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Showing NP-Card for Tryptophol [xylosyl-(1->6)-glucoside] (NP0049728)

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Record Information
Version2.0
Created at2022-03-17 21:17:08 UTC
Updated at2022-03-17 21:17:08 UTC
NP-MRD IDNP0049728
Secondary Accession NumbersNone
Natural Product Identification
Common NameTryptophol [xylosyl-(1->6)-glucoside]
DescriptionTryptophol [xylosyl-(1->6)-glucoside] belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Tryptophol [xylosyl-(1->6)-glucoside] is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Tryptophol [xylosyl-(1->6)-glucoside] has been detected, but not quantified in, a few different foods, such as coffee and coffee products, herbs and spices, and tea. This could make tryptophol [xylosyl-(1->6)-glucoside] a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049728 (Tryptophol [xylosyl-(1->6)-glucoside])


  Mrv0541 05061312092D          

 32 35  0  0  0  0            999 V2000
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0102   -6.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751   -4.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    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
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5623   -7.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0300   -3.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3693   -6.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8370   -3.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0919   -2.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242   -6.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5399   -1.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0722   -5.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -1.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3073   -7.8738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9213   -7.5308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3890   -3.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8989   -2.2100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4312   -5.9615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948   -0.9838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -1.3268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2652   -5.6915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3271   -4.7354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4780   -2.7246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
 10  5  1  0  0  0  0
 10  7  2  0  0  0  0
 11  3  2  0  0  0  0
 11 10  1  0  0  0  0
 12  4  2  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
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 18 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
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 23 13  1  0  0  0  0
 24 15  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 27 18  1  0  0  0  0
 28 19  1  0  0  0  0
 29  6  1  0  0  0  0
 29 21  1  0  0  0  0
 30  8  1  0  0  0  0
 30 20  1  0  0  0  0
 31  9  1  0  0  0  0
 31 20  1  0  0  0  0
 32 14  1  0  0  0  0
 32 21  1  0  0  0  0
M  END
Download

3D MOL for NP0049728 (Tryptophol [xylosyl-(1->6)-glucoside])

Download
3D SDF for NP0049728 (Tryptophol [xylosyl-(1->6)-glucoside])

  Mrv0541 05061312092D          

 32 35  0  0  0  0            999 V2000
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0102   -6.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7751   -4.1223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    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
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5623   -7.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0300   -3.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3693   -6.9177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8370   -3.1661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0919   -2.3815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6242   -6.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5399   -1.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0722   -5.5200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -1.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3073   -7.8738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9213   -7.5308    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3890   -3.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8989   -2.2100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4312   -5.9615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7948   -0.9838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -1.3268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2652   -5.6915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3271   -4.7354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4780   -2.7246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
 10  5  1  0  0  0  0
 10  7  2  0  0  0  0
 11  3  2  0  0  0  0
 11 10  1  0  0  0  0
 12  4  2  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 17 16  1  0  0  0  0
 18 15  1  0  0  0  0
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22  7  1  0  0  0  0
 22 12  1  0  0  0  0
 23 13  1  0  0  0  0
 24 15  1  0  0  0  0
 25 16  1  0  0  0  0
 26 17  1  0  0  0  0
 27 18  1  0  0  0  0
 28 19  1  0  0  0  0
 29  6  1  0  0  0  0
 29 21  1  0  0  0  0
 30  8  1  0  0  0  0
 30 20  1  0  0  0  0
 31  9  1  0  0  0  0
 31 20  1  0  0  0  0
 32 14  1  0  0  0  0
 32 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049728

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1COC(OCC2OC(OCCC3=CNC4=CC=CC=C34)C(O)C(O)C2O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C21H29NO10/c23-13-8-30-20(18(27)15(13)24)31-9-14-16(25)17(26)19(28)21(32-14)29-6-5-10-7-22-12-4-2-1-3-11(10)12/h1-4,7,13-28H,5-6,8-9H2

> <INCHI_KEY>
ONVGARFWQRCLML-UHFFFAOYSA-N

> <FORMULA>
C21H29NO10

> <MOLECULAR_WEIGHT>
455.4557

> <EXACT_MASS>
455.179146153

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
46.00444655558474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[2-(1H-indol-3-yl)ethoxy]-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.79

> <JCHEM_LOGP>
-1.3180171026666665

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.462133509497932

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.928296108179532

> <JCHEM_PKA_STRONGEST_BASIC>
-3.526580404084756

> <JCHEM_POLAR_SURFACE_AREA>
174.08999999999997

> <JCHEM_REFRACTIVITY>
107.57949999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[2-(1H-indol-3-yl)ethoxy]-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0049728 (Tryptophol [xylosyl-(1->6)-glucoside])
Download
PDB for NP0049728 (Tryptophol [xylosyl-(1->6)-glucoside])
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.680  -1.012   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.886 -12.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.314  -7.695   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.916 -13.233   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.789  -6.230   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.423 -12.913   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.296  -5.910   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.772  -4.445   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.899 -11.448   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.741  -3.301   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.868 -10.304   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.235  -3.621   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0       2.440 -14.698   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.453 -14.057   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       6.326  -7.055   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.278  -4.125   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.405 -11.128   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.217  -1.836   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.204  -2.477   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.362 -10.624   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       4.344  -8.839   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.759  -5.086   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1   11                                                       
CONECT    4    2   12                                                       
CONECT    5    6   10                                                       
CONECT    6    5   29                                                       
CONECT    7   10   22                                                       
CONECT    8   13   30                                                       
CONECT    9   14   31                                                       
CONECT   10    5    7   11                                                  
CONECT   11    3   10   12                                                  
CONECT   12    4   11   22                                                  
CONECT   13    8   15   23                                                  
CONECT   14    9   16   32                                                  
CONECT   15   13   18   24                                                  
CONECT   16   14   17   25                                                  
CONECT   17   16   19   26                                                  
CONECT   18   15   20   27                                                  
CONECT   19   17   21   28                                                  
CONECT   20   18   30   31                                                  
CONECT   21   19   29   32                                                  
CONECT   22    7   12                                                       
CONECT   23   13                                                            
CONECT   24   15                                                            
CONECT   25   16                                                            
CONECT   26   17                                                            
CONECT   27   18                                                            
CONECT   28   19                                                            
CONECT   29    6   21                                                       
CONECT   30    8   20                                                       
CONECT   31    9   20                                                       
CONECT   32   14   21                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

Download
3D PDB for NP0049728 (Tryptophol [xylosyl-(1->6)-glucoside])
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SMILES for NP0049728 (Tryptophol [xylosyl-(1->6)-glucoside])
OC1COC(OCC2OC(OCCC3=CNC4=CC=CC=C34)C(O)C(O)C2O)C(O)C1O
Download
INCHI for NP0049728 (Tryptophol [xylosyl-(1->6)-glucoside])
InChI=1S/C21H29NO10/c23-13-8-30-20(18(27)15(13)24)31-9-14-16(25)17(26)19(28)21(32-14)29-6-5-10-7-22-12-4-2-1-3-11(10)12/h1-4,7,13-28H,5-6,8-9H2
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View in JSmol
Synonyms
ValueSource
5-(3'-Benzloxy-4-methoxy)benzylbarbituric acidHMDB
Chemical FormulaC21H29NO10
Average Mass455.4557 Da
Monoisotopic Mass455.17915 Da
IUPAC Name2-[2-(1H-indol-3-yl)ethoxy]-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol
Traditional Name2-[2-(1H-indol-3-yl)ethoxy]-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol
CAS Registry Number149817-65-2
SMILES
OC1COC(OCC2OC(OCCC3=CNC4=CC=CC=C34)C(O)C(O)C2O)C(O)C1O
InChI Identifier
InChI=1S/C21H29NO10/c23-13-8-30-20(18(27)15(13)24)31-9-14-16(25)17(26)19(28)21(32-14)29-6-5-10-7-22-12-4-2-1-3-11(10)12/h1-4,7,13-28H,5-6,8-9H2
InChI KeyONVGARFWQRCLML-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Chemical Taxonomy
Description Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentO-glycosyl compounds  
Alternative Parents
Substituents
  • Disaccharide
    • 

  • O-glycosyl compound
    • 

  • 3-alkylindole
    • 

  • Indole
    • 

  • Indole or derivatives
    • 

  • Oxane
    • 

  • Benzenoid
    • 

  • Substituted pyrrole
    • 

  • Heteroaromatic compound
    • 

  • Pyrrole
    • 

  • Secondary alcohol
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Azacycle
    • 

  • Oxacycle
    • 

  • Acetal
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organopnictogen compound
    • 

  • Organic nitrogen compound
    • 

  • Alcohol
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.79ALOGPS
logP-1.3ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)11.93ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area174.09 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity107.58 m³·mol⁻¹ChemAxon
Polarizability46 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0040825  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020642  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752948  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available