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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:54 UTC

Update Date

2022-03-07 02:53:28 UTC

HMDB ID

HMDB0032801

Secondary Accession Numbers

HMDB32801

Metabolite Identification

Common Name

4-Hydroxybenzyl isothiocyanate rhamnoside

Description

4-Hydroxybenzyl isothiocyanate rhamnoside 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. 4-Hydroxybenzyl isothiocyanate rhamnoside has been detected, but not quantified in, herbs and spices. This could make 4-hydroxybenzyl isothiocyanate rhamnoside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Hydroxybenzyl isothiocyanate rhamnoside.

Structure

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

HMDB0032801
     RDKit          3D
4-Hydroxybenzyl isothiocyanate rhamnoside
 38 39  0  0  0  0  0  0  0  0999 V2000
   -4.1618    0.5067   -1.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0139    1.1598   -0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8496    0.6811   -1.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2461   -0.3421   -0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1516    0.1792    0.1821 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1662   -0.1410   -0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160   -1.0484   -0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -1.3423   -1.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9004   -0.7022   -0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3313   -1.0384   -0.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1911   -0.3073    0.3694 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5275    0.8731    0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7242    2.4738    0.0989 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4926    0.2132    0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1646    0.4718    0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1818   -1.1028    0.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4732   -2.1384    0.9945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6654   -0.1144    1.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5820   -0.7799    2.2672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2524    1.0799    0.7620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8386    2.2291    1.4353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7207    1.2037   -2.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8477    0.0192   -0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7848   -0.3001   -2.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0679    2.2569   -0.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9011   -1.0723   -1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587   -1.5846   -1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910   -2.0620   -1.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6197   -0.9103   -1.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4495   -2.1209   -0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684    0.6878    1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    1.1844    1.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0328   -1.4492   -0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1127   -2.8902    1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7982    0.2036    2.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3819   -1.7657    2.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3694    1.0258    0.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0592    3.0363    0.8758 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  2  0
  9 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20  2  1  0
 15  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 10 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
M  END


  Mrv0541 05061306422D          

 21 22  0  0  0  0            999 V2000
    0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  8  1  1  0  0  0  0
  9  2  2  0  0  0  0
  9  3  1  0  0  0  0
  9  6  1  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  8  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  6  1  0  0  0  0
 15  7  2  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19  8  1  0  0  0  0
 19 14  1  0  0  0  0
 20 10  1  0  0  0  0
 20 14  1  0  0  0  0
 21  7  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032801

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H17NO5S/c1-8-11(16)12(17)13(18)14(19-8)20-10-4-2-9(3-5-10)6-15-7-21/h2-5,8,11-14,16-18H,6H2,1H3

> <INCHI_KEY>
QAZIHHJTZPNRCM-UHFFFAOYSA-N

> <FORMULA>
C14H17NO5S

> <MOLECULAR_WEIGHT>
311.353

> <EXACT_MASS>
311.082743349

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.903795980264352

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[4-(isothiocyanatomethyl)phenoxy]-6-methyloxane-3,4,5-triol

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.2693997230000005

> <ALOGPS_LOGS>
-2.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.268673179562938

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.213623015327396

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6122003585840474

> <JCHEM_POLAR_SURFACE_AREA>
91.51000000000002

> <JCHEM_REFRACTIVITY>
78.52330000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[4-(isothiocyanatomethyl)phenoxy]-6-methyloxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032801
     RDKit          3D
4-Hydroxybenzyl isothiocyanate rhamnoside
 38 39  0  0  0  0  0  0  0  0999 V2000
   -4.1618    0.5067   -1.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0139    1.1598   -0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8496    0.6811   -1.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2461   -0.3421   -0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1516    0.1792    0.1821 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1662   -0.1410   -0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160   -1.0484   -0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -1.3423   -1.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9004   -0.7022   -0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3313   -1.0384   -0.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1911   -0.3073    0.3694 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5275    0.8731    0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7242    2.4738    0.0989 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4926    0.2132    0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1646    0.4718    0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1818   -1.1028    0.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4732   -2.1384    0.9945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6654   -0.1144    1.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5820   -0.7799    2.2672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2524    1.0799    0.7620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8386    2.2291    1.4353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7207    1.2037   -2.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8477    0.0192   -0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7848   -0.3001   -2.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0679    2.2569   -0.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9011   -1.0723   -1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587   -1.5846   -1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910   -2.0620   -1.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6197   -0.9103   -1.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4495   -2.1209   -0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684    0.6878    1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    1.1844    1.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0328   -1.4492   -0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1127   -2.8902    1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7982    0.2036    2.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3819   -1.7657    2.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3694    1.0258    0.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0592    3.0363    0.8758 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  2  0
  9 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20  2  1  0
 15  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 10 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
M  END

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       1.334  13.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       5.335   1.540   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667  10.780   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
HETATM   21  S   UNK     0       5.335  -1.540   0.000  0.00  0.00           S+0
CONECT    1    8                                                            
CONECT    2    4    9                                                       
CONECT    3    5    9                                                       
CONECT    4    2   10                                                       
CONECT    5    3   10                                                       
CONECT    6    9   15                                                       
CONECT    7   15   21                                                       
CONECT    8    1   11   19                                                  
CONECT    9    2    3    6                                                  
CONECT   10    4    5   20                                                  
CONECT   11    8   12   16                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   19   20                                                  
CONECT   15    6    7                                                       
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19    8   14                                                       
CONECT   20   10   14                                                       
CONECT   21    7                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0032801
HETATM    1  C1  UNL     1      -4.162   0.507  -1.450  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.014   1.160  -0.702  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.850   0.681  -1.179  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.246  -0.342  -0.502  1.00  0.00           C  
HETATM    5  O2  UNL     1      -0.152   0.179   0.182  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.166  -0.141  -0.015  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.616  -1.048  -0.942  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.975  -1.342  -1.106  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.900  -0.702  -0.314  1.00  0.00           C  
HETATM   10  C8  UNL     1       5.331  -1.038  -0.515  1.00  0.00           C  
HETATM   11  N1  UNL     1       6.191  -0.307   0.369  1.00  0.00           N  
HETATM   12  C9  UNL     1       6.527   0.873   0.042  1.00  0.00           C  
HETATM   13  S1  UNL     1       6.724   2.474   0.099  1.00  0.00           S  
HETATM   14  C10 UNL     1       3.493   0.213   0.626  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.165   0.472   0.756  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.182  -1.103   0.409  1.00  0.00           C  
HETATM   17  O3  UNL     1      -1.473  -2.138   0.995  1.00  0.00           O  
HETATM   18  C13 UNL     1      -2.665  -0.114   1.444  1.00  0.00           C  
HETATM   19  O4  UNL     1      -3.582  -0.780   2.267  1.00  0.00           O  
HETATM   20  C14 UNL     1      -3.252   1.080   0.762  1.00  0.00           C  
HETATM   21  O5  UNL     1      -2.839   2.229   1.435  1.00  0.00           O  
HETATM   22  H1  UNL     1      -4.721   1.204  -2.088  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.848   0.019  -0.728  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.785  -0.300  -2.140  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.068   2.257  -0.978  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.901  -1.072  -1.252  1.00  0.00           H  
HETATM   27  H6  UNL     1       0.959  -1.585  -1.593  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.291  -2.062  -1.846  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.620  -0.910  -1.596  1.00  0.00           H  
HETATM   30  H9  UNL     1       5.450  -2.121  -0.294  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.268   0.688   1.224  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.816   1.184   1.484  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.033  -1.449  -0.172  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.113  -2.890   1.143  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.798   0.204   2.071  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.382  -1.766   2.300  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.369   1.026   0.927  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.059   3.036   0.876  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   20   25
CONECT    3    4
CONECT    4    5   16   26
CONECT    5    6
CONECT    6    7    7   15
CONECT    7    8   27
CONECT    8    9    9   28
CONECT    9   10   14
CONECT   10   11   29   30
CONECT   11   12   12
CONECT   12   13   13
CONECT   14   15   15   31
CONECT   15   32
CONECT   16   17   18   33
CONECT   17   34
CONECT   18   19   20   35
CONECT   19   36
CONECT   20   21   37
CONECT   21   38
END

HMDB0032801
     RDKit          3D
4-Hydroxybenzyl isothiocyanate rhamnoside
 38 39  0  0  0  0  0  0  0  0999 V2000
   -4.1618    0.5067   -1.4495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0139    1.1598   -0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8496    0.6811   -1.1787 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2461   -0.3421   -0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1516    0.1792    0.1821 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1662   -0.1410   -0.0153 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6160   -1.0484   -0.9420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -1.3423   -1.1063 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9004   -0.7022   -0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3313   -1.0384   -0.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1911   -0.3073    0.3694 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5275    0.8731    0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7242    2.4738    0.0989 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4926    0.2132    0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1646    0.4718    0.7562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1818   -1.1028    0.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4732   -2.1384    0.9945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6654   -0.1144    1.4437 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5820   -0.7799    2.2672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2524    1.0799    0.7620 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8386    2.2291    1.4353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7207    1.2037   -2.0882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8477    0.0192   -0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7848   -0.3001   -2.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0679    2.2569   -0.9784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9011   -1.0723   -1.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9587   -1.5846   -1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2910   -2.0620   -1.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6197   -0.9103   -1.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4495   -2.1209   -0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684    0.6878    1.2242 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8163    1.1844    1.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0328   -1.4492   -0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1127   -2.8902    1.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7982    0.2036    2.0712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3819   -1.7657    2.2998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3694    1.0258    0.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0592    3.0363    0.8758 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  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  2  0
  9 14  1  0
 14 15  2  0
  4 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20  2  1  0
 15  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  4 26  1  0
  7 27  1  0
  8 28  1  0
 10 29  1  0
 10 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
 20 37  1  0
 21 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxybenzyl isothiocyanic acid rhamnoside	Generator
Moringin	MeSH

Chemical Formula

C₁₄H₁₇NO₅S

Average Molecular Weight

311.353

Monoisotopic Molecular Weight

311.082743349

IUPAC Name

2-[4-(isothiocyanatomethyl)phenoxy]-6-methyloxane-3,4,5-triol

Traditional Name

2-[4-(isothiocyanatomethyl)phenoxy]-6-methyloxane-3,4,5-triol

CAS Registry Number

73255-40-0

SMILES

CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C14H17NO5S/c1-8-11(16)12(17)13(18)14(19-8)20-10-4-2-9(3-5-10)6-15-7-21/h2-5,8,11-14,16-18H,6H2,1H3

InChI Key

QAZIHHJTZPNRCM-UHFFFAOYSA-N

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
O-glycosyl compound
Phenoxy compound
Phenol ether
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Isothiocyanate
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Alcohol
Organonitrogen compound
Organosulfur compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032801)
Cytoplasm (HMDB: HMDB0032801)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032801)

Source

Exogenous

Exogenous (HMDB: HMDB0032801)

Food

Food (HMDB: HMDB0032801)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0032801)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032801)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	74 °C	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
Water Solubility	0.64 g/L	ALOGPS
logP	1.42	ALOGPS
logP	1.27	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	91.51 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.52 m³·mol⁻¹	ChemAxon
Polarizability	31.9 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
DarkChem	[M+H]+	172.756	31661259
DarkChem	[M-H]-	166.568	31661259
DeepCCS	[M+H]+	166.181	30932474
DeepCCS	[M-H]-	163.823	30932474
DeepCCS	[M-2H]-	196.864	30932474
DeepCCS	[M+Na]+	172.274	30932474
AllCCS	[M+H]+	172.4	32859911
AllCCS	[M+H-H2O]+	169.3	32859911
AllCCS	[M+NH4]+	175.4	32859911
AllCCS	[M+Na]+	176.2	32859911
AllCCS	[M-H]-	170.9	32859911
AllCCS	[M+Na-2H]-	171.1	32859911
AllCCS	[M+HCOO]-	171.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.72 minutes	32390414
Predicted by Siyang on May 30, 2022	10.0634 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.54 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	73.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1543.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	225.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	113.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	61.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	325.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	394.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	120.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	722.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	362.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1048.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	236.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	248.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	352.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	218.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	83.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxybenzyl isothiocyanate rhamnoside	CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O)C(O)C1O	4440.7	Standard polar	33892256
4-Hydroxybenzyl isothiocyanate rhamnoside	CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O)C(O)C1O	2740.1	Standard non polar	33892256
4-Hydroxybenzyl isothiocyanate rhamnoside	CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O)C(O)C1O	2808.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxybenzyl isothiocyanate rhamnoside,1TMS,isomer #1	CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O[Si](C)(C)C)C(O)C1O	2618.4	Semi standard non polar	33892256
4-Hydroxybenzyl isothiocyanate rhamnoside,1TMS,isomer #2	CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O)C(O[Si](C)(C)C)C1O	2638.9	Semi standard non polar	33892256
4-Hydroxybenzyl isothiocyanate rhamnoside,1TMS,isomer #3	CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O)C(O)C1O[Si](C)(C)C	2657.8	Semi standard non polar	33892256
4-Hydroxybenzyl isothiocyanate rhamnoside,2TMS,isomer #1	CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O	2610.9	Semi standard non polar	33892256
4-Hydroxybenzyl isothiocyanate rhamnoside,2TMS,isomer #2	CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C	2623.9	Semi standard non polar	33892256
4-Hydroxybenzyl isothiocyanate rhamnoside,2TMS,isomer #3	CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2638.1	Semi standard non polar	33892256
4-Hydroxybenzyl isothiocyanate rhamnoside,3TMS,isomer #1	CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	2633.4	Semi standard non polar	33892256
4-Hydroxybenzyl isothiocyanate rhamnoside,1TBDMS,isomer #1	CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	2895.9	Semi standard non polar	33892256
4-Hydroxybenzyl isothiocyanate rhamnoside,1TBDMS,isomer #2	CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O)C(O[Si](C)(C)C(C)(C)C)C1O	2906.0	Semi standard non polar	33892256
4-Hydroxybenzyl isothiocyanate rhamnoside,1TBDMS,isomer #3	CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O)C(O)C1O[Si](C)(C)C(C)(C)C	2922.3	Semi standard non polar	33892256
4-Hydroxybenzyl isothiocyanate rhamnoside,2TBDMS,isomer #1	CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	3097.7	Semi standard non polar	33892256
4-Hydroxybenzyl isothiocyanate rhamnoside,2TBDMS,isomer #2	CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	3105.4	Semi standard non polar	33892256
4-Hydroxybenzyl isothiocyanate rhamnoside,2TBDMS,isomer #3	CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3109.2	Semi standard non polar	33892256
4-Hydroxybenzyl isothiocyanate rhamnoside,3TBDMS,isomer #1	CC1OC(OC2=CC=C(CN=C=S)C=C2)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	3273.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxybenzyl isothiocyanate rhamnoside GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4u-9640000000-6207d6b31a0ee31657b8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxybenzyl isothiocyanate rhamnoside GC-MS (3 TMS) - 70eV, Positive	splash10-03di-3942370000-1fe633044ead93f36592	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxybenzyl isothiocyanate rhamnoside GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzyl isothiocyanate rhamnoside 10V, Positive-QTOF	splash10-02t9-0943000000-603d5b6571df56befc88	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzyl isothiocyanate rhamnoside 20V, Positive-QTOF	splash10-0aor-0910000000-13def0973881f675eeed	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzyl isothiocyanate rhamnoside 40V, Positive-QTOF	splash10-0a4i-2900000000-d8a303bca8fe9df2b797	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzyl isothiocyanate rhamnoside 10V, Negative-QTOF	splash10-03di-6849000000-f12dbc47dda4fff75160	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzyl isothiocyanate rhamnoside 20V, Negative-QTOF	splash10-03di-4910000000-d94bb095929fc3374520	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzyl isothiocyanate rhamnoside 40V, Negative-QTOF	splash10-0a4i-9400000000-44b7fb511350b287577b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzyl isothiocyanate rhamnoside 10V, Positive-QTOF	splash10-0aor-0900000000-a3b39a66900c60f23b3a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzyl isothiocyanate rhamnoside 20V, Positive-QTOF	splash10-0a4i-2920000000-84f6983c581ab244846a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzyl isothiocyanate rhamnoside 40V, Positive-QTOF	splash10-0a59-4900000000-6242a128c744e8923f3c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzyl isothiocyanate rhamnoside 10V, Negative-QTOF	splash10-0a4i-9000000000-286b63d3516de7d14a12	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzyl isothiocyanate rhamnoside 20V, Negative-QTOF	splash10-0a4i-9000000000-286b63d3516de7d14a12	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzyl isothiocyanate rhamnoside 40V, Negative-QTOF	splash10-0a4i-9000000000-fb6e848ddb6fb376541c	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB010773

KNApSAcK ID

Not Available

Chemspider ID

11590012

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14865502

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 4-Hydroxybenzyl isothiocyanate rhamnoside (HMDB0032801)

MOL for HMDB0032801 (4-Hydroxybenzyl isothiocyanate rhamnoside)

3D MOL for HMDB0032801 (4-Hydroxybenzyl isothiocyanate rhamnoside)

3D SDF for HMDB0032801 (4-Hydroxybenzyl isothiocyanate rhamnoside)

3D-SDF for HMDB0032801 (4-Hydroxybenzyl isothiocyanate rhamnoside)

PDB for HMDB0032801 (4-Hydroxybenzyl isothiocyanate rhamnoside)

3D PDB for HMDB0032801 (4-Hydroxybenzyl isothiocyanate rhamnoside)

SMILES for HMDB0032801 (4-Hydroxybenzyl isothiocyanate rhamnoside)

INCHI for HMDB0032801 (4-Hydroxybenzyl isothiocyanate rhamnoside)

Structure for HMDB0032801 (4-Hydroxybenzyl isothiocyanate rhamnoside)

3D Structure for HMDB0032801 (4-Hydroxybenzyl isothiocyanate rhamnoside)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra