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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:51:16 UTC

Update Date

2022-03-07 02:53:58 UTC

HMDB ID

HMDB0034070

Secondary Accession Numbers

HMDB34070

Metabolite Identification

Common Name

Sinigrin

Description

Sinigrin belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain. Sinigrin is a bitter tasting compound. Sinigrin is found, on average, in the highest concentration within brussel sprouts (Brassica oleracea var. gemmifera) and cauliflowers (Brassica oleracea var. botrytis). Sinigrin has also been detected, but not quantified in, several different foods, such as radishes (Raphanus sativus), common cabbages (Brassica oleracea), cabbages (Brassica oleracea var. capitata), wasabis (Wasabia japonica), and white cabbages (Brassica oleracea L. var. capitata L. f. alba DC.). This could make sinigrin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Sinigrin.

Structure

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

HMDB0034070
     RDKit          3D
Sinigrin
 39 39  0  0  0  0  0  0  0  0999 V2000
    3.6790    2.9131    1.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6776    1.7817    1.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.7846   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614    0.8363   -0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0194   -0.1271   -1.0210 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1142   -0.2255   -1.8164 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115   -1.6381   -2.5959 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.0137   -1.9397   -2.1325 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600   -1.5300   -4.0788 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6247   -2.9505   -2.1646 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5630    1.0621    0.9340 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6452   -0.2478    0.5867 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1623   -0.0958   -0.6461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858   -0.1261   -0.8667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9993    1.3134   -0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3450    1.9713   -2.0122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3226   -0.9590    0.0425 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8696   -2.0713   -0.5962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6101   -1.4449    1.2719 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5229   -1.7928    2.2563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6603   -0.3702    1.6981 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9565   -0.7068    2.8581 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2570    3.8164    1.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145    2.8949    2.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0932    0.8635    1.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7315    2.8020   -0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9091    1.5373   -0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0130   -3.3146   -1.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0821   -1.2290    0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6545   -0.5336   -1.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171    1.8705   -0.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0828    1.3112   -1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0616    2.4800   -2.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1777   -0.3372    0.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9115   -1.9469   -1.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0205   -2.3437    0.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0975   -2.3393    2.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2091    0.5654    1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4279   -1.5336    2.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
  4 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 12  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
 10 28  1  0
 12 29  1  6
 14 30  1  6
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  1
 18 35  1  0
 19 36  1  6
 20 37  1  0
 21 38  1  1
 22 39  1  0
M  END


  Mrv0541 02241215142D          

 22 22  0  0  1  0            999 V2000
   -1.3415   -1.2457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6270   -0.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875   -1.2457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8019   -0.8332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5164   -1.2457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2309   -0.8332    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3743   -1.2457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0888   -0.8332    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8032   -0.4207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5013   -1.5477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6763   -0.1187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5164   -2.0707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2309   -2.4832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8019   -2.4832    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8019   -3.3082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0875   -2.0707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6270   -2.4832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9454   -1.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9454   -2.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6598   -2.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6598   -3.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6598   -0.8332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
  8 11  2  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  6  0  0  0
  6 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 18 22  2  0  0  0  0
 22  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034070

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@H]1O[C@@H](S\C(=N\OS(O)(=O)=O)CC=C)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H17NO9S2/c1-2-3-6(11-20-22(16,17)18)21-10-9(15)8(14)7(13)5(4-12)19-10/h2,5,7-10,12-15H,1,3-4H2,(H,16,17,18)/b11-6+/t5-,7-,8+,9-,10+/m1/s1

> <INCHI_KEY>
PHZOWSSBXJXFOR-PTGZALFTSA-N

> <FORMULA>
C10H17NO9S2

> <MOLECULAR_WEIGHT>
359.373

> <EXACT_MASS>
359.034472527

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
32.48707473812115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(E)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxy}sulfonic acid

> <ALOGPS_LOGP>
-1.73

> <JCHEM_LOGP>
-3.2342296417139957

> <ALOGPS_LOGS>
-1.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.447214216566284

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.6183476179623524

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4916051886020759

> <JCHEM_POLAR_SURFACE_AREA>
166.11

> <JCHEM_REFRACTIVITY>
74.69709999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.26e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(E)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxysulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034070
     RDKit          3D
Sinigrin
 39 39  0  0  0  0  0  0  0  0999 V2000
    3.6790    2.9131    1.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6776    1.7817    1.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.7846   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614    0.8363   -0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0194   -0.1271   -1.0210 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1142   -0.2255   -1.8164 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115   -1.6381   -2.5959 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.0137   -1.9397   -2.1325 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600   -1.5300   -4.0788 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6247   -2.9505   -2.1646 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5630    1.0621    0.9340 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6452   -0.2478    0.5867 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1623   -0.0958   -0.6461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858   -0.1261   -0.8667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9993    1.3134   -0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3450    1.9713   -2.0122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3226   -0.9590    0.0425 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8696   -2.0713   -0.5962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6101   -1.4449    1.2719 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5229   -1.7928    2.2563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6603   -0.3702    1.6981 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9565   -0.7068    2.8581 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2570    3.8164    1.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145    2.8949    2.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0932    0.8635    1.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7315    2.8020   -0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9091    1.5373   -0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0130   -3.3146   -1.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0821   -1.2290    0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6545   -0.5336   -1.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171    1.8705   -0.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0828    1.3112   -1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0616    2.4800   -2.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1777   -0.3372    0.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9115   -1.9469   -1.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0205   -2.3437    0.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0975   -2.3393    2.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2091    0.5654    1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4279   -1.5336    2.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
  4 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 12  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
 10 28  1  0
 12 29  1  6
 14 30  1  6
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  1
 18 35  1  0
 19 36  1  6
 20 37  1  0
 21 38  1  1
 22 39  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -2.504  -2.325   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.170  -1.555   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.163  -2.325   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.497  -1.555   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.831  -2.325   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0       4.164  -1.555   0.000  0.00  0.00           S+0
HETATM    7  O   UNK     0       8.165  -2.325   0.000  0.00  0.00           O+0
HETATM    8  S   UNK     0       9.499  -1.555   0.000  0.00  0.00           S+0
HETATM    9  O   UNK     0      10.833  -0.785   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      10.269  -2.889   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       8.729  -0.222   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.831  -3.865   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.164  -4.635   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.497  -4.635   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.497  -6.175   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.163  -3.865   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.170  -4.635   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.498  -2.325   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.498  -3.865   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.832  -4.635   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.832  -6.175   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       6.832  -1.555   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5   18                                                       
CONECT    7    8   22                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
CONECT   12    5   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    3   17                                                  
CONECT   17   16                                                            
CONECT   18    6   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   18    7                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0034070
HETATM    1  C1  UNL     1       3.679   2.913   1.986  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.678   1.782   1.286  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.079   1.785  -0.095  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.961   0.836  -0.170  1.00  0.00           C  
HETATM    5  N1  UNL     1       2.019  -0.127  -1.021  1.00  0.00           N  
HETATM    6  O1  UNL     1       3.114  -0.226  -1.816  1.00  0.00           O  
HETATM    7  S1  UNL     1       3.612  -1.638  -2.596  1.00  0.00           S  
HETATM    8  O2  UNL     1       5.014  -1.940  -2.133  1.00  0.00           O  
HETATM    9  O3  UNL     1       3.560  -1.530  -4.079  1.00  0.00           O  
HETATM   10  O4  UNL     1       2.625  -2.950  -2.165  1.00  0.00           O  
HETATM   11  S2  UNL     1       0.563   1.062   0.934  1.00  0.00           S  
HETATM   12  C5  UNL     1      -0.645  -0.248   0.587  1.00  0.00           C  
HETATM   13  O5  UNL     1      -1.162  -0.096  -0.646  1.00  0.00           O  
HETATM   14  C6  UNL     1      -2.486  -0.126  -0.867  1.00  0.00           C  
HETATM   15  C7  UNL     1      -2.999   1.313  -0.949  1.00  0.00           C  
HETATM   16  O6  UNL     1      -2.345   1.971  -2.012  1.00  0.00           O  
HETATM   17  C8  UNL     1      -3.323  -0.959   0.043  1.00  0.00           C  
HETATM   18  O7  UNL     1      -3.870  -2.071  -0.596  1.00  0.00           O  
HETATM   19  C9  UNL     1      -2.610  -1.445   1.272  1.00  0.00           C  
HETATM   20  O8  UNL     1      -3.523  -1.793   2.256  1.00  0.00           O  
HETATM   21  C10 UNL     1      -1.660  -0.370   1.698  1.00  0.00           C  
HETATM   22  O9  UNL     1      -0.957  -0.707   2.858  1.00  0.00           O  
HETATM   23  H1  UNL     1       3.257   3.816   1.565  1.00  0.00           H  
HETATM   24  H2  UNL     1       4.114   2.895   2.984  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.093   0.863   1.685  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.732   2.802  -0.347  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.909   1.537  -0.785  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.013  -3.315  -1.325  1.00  0.00           H  
HETATM   29  H7  UNL     1      -0.082  -1.229   0.600  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.654  -0.534  -1.910  1.00  0.00           H  
HETATM   31  H9  UNL     1      -2.717   1.870  -0.035  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.083   1.311  -1.077  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.062   2.480  -2.496  1.00  0.00           H  
HETATM   34  H12 UNL     1      -4.178  -0.337   0.384  1.00  0.00           H  
HETATM   35  H13 UNL     1      -3.911  -1.947  -1.579  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.021  -2.344   0.999  1.00  0.00           H  
HETATM   37  H15 UNL     1      -3.098  -2.339   2.936  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.209   0.565   1.906  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.428  -1.534   2.720  1.00  0.00           H  
CONECT    1    2    2   23   24
CONECT    2    3   25
CONECT    3    4   26   27
CONECT    4    5    5   11
CONECT    5    6
CONECT    6    7
CONECT    7    8    8    9    9
CONECT    7   10
CONECT   10   28
CONECT   11   12
CONECT   12   13   21   29
CONECT   13   14
CONECT   14   15   17   30
CONECT   15   16   31   32
CONECT   16   33
CONECT   17   18   19   34
CONECT   18   35
CONECT   19   20   21   36
CONECT   20   37
CONECT   21   22   38
CONECT   22   39
END

HMDB0034070
     RDKit          3D
Sinigrin
 39 39  0  0  0  0  0  0  0  0999 V2000
    3.6790    2.9131    1.9856 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6776    1.7817    1.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.7846   -0.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9614    0.8363   -0.1695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0194   -0.1271   -1.0210 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1142   -0.2255   -1.8164 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6115   -1.6381   -2.5959 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.0137   -1.9397   -2.1325 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5600   -1.5300   -4.0788 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6247   -2.9505   -2.1646 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5630    1.0621    0.9340 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6452   -0.2478    0.5867 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1623   -0.0958   -0.6461 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4858   -0.1261   -0.8667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9993    1.3134   -0.9493 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3450    1.9713   -2.0122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3226   -0.9590    0.0425 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8696   -2.0713   -0.5962 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6101   -1.4449    1.2719 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5229   -1.7928    2.2563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6603   -0.3702    1.6981 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9565   -0.7068    2.8581 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2570    3.8164    1.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145    2.8949    2.9842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0932    0.8635    1.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7315    2.8020   -0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9091    1.5373   -0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0130   -3.3146   -1.3252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0821   -1.2290    0.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6545   -0.5336   -1.9100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171    1.8705   -0.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0828    1.3112   -1.0775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0616    2.4800   -2.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1777   -0.3372    0.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9115   -1.9469   -1.5786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0205   -2.3437    0.9987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0975   -2.3393    2.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2091    0.5654    1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4279   -1.5336    2.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  2  0
  7 10  1  0
  4 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 12  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
 10 28  1  0
 12 29  1  6
 14 30  1  6
 15 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  1
 18 35  1  0
 19 36  1  6
 20 37  1  0
 21 38  1  1
 22 39  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-thio-b-D-Glucopyranose 1-[N-(sulfooxy)-3-butenimidate], 9ci	HMDB
2-Phenylethyl glucosinolate	HMDB
Allyl glucosinolate	HMDB
Myronate	HMDB
Myronic acid	HMDB
Sinigrin, monopotassium salt	MeSH, HMDB
{[(e)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxy}sulfonate	Generator
{[(e)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}but-3-en-1-ylidene)amino]oxy}sulphonate	Generator
{[(e)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulphanyl}but-3-en-1-ylidene)amino]oxy}sulphonic acid	Generator
Sinigrin	MeSH

Chemical Formula

C₁₀H₁₇NO₉S₂

Average Molecular Weight

359.373

Monoisotopic Molecular Weight

359.034472527

IUPAC Name

{[(E)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxy}sulfonic acid

Traditional Name

[(E)-(1-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl}but-3-en-1-ylidene)amino]oxysulfonic acid

CAS Registry Number

534-69-0

SMILES

OC[C@H]1O[C@@H](S\C(=N\OS(O)(=O)=O)CC=C)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C10H17NO9S2/c1-2-3-6(11-20-22(16,17)18)21-10-9(15)8(14)7(13)5(4-12)19-10/h2,5,7-10,12-15H,1,3-4H2,(H,16,17,18)/b11-6+/t5-,7-,8+,9-,10+/m1/s1

InChI Key

PHZOWSSBXJXFOR-PTGZALFTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkylglucosinolates. These are organic compounds containing a glucosinolate moiety that carries an alkyl chain.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Alkylglucosinolates

Alternative Parents

Substituents

Alkylglucosinolate
Glycosyl compound
S-glycosyl compound
Oxane
Monothioacetal
Organic sulfuric acid or derivatives
Secondary alcohol
Polyol
Oxacycle
Organoheterocyclic compound
Sulfenyl compound
Alcohol
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Organic oxide
Primary alcohol
Organic nitrogen compound
Organopnictogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	125 - 127 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.049 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	22.6 g/L	ALOGPS
logP	-1.7	ALOGPS
logP	-3.2	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	-3.6	ChemAxon
pKa (Strongest Basic)	-0.49	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	166.11 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	74.7 m³·mol⁻¹	ChemAxon
Polarizability	32.49 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	172.962	30932474
DeepCCS	[M-H]-	170.604	30932474
DeepCCS	[M-2H]-	204.161	30932474
DeepCCS	[M+Na]+	179.578	30932474
AllCCS	[M+H]+	177.6	32859911
AllCCS	[M+H-H2O]+	174.9	32859911
AllCCS	[M+NH4]+	180.1	32859911
AllCCS	[M+Na]+	180.8	32859911
AllCCS	[M-H]-	170.2	32859911
AllCCS	[M+Na-2H]-	170.5	32859911
AllCCS	[M+HCOO]-	170.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sinigrin	OC[C@H]1O[C@@H](S\C(=N\OS(O)(=O)=O)CC=C)[C@H](O)[C@@H](O)[C@@H]1O	4435.4	Standard polar	33892256
Sinigrin	OC[C@H]1O[C@@H](S\C(=N\OS(O)(=O)=O)CC=C)[C@H](O)[C@@H](O)[C@@H]1O	2295.4	Standard non polar	33892256
Sinigrin	OC[C@H]1O[C@@H](S\C(=N\OS(O)(=O)=O)CC=C)[C@H](O)[C@@H](O)[C@@H]1O	2862.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sinigrin,1TMS,isomer #1	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	2710.2	Semi standard non polar	33892256
Sinigrin,1TMS,isomer #2	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	2713.4	Semi standard non polar	33892256
Sinigrin,1TMS,isomer #3	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	2725.3	Semi standard non polar	33892256
Sinigrin,1TMS,isomer #4	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	2699.7	Semi standard non polar	33892256
Sinigrin,1TMS,isomer #5	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C)S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O	2767.5	Semi standard non polar	33892256
Sinigrin,2TMS,isomer #1	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	2626.0	Semi standard non polar	33892256
Sinigrin,2TMS,isomer #10	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C)S[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	2654.4	Semi standard non polar	33892256
Sinigrin,2TMS,isomer #2	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	2634.4	Semi standard non polar	33892256
Sinigrin,2TMS,isomer #3	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	2640.0	Semi standard non polar	33892256
Sinigrin,2TMS,isomer #4	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C)S[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	2674.1	Semi standard non polar	33892256
Sinigrin,2TMS,isomer #5	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	2628.6	Semi standard non polar	33892256
Sinigrin,2TMS,isomer #6	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2663.4	Semi standard non polar	33892256
Sinigrin,2TMS,isomer #7	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C)S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	2674.8	Semi standard non polar	33892256
Sinigrin,2TMS,isomer #8	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	2650.9	Semi standard non polar	33892256
Sinigrin,2TMS,isomer #9	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C)S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	2675.5	Semi standard non polar	33892256
Sinigrin,3TMS,isomer #1	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	2606.0	Semi standard non polar	33892256
Sinigrin,3TMS,isomer #10	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C)S[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	2619.1	Semi standard non polar	33892256
Sinigrin,3TMS,isomer #2	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	2597.6	Semi standard non polar	33892256
Sinigrin,3TMS,isomer #3	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C)S[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	2606.2	Semi standard non polar	33892256
Sinigrin,3TMS,isomer #4	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2610.2	Semi standard non polar	33892256
Sinigrin,3TMS,isomer #5	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C)S[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	2618.0	Semi standard non polar	33892256
Sinigrin,3TMS,isomer #6	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C)S[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	2612.1	Semi standard non polar	33892256
Sinigrin,3TMS,isomer #7	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2620.1	Semi standard non polar	33892256
Sinigrin,3TMS,isomer #8	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C)S[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	2607.8	Semi standard non polar	33892256
Sinigrin,3TMS,isomer #9	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C)S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2633.5	Semi standard non polar	33892256
Sinigrin,4TMS,isomer #1	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2604.0	Semi standard non polar	33892256
Sinigrin,4TMS,isomer #2	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C)S[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	2610.3	Semi standard non polar	33892256
Sinigrin,4TMS,isomer #3	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C)S[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	2597.5	Semi standard non polar	33892256
Sinigrin,4TMS,isomer #4	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C)S[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2616.3	Semi standard non polar	33892256
Sinigrin,4TMS,isomer #5	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C)S[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2611.0	Semi standard non polar	33892256
Sinigrin,5TMS,isomer #1	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C)S[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2613.1	Semi standard non polar	33892256
Sinigrin,5TMS,isomer #1	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C)S[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3177.5	Standard non polar	33892256
Sinigrin,1TBDMS,isomer #1	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	2947.8	Semi standard non polar	33892256
Sinigrin,1TBDMS,isomer #2	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2931.5	Semi standard non polar	33892256
Sinigrin,1TBDMS,isomer #3	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2939.7	Semi standard non polar	33892256
Sinigrin,1TBDMS,isomer #4	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	2917.2	Semi standard non polar	33892256
Sinigrin,1TBDMS,isomer #5	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C(C)(C)C)S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O	2993.9	Semi standard non polar	33892256
Sinigrin,2TBDMS,isomer #1	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	3057.9	Semi standard non polar	33892256
Sinigrin,2TBDMS,isomer #10	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C(C)(C)C)S[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	3083.1	Semi standard non polar	33892256
Sinigrin,2TBDMS,isomer #2	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3075.0	Semi standard non polar	33892256
Sinigrin,2TBDMS,isomer #3	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3079.5	Semi standard non polar	33892256
Sinigrin,2TBDMS,isomer #4	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C(C)(C)C)S[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	3114.9	Semi standard non polar	33892256
Sinigrin,2TBDMS,isomer #5	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3051.3	Semi standard non polar	33892256
Sinigrin,2TBDMS,isomer #6	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3072.0	Semi standard non polar	33892256
Sinigrin,2TBDMS,isomer #7	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C(C)(C)C)S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3111.8	Semi standard non polar	33892256
Sinigrin,2TBDMS,isomer #8	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3059.9	Semi standard non polar	33892256
Sinigrin,2TBDMS,isomer #9	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C(C)(C)C)S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3114.3	Semi standard non polar	33892256
Sinigrin,3TBDMS,isomer #1	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3206.3	Semi standard non polar	33892256
Sinigrin,3TBDMS,isomer #10	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C(C)(C)C)S[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3203.4	Semi standard non polar	33892256
Sinigrin,3TBDMS,isomer #2	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3183.2	Semi standard non polar	33892256
Sinigrin,3TBDMS,isomer #3	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C(C)(C)C)S[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	3225.6	Semi standard non polar	33892256
Sinigrin,3TBDMS,isomer #4	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3207.6	Semi standard non polar	33892256
Sinigrin,3TBDMS,isomer #5	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C(C)(C)C)S[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3233.0	Semi standard non polar	33892256
Sinigrin,3TBDMS,isomer #6	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C(C)(C)C)S[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3250.6	Semi standard non polar	33892256
Sinigrin,3TBDMS,isomer #7	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3192.7	Semi standard non polar	33892256
Sinigrin,3TBDMS,isomer #8	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C(C)(C)C)S[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3209.9	Semi standard non polar	33892256
Sinigrin,3TBDMS,isomer #9	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C(C)(C)C)S[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3231.5	Semi standard non polar	33892256
Sinigrin,4TBDMS,isomer #1	C=CC/C(=N\OS(=O)(=O)O)S[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3351.7	Semi standard non polar	33892256
Sinigrin,4TBDMS,isomer #2	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C(C)(C)C)S[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	3381.4	Semi standard non polar	33892256
Sinigrin,4TBDMS,isomer #3	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C(C)(C)C)S[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	3374.0	Semi standard non polar	33892256
Sinigrin,4TBDMS,isomer #4	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C(C)(C)C)S[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3392.8	Semi standard non polar	33892256
Sinigrin,4TBDMS,isomer #5	C=CC/C(=N\OS(=O)(=O)O[Si](C)(C)C(C)(C)C)S[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	3365.1	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 - Sinigrin GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9423000000-7647c2c4ab14297fbb5c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sinigrin GC-MS (4 TMS) - 70eV, Positive	splash10-001i-5212139000-44f0f7f5b1e1360d77d3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sinigrin 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 - Sinigrin 10V, Positive-QTOF	splash10-01ow-2917000000-1e5e9dddb7150c7f6ba9	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinigrin 20V, Positive-QTOF	splash10-0gxt-6980000000-b9e4cac65ffb45350417	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinigrin 40V, Positive-QTOF	splash10-0006-9100000000-8e04e4b3fd539b9910cd	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinigrin 10V, Negative-QTOF	splash10-0002-3910000000-82262583417df5e92578	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinigrin 20V, Negative-QTOF	splash10-03di-8900000000-c5ab479eb8b63e48f693	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinigrin 40V, Negative-QTOF	splash10-03k9-5900000000-6402ab08001a62f077de	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinigrin 10V, Positive-QTOF	splash10-03di-0009000000-25d4cebfa4dd0d0d7c6a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinigrin 20V, Positive-QTOF	splash10-0ikc-2595000000-e11c08f1fe56eef4efef	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinigrin 40V, Positive-QTOF	splash10-0gi0-9720000000-9e0bb14e5e2fa4101e43	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinigrin 10V, Negative-QTOF	splash10-0bta-0908000000-b7abdde860347283b8af	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinigrin 20V, Negative-QTOF	splash10-06s2-4912000000-1e889da8b56a1c237bc5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sinigrin 40V, Negative-QTOF	splash10-03ea-9800000000-66c017ed4ac7af48e6f1	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

2-PROPENYL-GLUCOSINOLATE

BiGG ID

Not Available

Wikipedia Link

Sinigrin

METLIN ID

Not Available

PubChem Compound

6911854

PDB ID

SZZ

ChEBI ID

9162

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1694181

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 Sinigrin (HMDB0034070)

MOL for HMDB0034070 (Sinigrin)

3D MOL for HMDB0034070 (Sinigrin)

3D SDF for HMDB0034070 (Sinigrin)

3D-SDF for HMDB0034070 (Sinigrin)

PDB for HMDB0034070 (Sinigrin)

3D PDB for HMDB0034070 (Sinigrin)

SMILES for HMDB0034070 (Sinigrin)

INCHI for HMDB0034070 (Sinigrin)

Structure for HMDB0034070 (Sinigrin)

3D Structure for HMDB0034070 (Sinigrin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra