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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:27:18 UTC

Update Date

2022-03-07 02:53:49 UTC

HMDB ID

HMDB0033699

Secondary Accession Numbers

HMDB33699

Metabolite Identification

Common Name

Linamarin

Description

Linamarin, also known as phaseolunatin, belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. Linamarin exists in all living organisms, ranging from bacteria to humans. In humans, linamarin is involved in the lansoprazole metabolism pathway. Linamarin is a bitter tasting compound. Linamarin has been detected, but not quantified in, several different foods, such as spirulinas (Spirulina), celeriacs (Apium graveolens var. rapaceum), chinese cinnamons (Cinnamomum aromaticum), green beans (Phaseolus vulgaris), and tronchuda cabbages (Brassica oleracea var. costata). This could make linamarin a potential biomarker for the consumption of these foods. Linamarin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Linamarin.

Structure

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

HMDB0033699
     RDKit          3D
Linamarin
 34 34  0  0  0  0  0  0  0  0999 V2000
   -2.7493    0.6995    0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387   -0.2811   -0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7787    0.1131   -1.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464   -1.5990    0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904   -2.6504    0.5893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5030   -0.1106   -0.9395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2751   -0.2224   -0.4714 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3448    1.0426   -0.4676 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385    1.0129    0.4918 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7368    2.3744    0.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7303    2.2365    1.9334 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4771    0.2220   -0.0850 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5589    0.2023    0.7526 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9581   -1.2029   -0.2581 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9326   -1.9650   -0.9017 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6677   -1.2147   -1.0592 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1240   -2.5015   -0.8894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1610    0.3856    1.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3429    1.6712    0.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8118    0.8799    1.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4696   -0.2231   -2.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7425   -0.3048   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7859    1.2241   -1.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3477   -0.5051    0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9599    0.4473    1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8494    2.8024    1.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0027    3.0644    0.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6272    2.3950    1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7286    0.5975   -1.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1924   -0.5003    0.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8269   -1.6198    0.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5372   -2.6988   -1.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610   -1.0152   -2.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1889   -2.7560    0.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  3  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  1
  9 25  1  1
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  6
 13 30  1  0
 14 31  1  1
 15 32  1  0
 16 33  1  6
 17 34  1  0
M  END


  Mrv0541 09051416582D          

 22 22  0  0  1  0            999 V2000
    0.4125   -2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.9355    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
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  1  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  4  1  0  0  0  0
 11  4  3  0  0  0  0
 12  3  1  0  0  0  0
  6 13  1  6  0  0  0
  7 14  1  6  0  0  0
  8 15  1  6  0  0  0
 16  5  1  0  0  0  0
 16  9  1  0  0  0  0
  9 17  1  1  0  0  0
 17 10  1  0  0  0  0
  5 18  1  6  0  0  0
  6 19  1  1  0  0  0
  7 20  1  6  0  0  0
  8 21  1  1  0  0  0
  9 22  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0033699

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]1(O)[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(OC(C)(C)C#N)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C10H17NO6/c1-10(2,4-11)17-9-8(15)7(14)6(13)5(3-12)16-9/h5-9,12-15H,3H2,1-2H3/t5-,6-,7+,8-,9+/m1/s1

> <INCHI_KEY>
QLTCHMYAEJEXBT-ZEBDFXRSSA-N

> <FORMULA>
C10H17NO6

> <MOLECULAR_WEIGHT>
247.2451

> <EXACT_MASS>
247.105587281

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
23.33795162018351

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanenitrile

> <ALOGPS_LOGP>
-1.15

> <JCHEM_LOGP>
-1.7519504109999997

> <ALOGPS_LOGS>
-0.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.199265755493812

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.208435937637255

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810842497378927

> <JCHEM_POLAR_SURFACE_AREA>
123.17000000000002

> <JCHEM_REFRACTIVITY>
54.9457

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.68e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
linamarin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033699
     RDKit          3D
Linamarin
 34 34  0  0  0  0  0  0  0  0999 V2000
   -2.7493    0.6995    0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387   -0.2811   -0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7787    0.1131   -1.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464   -1.5990    0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904   -2.6504    0.5893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5030   -0.1106   -0.9395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2751   -0.2224   -0.4714 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3448    1.0426   -0.4676 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385    1.0129    0.4918 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7368    2.3744    0.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7303    2.2365    1.9334 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4771    0.2220   -0.0850 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5589    0.2023    0.7526 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9581   -1.2029   -0.2581 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9326   -1.9650   -0.9017 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6677   -1.2147   -1.0592 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1240   -2.5015   -0.8894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1610    0.3856    1.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3429    1.6712    0.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8118    0.8799    1.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4696   -0.2231   -2.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7425   -0.3048   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7859    1.2241   -1.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3477   -0.5051    0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9599    0.4473    1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8494    2.8024    1.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0027    3.0644    0.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6272    2.3950    1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7286    0.5975   -1.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1924   -0.5003    0.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8269   -1.6198    0.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5372   -2.6988   -1.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610   -1.0152   -2.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1889   -2.7560    0.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  3  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  1
  9 25  1  1
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  6
 13 30  1  0
 14 31  1  1
 15 32  1  0
 16 33  1  6
 17 34  1  0
M  END

HEADER    PROTEIN                                 05-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-14         0                                  
HETATM    1  C   UNK     0       0.770  -4.414   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.770  -1.746   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -2.667  -4.620   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       0.000   3.080   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.000  -1.540   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3    5   12                                                       
CONECT    4   10   11                                                       
CONECT    5    3    6   16   18                                             
CONECT    6    5    7   13   19                                             
CONECT    7    6    8   14   20                                             
CONECT    8    7    9   15   21                                             
CONECT    9    8   16   17   22                                             
CONECT   10    1    2    4   17                                             
CONECT   11    4                                                            
CONECT   12    3                                                            
CONECT   13    6                                                            
CONECT   14    7                                                            
CONECT   15    8                                                            
CONECT   16    5    9                                                       
CONECT   17    9   10                                                       
CONECT   18    5                                                            
CONECT   19    6                                                            
CONECT   20    7                                                            
CONECT   21    8                                                            
CONECT   22    9                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0033699
HETATM    1  C1  UNL     1      -2.749   0.699   0.849  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.639  -0.281  -0.318  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.779   0.113  -1.258  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.946  -1.599   0.198  1.00  0.00           C  
HETATM    5  N1  UNL     1      -3.190  -2.650   0.589  1.00  0.00           N  
HETATM    6  O1  UNL     1      -1.503  -0.111  -0.940  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.275  -0.222  -0.471  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.345   1.043  -0.468  1.00  0.00           O  
HETATM    9  C6  UNL     1       1.339   1.013   0.492  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.737   2.374   0.983  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.730   2.237   1.933  1.00  0.00           O  
HETATM   12  C8  UNL     1       2.477   0.222  -0.085  1.00  0.00           C  
HETATM   13  O4  UNL     1       3.559   0.202   0.753  1.00  0.00           O  
HETATM   14  C9  UNL     1       1.958  -1.203  -0.258  1.00  0.00           C  
HETATM   15  O5  UNL     1       2.933  -1.965  -0.902  1.00  0.00           O  
HETATM   16  C10 UNL     1       0.668  -1.215  -1.059  1.00  0.00           C  
HETATM   17  O6  UNL     1       0.124  -2.502  -0.889  1.00  0.00           O  
HETATM   18  H1  UNL     1      -2.161   0.386   1.711  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.343   1.671   0.444  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.812   0.880   1.044  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.470  -0.223  -2.275  1.00  0.00           H  
HETATM   22  H5  UNL     1      -4.743  -0.305  -0.940  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.786   1.224  -1.275  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.348  -0.505   0.614  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.960   0.447   1.378  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.849   2.802   1.504  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.003   3.064   0.162  1.00  0.00           H  
HETATM   28  H11 UNL     1       3.627   2.395   1.561  1.00  0.00           H  
HETATM   29  H12 UNL     1       2.729   0.598  -1.086  1.00  0.00           H  
HETATM   30  H13 UNL     1       4.192  -0.500   0.516  1.00  0.00           H  
HETATM   31  H14 UNL     1       1.827  -1.620   0.759  1.00  0.00           H  
HETATM   32  H15 UNL     1       2.537  -2.699  -1.419  1.00  0.00           H  
HETATM   33  H16 UNL     1       0.961  -1.015  -2.099  1.00  0.00           H  
HETATM   34  H17 UNL     1       0.189  -2.756   0.060  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4    6
CONECT    3   21   22   23
CONECT    4    5    5    5
CONECT    6    7
CONECT    7    8   16   24
CONECT    8    9
CONECT    9   10   12   25
CONECT   10   11   26   27
CONECT   11   28
CONECT   12   13   14   29
CONECT   13   30
CONECT   14   15   16   31
CONECT   15   32
CONECT   16   17   33
CONECT   17   34
END

HMDB0033699
     RDKit          3D
Linamarin
 34 34  0  0  0  0  0  0  0  0999 V2000
   -2.7493    0.6995    0.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387   -0.2811   -0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7787    0.1131   -1.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464   -1.5990    0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1904   -2.6504    0.5893 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5030   -0.1106   -0.9395 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2751   -0.2224   -0.4714 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3448    1.0426   -0.4676 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385    1.0129    0.4918 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7368    2.3744    0.9825 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7303    2.2365    1.9334 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4771    0.2220   -0.0850 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5589    0.2023    0.7526 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9581   -1.2029   -0.2581 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9326   -1.9650   -0.9017 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6677   -1.2147   -1.0592 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1240   -2.5015   -0.8894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1610    0.3856    1.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3429    1.6712    0.4441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8118    0.8799    1.0444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4696   -0.2231   -2.2750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7425   -0.3048   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7859    1.2241   -1.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3477   -0.5051    0.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9599    0.4473    1.3785 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8494    2.8024    1.5036 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0027    3.0644    0.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6272    2.3950    1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7286    0.5975   -1.0862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1924   -0.5003    0.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8269   -1.6198    0.7591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5372   -2.6988   -1.4188 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610   -1.0152   -2.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1889   -2.7560    0.0600 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  3  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  1
  9 25  1  1
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  6
 13 30  1  0
 14 31  1  1
 15 32  1  0
 16 33  1  6
 17 34  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1-Cyano-1-methylethyl beta-D-glucoside	ChEBI
Phaseolunatin	ChEBI
1-Cyano-1-methylethyl b-D-glucoside	Generator
1-Cyano-1-methylethyl β-D-glucoside	Generator
2-(b-D-Glucopyranosyloxy)-2-methylpropanenitrile, 9ci	HMDB
2-(beta-D-Glucopyranosyloxy)-2-methyl-propanenitrile	HMDB
2-(beta-D-Glucopyranosyloxy)-2-methylpropanenitrile	HMDB
alpha-Hydroxyisobutyronitrile-beta-D-glucose	HMDB
Manihotoxin	HMDB

Chemical Formula

C₁₀H₁₇NO₆

Average Molecular Weight

247.2451

Monoisotopic Molecular Weight

247.105587281

IUPAC Name

2-methyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanenitrile

Traditional Name

linamarin

CAS Registry Number

554-35-8

SMILES

[H][C@]1(O)[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(OC(C)(C)C#N)[C@]1([H])O

InChI Identifier

InChI=1S/C10H17NO6/c1-10(2,4-11)17-9-8(15)7(14)6(13)5(3-12)16-9/h5-9,12-15H,3H2,1-2H3/t5-,6-,7+,8-,9+/m1/s1

InChI Key

QLTCHMYAEJEXBT-ZEBDFXRSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Cyanogenic glycosides

Alternative Parents

Substituents

Cyanogenic glycoside
Hexose monosaccharide
O-glycosyl compound
Monosaccharide
Oxane
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Nitrile
Carbonitrile
Acetal
Primary alcohol
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:16441 )
Cyanogenic glucosides derived from valine or isoleucine (C01594 )

Ontology

Glucose intolerance (HMDB: HMDB0033699)

Nervous system disorder

Peripheral nervous system disorder

Motor neuron disease (HMDB: HMDB0033699)

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033699)
Cytoplasm (HMDB: HMDB0033699)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033699)

Source

Exogenous

Exogenous (HMDB: HMDB0033699)

Food

Food (HMDB: HMDB0033699)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Endogenous

Plant

Animal

Animal (HMDB: HMDB0033699)

Process

Not Available

Role

Biological role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	143 - 144 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	564900 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	66.8 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.8	ChemAxon
logS	-0.57	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	123.17 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	54.95 m³·mol⁻¹	ChemAxon
Polarizability	23.34 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
DarkChem	[M+H]+	157.257	31661259
DarkChem	[M-H]-	150.524	31661259
DeepCCS	[M+H]+	149.288	30932474
DeepCCS	[M-H]-	146.892	30932474
DeepCCS	[M-2H]-	181.016	30932474
DeepCCS	[M+Na]+	155.465	30932474
AllCCS	[M+H]+	156.4	32859911
AllCCS	[M+H-H2O]+	152.9	32859911
AllCCS	[M+NH4]+	159.7	32859911
AllCCS	[M+Na]+	160.6	32859911
AllCCS	[M-H]-	154.6	32859911
AllCCS	[M+Na-2H]-	155.0	32859911
AllCCS	[M+HCOO]-	155.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Linamarin	[H][C@]1(O)[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(OC(C)(C)C#N)[C@]1([H])O	2345.2	Standard polar	33892256
Linamarin	[H][C@]1(O)[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(OC(C)(C)C#N)[C@]1([H])O	2002.7	Standard non polar	33892256
Linamarin	[H][C@]1(O)[C@]([H])(O)[C@@]([H])(CO)O[C@@]([H])(OC(C)(C)C#N)[C@]1([H])O	1964.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Linamarin,1TMS,isomer #1	CC(C)(C#N)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	1851.1	Semi standard non polar	33892256
Linamarin,1TMS,isomer #2	CC(C)(C#N)O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	1867.1	Semi standard non polar	33892256
Linamarin,1TMS,isomer #3	CC(C)(C#N)O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	1889.1	Semi standard non polar	33892256
Linamarin,1TMS,isomer #4	CC(C)(C#N)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	1845.5	Semi standard non polar	33892256
Linamarin,2TMS,isomer #1	CC(C)(C#N)O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	1903.6	Semi standard non polar	33892256
Linamarin,2TMS,isomer #2	CC(C)(C#N)O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	1883.8	Semi standard non polar	33892256
Linamarin,2TMS,isomer #3	CC(C)(C#N)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1879.9	Semi standard non polar	33892256
Linamarin,2TMS,isomer #4	CC(C)(C#N)O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	1881.5	Semi standard non polar	33892256
Linamarin,2TMS,isomer #5	CC(C)(C#N)O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	1872.3	Semi standard non polar	33892256
Linamarin,2TMS,isomer #6	CC(C)(C#N)O[C@@H]1O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	1859.4	Semi standard non polar	33892256
Linamarin,3TMS,isomer #1	CC(C)(C#N)O[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	1929.1	Semi standard non polar	33892256
Linamarin,3TMS,isomer #2	CC(C)(C#N)O[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	1922.6	Semi standard non polar	33892256
Linamarin,3TMS,isomer #3	CC(C)(C#N)O[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	1899.9	Semi standard non polar	33892256
Linamarin,3TMS,isomer #4	CC(C)(C#N)O[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	1915.5	Semi standard non polar	33892256
Linamarin,4TMS,isomer #1	CC(C)(C#N)O[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	1946.9	Semi standard non polar	33892256
Linamarin,1TBDMS,isomer #1	CC(C)(C#N)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2098.5	Semi standard non polar	33892256
Linamarin,1TBDMS,isomer #2	CC(C)(C#N)O[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	2117.1	Semi standard non polar	33892256
Linamarin,1TBDMS,isomer #3	CC(C)(C#N)O[C@@H]1O[C@H](CO[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)[C@H]1O	2123.2	Semi standard non polar	33892256
Linamarin,1TBDMS,isomer #4	CC(C)(C#N)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2094.9	Semi standard non polar	33892256
Linamarin,2TBDMS,isomer #1	CC(C)(C#N)O[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	2372.9	Semi standard non polar	33892256
Linamarin,2TBDMS,isomer #2	CC(C)(C#N)O[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	2345.4	Semi standard non polar	33892256
Linamarin,2TBDMS,isomer #3	CC(C)(C#N)O[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	2347.2	Semi standard non polar	33892256
Linamarin,2TBDMS,isomer #4	CC(C)(C#N)O[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	2360.8	Semi standard non polar	33892256
Linamarin,2TBDMS,isomer #5	CC(C)(C#N)O[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	2341.6	Semi standard non polar	33892256
Linamarin,2TBDMS,isomer #6	CC(C)(C#N)O[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	2352.6	Semi standard non polar	33892256
Linamarin,3TBDMS,isomer #1	CC(C)(C#N)O[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	2559.7	Semi standard non polar	33892256
Linamarin,3TBDMS,isomer #2	CC(C)(C#N)O[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	2562.2	Semi standard non polar	33892256
Linamarin,3TBDMS,isomer #3	CC(C)(C#N)O[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	2542.2	Semi standard non polar	33892256
Linamarin,3TBDMS,isomer #4	CC(C)(C#N)O[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	2551.0	Semi standard non polar	33892256
Linamarin,4TBDMS,isomer #1	CC(C)(C#N)O[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	2763.2	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 - Linamarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bu0-9530000000-e58b8985888c18c2b644	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Linamarin GC-MS (4 TMS) - 70eV, Positive	splash10-00di-3121490000-6e31a29cb4593bc0a0f1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Linamarin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Linamarin 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linamarin Linear Ion Trap , negative-QTOF	splash10-014i-0940000000-bf243e2c29ff6b26fcf2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linamarin Linear Ion Trap , negative-QTOF	splash10-014i-0950000000-79243dda9f61101991c6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linamarin Linear Ion Trap , positive-QTOF	splash10-0udi-0910000000-1f3450a50f0470bcbca4	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linamarin Linear Ion Trap , positive-QTOF	splash10-0udi-0910000000-a1faa4a6e57a8ab98259	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linamarin Linear Ion Trap , positive-QTOF	splash10-0006-0390000000-dbccc3f4d1e4a414e258	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Linamarin Linear Ion Trap , positive-QTOF	splash10-0006-0390000000-790cec5ee5082b154919	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linamarin 10V, Positive-QTOF	splash10-00ks-9150000000-21a7a562083ca747be69	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linamarin 20V, Positive-QTOF	splash10-014r-9000000000-41f560bdd8b351dbae10	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linamarin 40V, Positive-QTOF	splash10-014i-9000000000-218d76388b6e2adf862b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linamarin 10V, Negative-QTOF	splash10-00l2-9260000000-8d2767506ce49eb7251a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linamarin 20V, Negative-QTOF	splash10-001i-9110000000-036fd16f5b6281c51d5b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linamarin 40V, Negative-QTOF	splash10-00lr-9000000000-2ef6f32d0883a3ce35e2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linamarin 10V, Negative-QTOF	splash10-0002-0290000000-04e466e80fc34a31711f	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linamarin 20V, Negative-QTOF	splash10-014j-9430000000-938a48430e27b76573bb	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linamarin 40V, Negative-QTOF	splash10-0api-9000000000-13d670ae474f26ad1b06	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linamarin 10V, Positive-QTOF	splash10-0002-1970000000-9f82b8d658576c297dd8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linamarin 20V, Positive-QTOF	splash10-014u-9400000000-bc1ee3aa7d00ae291fb1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Linamarin 40V, Positive-QTOF	splash10-0uxu-9000000000-b040996bb0528ff70807	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹³C 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

Not Available

BiGG ID

Not Available

Wikipedia Link

Linamarin

METLIN ID

Not Available

PubChem Compound

11128

PDB ID

Not Available

ChEBI ID

16441

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1837781

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.. .

Enzymes

Enzyme Details

1. Cytosolic beta-glucosidase

General function:: Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:: Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:: GBA3
Uniprot ID:: Q9H227
Molecular weight:: Not Available

Reactions

Linamarin + Water → Acetone cyanohydrin + D-Glucose	details

Showing metabocard for Linamarin (HMDB0033699)

MOL for HMDB0033699 (Linamarin)

3D MOL for HMDB0033699 (Linamarin)

3D SDF for HMDB0033699 (Linamarin)

3D-SDF for HMDB0033699 (Linamarin)

PDB for HMDB0033699 (Linamarin)

3D PDB for HMDB0033699 (Linamarin)

SMILES for HMDB0033699 (Linamarin)

INCHI for HMDB0033699 (Linamarin)

Structure for HMDB0033699 (Linamarin)

3D Structure for HMDB0033699 (Linamarin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions