 ((2-hydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h-indol-3-yl)acetic acid)

3D Structure for NP0175109 ((2-hydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3h-indol-3-yl)acetic acid)