NP-MRD: Showing NP-Card for tryptophan n-glucoside (NP0157621)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-02 15:02:38 UTC

Updated at

2022-09-02 15:02:38 UTC

NP-MRD ID

NP0157621

Secondary Accession Numbers

None

Natural Product Identification

Common Name

tryptophan n-glucoside

Description

Tryptophan N-glucoside belongs to the class of organic compounds known as 1-pyranosylindoles. These are nucleoside and nucleotide analogs with a structure that consists of an indole base which is N-substituted at the 1-position with a pyranose moiety. Nucleotide analogues contain a phosphate group linked to the C5 carbon atom of the pyranose. Tryptophan N-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. tryptophan n-glucoside is found in Malus pumila. tryptophan n-glucoside was first documented in 2000 (PMID: 11052755). Based on a literature review very few articles have been published on tryptophan N-glucoside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217022D          

 26 28  0  0  1  0            999 V2000
    2.2428   -2.5916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    0.0000 C   0  0  1  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
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0768    0.9256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    1.7103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9851    1.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739    2.3234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1190    3.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809    2.1518    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7329    2.7649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    1.3672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2428    1.1957    0.0000 O   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
    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
    1.1809   -3.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -4.1608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  1  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  4 23  1  0  0  0  0
 18 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
    5.4745   -2.1895    0.0071 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2807   -1.4455   -0.4676 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3069   -1.2913    0.6383 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0688   -0.5727    0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8526   -1.1707    0.0201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0829   -0.2433   -0.1669 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4399   -0.5966   -0.5555 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1876    0.4595   -0.9989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4438   -0.0098   -1.3226 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2279    0.9840   -2.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4224    2.1903   -1.5103 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2036   -0.4215   -0.1050 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7103   -1.7326   -0.2563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2395   -0.4888    1.0854 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7597    0.8010    1.2917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0610   -1.3314    0.6135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4908   -2.6030    0.2632 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4678    0.9418    0.0611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0466    2.2175    0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6995    3.3570    0.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0291    3.1623    0.6584 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5444    1.8850    0.6950 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7847    0.7756    0.4016 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7802   -0.1631   -0.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0754    0.6073   -1.7020 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0599    0.3019   -0.7060 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2072   -3.1804    0.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1999   -2.0269   -0.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974   -2.0951   -1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7768   -0.8864    1.5759 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0255   -2.3469    0.9524 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7369   -2.2600   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4087   -1.3402   -1.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2934   -0.9098   -1.9755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2242    0.5827   -2.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7191    1.1971   -3.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5934    2.6986   -1.3399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0602    0.2183    0.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7802   -2.1152    0.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7274   -0.9232    1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3687    1.4917    0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3800   -1.4333    1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3437   -2.7586   -0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0802    2.3363   -0.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2722    4.3493    0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6895    4.0000    0.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5830    1.6907    0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4825    0.2879    0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  6 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
  2 24  1  0
 24 26  1  0
 24 25  2  0
 23  4  1  0
 16  7  1  0
 23 18  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  6
  3 30  1  0
  3 31  1  0
  5 32  1  0
  7 33  1  6
  9 34  1  6
 10 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  1
 13 39  1  0
 14 40  1  1
 15 41  1  0
 16 42  1  1
 17 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 26 48  1  0
M  END


  Mrv1652309022217022D          

 26 28  0  0  1  0            999 V2000
    2.2428   -2.5916    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -2.7631    0.0000 C   0  0  1  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
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.7541    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0768    0.9256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781    1.7103    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9851    1.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2400    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739    2.3234    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1190    3.1080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809    2.1518    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7329    2.7649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358    1.3672    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2428    1.1957    0.0000 O   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
    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
    1.1809   -3.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -4.1608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  1  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  4 23  1  0  0  0  0
 18 23  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157621

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2=CC=CC=C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22N2O7/c18-10(17(24)25)5-8-6-19(11-4-2-1-3-9(8)11)16-15(23)14(22)13(21)12(7-20)26-16/h1-4,6,10,12-16,20-23H,5,7,18H2,(H,24,25)/t10-,12+,13+,14-,15+,16+/m0/s1

> <INCHI_KEY>
ZHBHZDMTVVJASV-JOSVURMMSA-N

> <FORMULA>
C17H22N2O7

> <MOLECULAR_WEIGHT>
366.37

> <EXACT_MASS>
366.142701056

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.95880418189917

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-{1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H-indol-3-yl}propanoic acid

> <ALOGPS_LOGP>
-1.93

> <JCHEM_LOGP>
-3.2764115800575673

> <ALOGPS_LOGS>
-1.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.360886584760593

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9718663712495381

> <JCHEM_PKA_STRONGEST_BASIC>
9.387887808128765

> <JCHEM_POLAR_SURFACE_AREA>
158.4

> <JCHEM_REFRACTIVITY>
88.76159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-3-{1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]indol-3-yl}propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  N   UNK     0       4.187  -4.838   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.680  -5.158   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.650   1.408   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.143   1.728   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.333   3.192   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.839   3.513   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.315   4.977   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.698   4.337   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.222   5.802   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.204   4.017   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.235   5.161   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.680   2.552   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.187   2.232   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.204  -6.622   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.235  -7.767   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.698  -6.943   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    7   17                                                  
CONECT   17   16                                                            
CONECT   18    6   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22    4   18                                                  
CONECT   24    2   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
L-Tryptophan N-glucopyranoside	ChEBI
L-Tryptophan N-glucoside	ChEBI
Tryptophan-N-glucoside	MeSH
N(1)-Glucospyranosyltryptophan	MeSH

Chemical Formula

C₁₇H₂₂N₂O₇

Average Mass

366.3700 Da

Monoisotopic Mass

366.14270 Da

IUPAC Name

(2S)-2-amino-3-{1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-1H-indol-3-yl}propanoic acid

Traditional Name

(2S)-2-amino-3-{1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]indol-3-yl}propanoic acid

CAS Registry Number

Not Available

SMILES

N[C@@H](CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2=CC=CC=C12)C(O)=O

InChI Identifier

InChI=1S/C17H22N2O7/c18-10(17(24)25)5-8-6-19(11-4-2-1-3-9(8)11)16-15(23)14(22)13(21)12(7-20)26-16/h1-4,6,10,12-16,20-23H,5,7,18H2,(H,24,25)/t10-,12+,13+,14-,15+,16+/m0/s1

InChI Key

ZHBHZDMTVVJASV-JOSVURMMSA-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
Malus pumila	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-pyranosylindoles. These are nucleoside and nucleotide analogs with a structure that consists of an indole base which is N-substituted at the 1-position with a pyranose moiety. Nucleotide analogues contain a phosphate group linked to the C5 carbon atom of the pyranose.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Nucleoside and nucleotide analogues

Sub Class

1-pyranosylindoles

Direct Parent

1-pyranosylindoles

Alternative Parents

Substituents

1-pyranosylindole
Hexose monosaccharide
Indolyl carboxylic acid derivative
Glycosyl compound
N-glycosyl compound
Alpha-amino acid
Alpha-amino acid or derivatives
N-alkylindole
L-alpha-amino acid
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Benzenoid
Substituted pyrrole
Oxane
Monosaccharide
Pyrrole
Heteroaromatic compound
Secondary alcohol
Amino acid or derivatives
Amino acid
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Polyol
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Alcohol
Primary aliphatic amine
Hydrocarbon derivative
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organooxygen compound
Primary alcohol
Carbonyl group
Primary amine
Amine
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-glycosyl compound (CHEBI:76121 )
non-proteinogenic L-alpha-amino acid (CHEBI:76121 )
monosaccharide derivative (CHEBI:76121 )
L-tryptophan derivative (CHEBI:76121 )

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	-1.9	ALOGPS
logP	-3.3	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.97	ChemAxon
pKa (Strongest Basic)	9.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	158.4 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	88.76 m³·mol⁻¹	ChemAxon
Polarizability	36.96 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

9947650

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11772967

PDB ID

Not Available

ChEBI ID

76121

Good Scents ID

Not Available

References

General References

Diem S, Bergmann J, Herderich M: Tryptophan-N-glucoside in fruits and fruit juices. J Agric Food Chem. 2000 Oct;48(10):4913-7. doi: 10.1021/jf0003146. [PubMed:11052755 ]
LOTUS database [Link]

Showing NP-Card for tryptophan n-glucoside (NP0157621)

MOL for NP0157621 (tryptophan n-glucoside)

3D MOL for NP0157621 (tryptophan n-glucoside)

3D SDF for NP0157621 (tryptophan n-glucoside)

3D-SDF for NP0157621 (tryptophan n-glucoside)

PDB for NP0157621 (tryptophan n-glucoside)

3D PDB for NP0157621 (tryptophan n-glucoside)

SMILES for NP0157621 (tryptophan n-glucoside)

INCHI for NP0157621 (tryptophan n-glucoside)

Structure for NP0157621 (tryptophan n-glucoside)

3D Structure for NP0157621 (tryptophan n-glucoside)