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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:56 UTC

Update Date

2022-03-07 02:53:28 UTC

HMDB ID

HMDB0032807

Secondary Accession Numbers

HMDB32807

Metabolite Identification

Common Name

Niazirin

Description

Niazirin, also known as 4-rmopan, 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. Based on a literature review very few articles have been published on Niazirin.

Structure

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

HMDB0032807
     RDKit          3D
Niazirin
 37 38  0  0  0  0  0  0  0  0999 V2000
   -2.6778    2.1348   -1.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3656    1.1399   -0.6074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8686   -0.0648   -1.1449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0646   -0.6047   -0.1238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0137    0.2927    0.0491 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    0.0600   -0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786   -1.1496   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1528   -1.3437   -0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0620   -0.3379   -0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5277   -0.5606   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1030   -1.0205    0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5756   -1.3759    1.5557 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5641    0.8742   -0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2288    1.0807    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8366   -0.7650    1.1565 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6272   -2.0344    1.6657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2989   -0.4497    1.0127 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9446   -1.5409    0.4330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5810    0.7624    0.1981 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8912    1.8647    0.9986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7547    2.3442   -1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3585    1.6859   -2.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1128    3.0646   -1.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5866    1.5754    0.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7361   -1.5931   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1565   -2.0267   -0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5110   -2.3289   -1.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6291   -1.3651   -1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0203    0.3683   -1.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2883    1.6690    0.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9026    2.0742    0.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4257   -0.0492    1.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5235   -2.4306    1.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7567   -0.3121    2.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5089   -1.7921   -0.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4111    0.5636   -0.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4596    1.5908    1.7706 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  3  0
  9 13  1  0
 13 14  2  0
  4 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  2  1  0
 14  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  4 25  1  6
  7 26  1  0
  8 27  1  0
 10 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  1
 16 33  1  0
 17 34  1  1
 18 35  1  0
 19 36  1  6
 20 37  1  0
M  END


  Mrv1652309272007272D          

 20 21  0  0  0  0            999 V2000
10006.330810007.2970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10009.188710008.9461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.903910008.5337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.905010006.4726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.474810007.2970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.905010009.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.474810008.9461    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10008.475010008.5343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.760610008.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.046010008.5342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.046010007.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.760410007.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.475010007.7095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.903510008.9469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10004.189010008.5343    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10004.189010007.7094    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10004.903510007.2969    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10005.618010007.7094    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10005.618010008.5343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10010.618610008.9468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  8  1  0  0  0  0
  1 11  1  0  0  0  0
  8  2  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 19  1  0  0  0  0
 18 19  1  0  0  0  0
 18  1  1  1  0  0  0
 17  4  1  6  0  0  0
 16  5  1  6  0  0  0
 15  7  1  1  0  0  0
 14  6  1  6  0  0  0
  2  3  1  0  0  0  0
  3 20  3  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032807

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H17NO5/c1-8-11(16)12(17)13(18)14(19-8)20-10-4-2-9(3-5-10)6-7-15/h2-5,8,11-14,16-18H,6H2,1H3/t8-,11-,12+,13+,14-/m0/s1

> <INCHI_KEY>
OBJREHLZEIEGDU-CNJBRALLSA-N

> <FORMULA>
C14H17NO5

> <MOLECULAR_WEIGHT>
279.292

> <EXACT_MASS>
279.110672651

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.66514655204221

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)acetonitrile

> <ALOGPS_LOGP>
0.61

> <JCHEM_LOGP>
0.14421952366666682

> <ALOGPS_LOGS>
-1.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.22308376270566

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.208903074699583

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6122003585840474

> <JCHEM_POLAR_SURFACE_AREA>
102.94

> <JCHEM_REFRACTIVITY>
68.9265

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)acetonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032807
     RDKit          3D
Niazirin
 37 38  0  0  0  0  0  0  0  0999 V2000
   -2.6778    2.1348   -1.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3656    1.1399   -0.6074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8686   -0.0648   -1.1449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0646   -0.6047   -0.1238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0137    0.2927    0.0491 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    0.0600   -0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786   -1.1496   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1528   -1.3437   -0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0620   -0.3379   -0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5277   -0.5606   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1030   -1.0205    0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5756   -1.3759    1.5557 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5641    0.8742   -0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2288    1.0807    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8366   -0.7650    1.1565 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6272   -2.0344    1.6657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2989   -0.4497    1.0127 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9446   -1.5409    0.4330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5810    0.7624    0.1981 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8912    1.8647    0.9986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7547    2.3442   -1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3585    1.6859   -2.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1128    3.0646   -1.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5866    1.5754    0.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7361   -1.5931   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1565   -2.0267   -0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5110   -2.3289   -1.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6291   -1.3651   -1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0203    0.3683   -1.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2883    1.6690    0.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9026    2.0742    0.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4257   -0.0492    1.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5235   -2.4306    1.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7567   -0.3121    2.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5089   -1.7921   -0.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4111    0.5636   -0.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4596    1.5908    1.7706 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  3  0
  9 13  1  0
 13 14  2  0
  4 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  2  1  0
 14  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  4 25  1  6
  7 26  1  0
  8 27  1  0
 10 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  1
 16 33  1  0
 17 34  1  1
 18 35  1  0
 19 36  1  6
 20 37  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8678.4848680.288   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8683.8198683.366   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8685.1548682.596   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8675.8238678.749   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8673.1538680.288   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8675.8238684.905   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8673.1538683.366   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8682.4878682.597   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8681.1538683.368   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8679.8198682.597   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8679.8198681.058   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8681.1538680.288   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8682.4878681.058   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8675.8208683.368   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8674.4868682.597   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8674.4868681.058   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8675.8208680.288   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8677.1548681.058   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8677.1548682.597   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0    8686.4888683.367   0.000  0.00  0.00           N+0
CONECT    1   11   18                                                       
CONECT    2    8    3                                                       
CONECT    3    2   20                                                       
CONECT    4   17                                                            
CONECT    5   16                                                            
CONECT    6   14                                                            
CONECT    7   15                                                            
CONECT    8    9   13    2                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12    1                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   15   19    6                                                  
CONECT   15   14   16    7                                                  
CONECT   16   15   17    5                                                  
CONECT   17   16   18    4                                                  
CONECT   18   17   19    1                                                  
CONECT   19   14   18                                                       
CONECT   20    3                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0032807
HETATM    1  C1  UNL     1      -2.678   2.135  -1.697  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.366   1.140  -0.607  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.869  -0.065  -1.145  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.065  -0.605  -0.124  1.00  0.00           C  
HETATM    5  O2  UNL     1      -0.014   0.293   0.049  1.00  0.00           O  
HETATM    6  C4  UNL     1       1.304   0.060  -0.137  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.779  -1.150  -0.536  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.153  -1.344  -0.716  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.062  -0.338  -0.500  1.00  0.00           C  
HETATM   10  C8  UNL     1       5.528  -0.561  -0.697  1.00  0.00           C  
HETATM   11  C9  UNL     1       6.103  -1.021   0.561  1.00  0.00           C  
HETATM   12  N1  UNL     1       6.576  -1.376   1.556  1.00  0.00           N  
HETATM   13  C10 UNL     1       3.564   0.874  -0.098  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.229   1.081   0.082  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.837  -0.765   1.156  1.00  0.00           C  
HETATM   16  O3  UNL     1      -1.627  -2.034   1.666  1.00  0.00           O  
HETATM   17  C13 UNL     1      -3.299  -0.450   1.013  1.00  0.00           C  
HETATM   18  O4  UNL     1      -3.945  -1.541   0.433  1.00  0.00           O  
HETATM   19  C14 UNL     1      -3.581   0.762   0.198  1.00  0.00           C  
HETATM   20  O5  UNL     1      -3.891   1.865   0.999  1.00  0.00           O  
HETATM   21  H1  UNL     1      -3.755   2.344  -1.724  1.00  0.00           H  
HETATM   22  H2  UNL     1      -2.359   1.686  -2.663  1.00  0.00           H  
HETATM   23  H3  UNL     1      -2.113   3.065  -1.542  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.587   1.575   0.070  1.00  0.00           H  
HETATM   25  H5  UNL     1      -0.736  -1.593  -0.453  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.157  -2.027  -0.740  1.00  0.00           H  
HETATM   27  H7  UNL     1       3.511  -2.329  -1.039  1.00  0.00           H  
HETATM   28  H8  UNL     1       5.629  -1.365  -1.459  1.00  0.00           H  
HETATM   29  H9  UNL     1       6.020   0.368  -1.043  1.00  0.00           H  
HETATM   30  H10 UNL     1       4.288   1.669   0.072  1.00  0.00           H  
HETATM   31  H11 UNL     1       1.903   2.074   0.404  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.426  -0.049   1.897  1.00  0.00           H  
HETATM   33  H13 UNL     1      -2.523  -2.431   1.882  1.00  0.00           H  
HETATM   34  H14 UNL     1      -3.757  -0.312   2.026  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.509  -1.792  -0.435  1.00  0.00           H  
HETATM   36  H16 UNL     1      -4.411   0.564  -0.532  1.00  0.00           H  
HETATM   37  H17 UNL     1      -4.460   1.591   1.771  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   19   24
CONECT    3    4
CONECT    4    5   15   25
CONECT    5    6
CONECT    6    7    7   14
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   10   13
CONECT   10   11   28   29
CONECT   11   12   12   12
CONECT   13   14   14   30
CONECT   14   31
CONECT   15   16   17   32
CONECT   16   33
CONECT   17   18   19   34
CONECT   18   35
CONECT   19   20   36
CONECT   20   37
END

HMDB0032807
     RDKit          3D
Niazirin
 37 38  0  0  0  0  0  0  0  0999 V2000
   -2.6778    2.1348   -1.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3656    1.1399   -0.6074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8686   -0.0648   -1.1449 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0646   -0.6047   -0.1238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0137    0.2927    0.0491 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039    0.0600   -0.1370 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786   -1.1496   -0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1528   -1.3437   -0.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0620   -0.3379   -0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5277   -0.5606   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1030   -1.0205    0.5609 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5756   -1.3759    1.5557 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5641    0.8742   -0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2288    1.0807    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8366   -0.7650    1.1565 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6272   -2.0344    1.6657 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2989   -0.4497    1.0127 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9446   -1.5409    0.4330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5810    0.7624    0.1981 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8912    1.8647    0.9986 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7547    2.3442   -1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3585    1.6859   -2.6627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1128    3.0646   -1.5423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5866    1.5754    0.0698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7361   -1.5931   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1565   -2.0267   -0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5110   -2.3289   -1.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6291   -1.3651   -1.4590 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0203    0.3683   -1.0432 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2883    1.6690    0.0720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9026    2.0742    0.4042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4257   -0.0492    1.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5235   -2.4306    1.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7567   -0.3121    2.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5089   -1.7921   -0.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4111    0.5636   -0.5315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4596    1.5908    1.7706 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  3  0
  9 13  1  0
 13 14  2  0
  4 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19  2  1  0
 14  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  1
  4 25  1  6
  7 26  1  0
  8 27  1  0
 10 28  1  0
 10 29  1  0
 13 30  1  0
 14 31  1  0
 15 32  1  1
 16 33  1  0
 17 34  1  1
 18 35  1  0
 19 36  1  6
 20 37  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-((6-Deoxy-alpha-L-mannopyranosyl)oxy)benzeneacetonitrile	HMDB
4-(alpha-L-Rhamnosyloxy)phenylacetonitrile	HMDB
4-(Rhamnosyloxy)phenylacetonitrile	HMDB
4-RMOPAN	HMDB
4-(Α-L-rhamnosyloxy)phenylacetonitrile	HMDB
4-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]benzeneacetonitrile	HMDB
4-[(6-Deoxy-α-L-mannopyranosyl)oxy]benzeneacetonitrile	HMDB
4-[(alpha-L-Rhamnosyloxy)benzyl]nitrile	HMDB
4-[(Α-L-rhamnosyloxy)benzyl]nitrile	HMDB
Niazirine	HMDB
Niazirin	HMDB

Chemical Formula

C₁₄H₁₇NO₅

Average Molecular Weight

279.292

Monoisotopic Molecular Weight

279.110672651

IUPAC Name

2-(4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)acetonitrile

Traditional Name

2-(4-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)acetonitrile

CAS Registry Number

122001-32-5

SMILES

C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C14H17NO5/c1-8-11(16)12(17)13(18)14(19-8)20-10-4-2-9(3-5-10)6-7-15/h2-5,8,11-14,16-18H,6H2,1H3/t8-,11-,12+,13+,14-/m0/s1

InChI Key

OBJREHLZEIEGDU-CNJBRALLSA-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
Benzyl-cyanide
Phenoxy compound
Phenol ether
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Secondary alcohol
Oxacycle
Nitrile
Carbonitrile
Polyol
Acetal
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Alcohol
Organopnictogen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032807)
Cytoplasm (HMDB: HMDB0032807)

Source

Exogenous

Exogenous (HMDB: HMDB0032807)

Food

Vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	24800 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	10.4 g/L	ALOGPS
logP	0.61	ALOGPS
logP	0.14	ChemAxon
logS	-1.4	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	102.94 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.93 m³·mol⁻¹	ChemAxon
Polarizability	27.67 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
DeepCCS	[M+H]+	161.665	30932474
DeepCCS	[M-H]-	159.27	30932474
DeepCCS	[M-2H]-	193.713	30932474
DeepCCS	[M+Na]+	168.189	30932474
AllCCS	[M+H]+	167.0	32859911
AllCCS	[M+H-H2O]+	163.6	32859911
AllCCS	[M+NH4]+	170.2	32859911
AllCCS	[M+Na]+	171.1	32859911
AllCCS	[M-H]-	165.8	32859911
AllCCS	[M+Na-2H]-	165.9	32859911
AllCCS	[M+HCOO]-	166.0	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.	2.99 minutes	32390414
Predicted by Siyang on May 30, 2022	10.5827 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.83 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	77.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1474.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	248.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	116.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	82.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	373.0 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	421.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	758.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	389.0 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	1121.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	233.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	289.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	366.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	252.3 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	54.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Niazirin	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O)[C@H](O)[C@H]1O	3343.9	Standard polar	33892256
Niazirin	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O)[C@H](O)[C@H]1O	2408.2	Standard non polar	33892256
Niazirin	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O)[C@H](O)[C@H]1O	2553.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Niazirin,1TMS,isomer #1	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	2293.8	Semi standard non polar	33892256
Niazirin,1TMS,isomer #2	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	2304.4	Semi standard non polar	33892256
Niazirin,1TMS,isomer #3	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	2315.7	Semi standard non polar	33892256
Niazirin,2TMS,isomer #1	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	2344.7	Semi standard non polar	33892256
Niazirin,2TMS,isomer #2	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	2345.4	Semi standard non polar	33892256
Niazirin,2TMS,isomer #3	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2349.6	Semi standard non polar	33892256
Niazirin,3TMS,isomer #1	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	2345.8	Semi standard non polar	33892256
Niazirin,1TBDMS,isomer #1	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	2546.2	Semi standard non polar	33892256
Niazirin,1TBDMS,isomer #2	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2551.4	Semi standard non polar	33892256
Niazirin,1TBDMS,isomer #3	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2573.0	Semi standard non polar	33892256
Niazirin,2TBDMS,isomer #1	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2778.0	Semi standard non polar	33892256
Niazirin,2TBDMS,isomer #2	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2783.6	Semi standard non polar	33892256
Niazirin,2TBDMS,isomer #3	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	2788.0	Semi standard non polar	33892256
Niazirin,3TBDMS,isomer #1	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[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	2956.6	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 - Niazirin 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 - Niazirin 10V, Negative-QTOF	splash10-0059-0960000000-5b3462453408ae602e1d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niazirin 20V, Negative-QTOF	splash10-001i-2920000000-65c30c57dad6601ac4bf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niazirin 40V, Negative-QTOF	splash10-001i-1900000000-39af0537d14b2742f1ae	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niazirin 10V, Positive-QTOF	splash10-001i-0910000000-4124fecea3f21e32148a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niazirin 20V, Positive-QTOF	splash10-053u-2920000000-33208a32a87c1054048f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niazirin 40V, Positive-QTOF	splash10-0aou-6900000000-507bae8ef1a12b6b889f	2021-09-24	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

FDB010781

KNApSAcK ID

C00056952

Chemspider ID

114718

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129556

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1831751

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 Niazirin (HMDB0032807)

MOL for HMDB0032807 (Niazirin)

3D MOL for HMDB0032807 (Niazirin)

3D SDF for HMDB0032807 (Niazirin)

3D-SDF for HMDB0032807 (Niazirin)

PDB for HMDB0032807 (Niazirin)

3D PDB for HMDB0032807 (Niazirin)

SMILES for HMDB0032807 (Niazirin)

INCHI for HMDB0032807 (Niazirin)

Structure for HMDB0032807 (Niazirin)

3D Structure for HMDB0032807 (Niazirin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra