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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:57 UTC

Update Date

2022-03-07 02:53:28 UTC

HMDB ID

HMDB0032808

Secondary Accession Numbers

HMDB32808

Metabolite Identification

Common Name

Niazirinin

Description

Niazirinin 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 a significant number of articles have been published on Niazirinin.

Structure

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

HMDB0032808
     RDKit          3D
Niazirinin
 42 43  0  0  0  0  0  0  0  0999 V2000
   -5.8499    1.7944   -0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9580    0.6258   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4240   -0.4713   -0.5549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6080    0.6635    0.1429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7641   -0.4731    0.0507 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6546   -0.0817   -0.9323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2350    0.4577   -2.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8057   -1.1444   -1.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0088   -1.2539    0.0250 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7196   -0.0863    0.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0686    0.0727    0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9387   -0.9477    0.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3261   -0.7599    0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7889    0.4976    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2632    0.7326    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6923    1.0634   -0.9903 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0449    1.3355   -2.0621 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9520    1.5651    0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5861    1.3379    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8497   -1.5755    1.2365 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2303   -2.9270    1.2416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0506   -0.7113    1.3825 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9168   -1.3502    2.2865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2308    1.9663    0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6673    1.6657   -0.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2665    2.6833   -0.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2908   -1.3683   -0.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0867    0.7253   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371   -0.3490   -2.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9861    1.2142   -1.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4322    0.9530   -2.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6240   -2.1405   -0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932   -1.9521   -0.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9807   -1.6082   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8091   -0.1719    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4757    1.5320    1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3827    2.5319    0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    2.1524    0.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2029   -1.4190    2.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8050   -3.4382    0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7547    0.2988    1.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3354   -1.6395    3.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  3  0
 14 18  1  0
 18 19  2  0
  9 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22  5  1  0
 19 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  6
  6 28  1  1
  7 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  6
 12 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  1
 21 40  1  0
 22 41  1  1
 23 42  1  0
M  END


  Mrv1652309272007482D          

 23 24  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
10002.760610008.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.045810008.9453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.761010007.7082    0.0000 O   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
  7 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032808

> <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]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H19NO6/c1-9-15(22-10(2)18)13(19)14(20)16(21-9)23-12-5-3-11(4-6-12)7-8-17/h3-6,9,13-16,19-20H,7H2,1-2H3/t9-,13-,14+,15-,16-/m0/s1

> <INCHI_KEY>
QSGQMXJNFWYWMM-QOYUQHOESA-N

> <FORMULA>
C16H19NO6

> <MOLECULAR_WEIGHT>
321.329

> <EXACT_MASS>
321.121237336

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
32.32153350284303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,4S,5R,6S)-6-[4-(cyanomethyl)phenoxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate

> <ALOGPS_LOGP>
1.18

> <JCHEM_LOGP>
0.5853449339999993

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.708493314298135

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.255195545943955

> <JCHEM_PKA_STRONGEST_BASIC>
-3.691608175326495

> <JCHEM_POLAR_SURFACE_AREA>
109.00999999999999

> <JCHEM_REFRACTIVITY>
78.078

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R,6S)-6-[4-(cyanomethyl)phenoxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032808
     RDKit          3D
Niazirinin
 42 43  0  0  0  0  0  0  0  0999 V2000
   -5.8499    1.7944   -0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9580    0.6258   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4240   -0.4713   -0.5549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6080    0.6635    0.1429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7641   -0.4731    0.0507 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6546   -0.0817   -0.9323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2350    0.4577   -2.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8057   -1.1444   -1.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0088   -1.2539    0.0250 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7196   -0.0863    0.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0686    0.0727    0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9387   -0.9477    0.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3261   -0.7599    0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7889    0.4976    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2632    0.7326    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6923    1.0634   -0.9903 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0449    1.3355   -2.0621 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9520    1.5651    0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5861    1.3379    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8497   -1.5755    1.2365 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2303   -2.9270    1.2416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0506   -0.7113    1.3825 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9168   -1.3502    2.2865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2308    1.9663    0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6673    1.6657   -0.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2665    2.6833   -0.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2908   -1.3683   -0.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0867    0.7253   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371   -0.3490   -2.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9861    1.2142   -1.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4322    0.9530   -2.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6240   -2.1405   -0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932   -1.9521   -0.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9807   -1.6082   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8091   -0.1719    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4757    1.5320    1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3827    2.5319    0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    2.1524    0.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2029   -1.4190    2.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8050   -3.4382    0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7547    0.2988    1.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3354   -1.6395    3.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  3  0
 14 18  1  0
 18 19  2  0
  9 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22  5  1  0
 19 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  6
  6 28  1  1
  7 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  6
 12 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  1
 21 40  1  0
 22 41  1  1
 23 42  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
HETATM   21  C   UNK     0    8671.8208682.595   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8670.4858683.365   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8671.8218681.055   0.000  0.00  0.00           O+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   21                                                       
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                                                            
CONECT   21    7   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0032808
HETATM    1  C1  UNL     1      -5.850   1.794  -0.085  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.958   0.626  -0.174  1.00  0.00           C  
HETATM    3  O1  UNL     1      -5.424  -0.471  -0.555  1.00  0.00           O  
HETATM    4  O2  UNL     1      -3.608   0.664   0.143  1.00  0.00           O  
HETATM    5  C3  UNL     1      -2.764  -0.473   0.051  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.655  -0.082  -0.932  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.235   0.458  -2.215  1.00  0.00           C  
HETATM    8  O3  UNL     1      -0.806  -1.144  -1.129  1.00  0.00           O  
HETATM    9  C6  UNL     1      -0.009  -1.254   0.025  1.00  0.00           C  
HETATM   10  O4  UNL     1       0.720  -0.086   0.243  1.00  0.00           O  
HETATM   11  C7  UNL     1       2.069   0.073   0.261  1.00  0.00           C  
HETATM   12  C8  UNL     1       2.939  -0.948   0.056  1.00  0.00           C  
HETATM   13  C9  UNL     1       4.326  -0.760   0.079  1.00  0.00           C  
HETATM   14  C10 UNL     1       4.789   0.498   0.318  1.00  0.00           C  
HETATM   15  C11 UNL     1       6.263   0.733   0.349  1.00  0.00           C  
HETATM   16  C12 UNL     1       6.692   1.063  -0.990  1.00  0.00           C  
HETATM   17  N1  UNL     1       7.045   1.335  -2.062  1.00  0.00           N  
HETATM   18  C13 UNL     1       3.952   1.565   0.531  1.00  0.00           C  
HETATM   19  C14 UNL     1       2.586   1.338   0.501  1.00  0.00           C  
HETATM   20  C15 UNL     1      -0.850  -1.576   1.236  1.00  0.00           C  
HETATM   21  O5  UNL     1      -1.230  -2.927   1.242  1.00  0.00           O  
HETATM   22  C16 UNL     1      -2.051  -0.711   1.383  1.00  0.00           C  
HETATM   23  O6  UNL     1      -2.917  -1.350   2.286  1.00  0.00           O  
HETATM   24  H1  UNL     1      -6.231   1.966   0.940  1.00  0.00           H  
HETATM   25  H2  UNL     1      -6.667   1.666  -0.813  1.00  0.00           H  
HETATM   26  H3  UNL     1      -5.266   2.683  -0.407  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.291  -1.368  -0.293  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.087   0.725  -0.423  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.737  -0.349  -2.774  1.00  0.00           H  
HETATM   30  H7  UNL     1      -2.986   1.214  -1.952  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.432   0.953  -2.769  1.00  0.00           H  
HETATM   32  H9  UNL     1       0.624  -2.141  -0.152  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.593  -1.952  -0.135  1.00  0.00           H  
HETATM   34  H11 UNL     1       4.981  -1.608  -0.091  1.00  0.00           H  
HETATM   35  H12 UNL     1       6.809  -0.172   0.703  1.00  0.00           H  
HETATM   36  H13 UNL     1       6.476   1.532   1.095  1.00  0.00           H  
HETATM   37  H14 UNL     1       4.383   2.532   0.714  1.00  0.00           H  
HETATM   38  H15 UNL     1       1.905   2.152   0.664  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.203  -1.419   2.130  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.805  -3.438   0.513  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.755   0.299   1.742  1.00  0.00           H  
HETATM   42  H19 UNL     1      -2.335  -1.640   3.049  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   22   27
CONECT    6    7    8   28
CONECT    7   29   30   31
CONECT    8    9
CONECT    9   10   20   32
CONECT   10   11
CONECT   11   12   12   19
CONECT   12   13   33
CONECT   13   14   14   34
CONECT   14   15   18
CONECT   15   16   35   36
CONECT   16   17   17   17
CONECT   18   19   19   37
CONECT   19   38
CONECT   20   21   22   39
CONECT   21   40
CONECT   22   23   41
CONECT   23   42
END

HMDB0032808
     RDKit          3D
Niazirinin
 42 43  0  0  0  0  0  0  0  0999 V2000
   -5.8499    1.7944   -0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9580    0.6258   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4240   -0.4713   -0.5549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6080    0.6635    0.1429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7641   -0.4731    0.0507 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6546   -0.0817   -0.9323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2350    0.4577   -2.2148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8057   -1.1444   -1.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0088   -1.2539    0.0250 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7196   -0.0863    0.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0686    0.0727    0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9387   -0.9477    0.0561 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3261   -0.7599    0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7889    0.4976    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2632    0.7326    0.3489 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6923    1.0634   -0.9903 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0449    1.3355   -2.0621 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9520    1.5651    0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5861    1.3379    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8497   -1.5755    1.2365 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2303   -2.9270    1.2416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0506   -0.7113    1.3825 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9168   -1.3502    2.2865 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2308    1.9663    0.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6673    1.6657   -0.8129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2665    2.6833   -0.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2908   -1.3683   -0.2934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0867    0.7253   -0.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7371   -0.3490   -2.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9861    1.2142   -1.9517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4322    0.9530   -2.7689 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6240   -2.1405   -0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5932   -1.9521   -0.1345 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9807   -1.6082   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8091   -0.1719    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4757    1.5320    1.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3827    2.5319    0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    2.1524    0.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2029   -1.4190    2.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8050   -3.4382    0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7547    0.2988    1.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3354   -1.6395    3.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  3  0
 14 18  1  0
 18 19  2  0
  9 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22  5  1  0
 19 11  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  5 27  1  6
  6 28  1  1
  7 29  1  0
  7 30  1  0
  7 31  1  0
  9 32  1  6
 12 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  1
 21 40  1  0
 22 41  1  1
 23 42  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-[(4'-O-Acetyl-alpha-L-rhamnosyloxy)benzyl]nitrile	HMDB
4-[(4’-O-acetyl-α-L-rhamnosyloxy)benzyl]nitrile	HMDB
Niazirinine	HMDB
Niazirinin	HMDB

Chemical Formula

C₁₆H₁₉NO₆

Average Molecular Weight

321.329

Monoisotopic Molecular Weight

321.121237336

IUPAC Name

(2S,3R,4S,5R,6S)-6-[4-(cyanomethyl)phenoxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate

Traditional Name

(2S,3R,4S,5R,6S)-6-[4-(cyanomethyl)phenoxy]-4,5-dihydroxy-2-methyloxan-3-yl acetate

CAS Registry Number

1053643-44-9

SMILES

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

InChI Identifier

InChI=1S/C16H19NO6/c1-9-15(22-10(2)18)13(19)14(20)16(21-9)23-12-5-3-11(4-6-12)7-8-17/h3-6,9,13-16,19-20H,7H2,1-2H3/t9-,13-,14+,15-,16-/m0/s1

InChI Key

QSGQMXJNFWYWMM-QOYUQHOESA-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
Benzenoid
Oxane
1,2-diol
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Carbonitrile
Nitrile
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Organopnictogen compound
Organic oxide
Carbonyl group
Organonitrogen 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: HMDB0032808)
Cytoplasm (HMDB: HMDB0032808)

Brassicas (FooDB: FOOD00857)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	183 - 184 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.44 g/L	ALOGPS
logP	1.18	ALOGPS
logP	0.59	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.26	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.01 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	78.08 m³·mol⁻¹	ChemAxon
Polarizability	32.32 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]+	171.992	30932474
DeepCCS	[M-H]-	169.597	30932474
DeepCCS	[M-2H]-	203.369	30932474
DeepCCS	[M+Na]+	177.956	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Niazirinin	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O)[C@H](O)[C@H]1OC(C)=O	3208.0	Standard polar	33892256
Niazirinin	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O)[C@H](O)[C@H]1OC(C)=O	2430.0	Standard non polar	33892256
Niazirinin	C[C@@H]1O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O)[C@H](O)[C@H]1OC(C)=O	2617.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Niazirinin,1TMS,isomer #1	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O[Si](C)(C)C)[C@@H]1O	2390.2	Semi standard non polar	33892256
Niazirinin,1TMS,isomer #2	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O)[C@@H]1O[Si](C)(C)C	2402.2	Semi standard non polar	33892256
Niazirinin,2TMS,isomer #1	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	2402.7	Semi standard non polar	33892256
Niazirinin,1TBDMS,isomer #1	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2614.7	Semi standard non polar	33892256
Niazirinin,1TBDMS,isomer #2	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2626.5	Semi standard non polar	33892256
Niazirinin,2TBDMS,isomer #1	CC(=O)O[C@H]1[C@H](C)O[C@@H](OC2=CC=C(CC#N)C=C2)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2797.1	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 - Niazirinin 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 - Niazirinin 10V, Positive-QTOF	splash10-001i-0901000000-704372ba8e48aa1faa96	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niazirinin 20V, Positive-QTOF	splash10-05iu-1912000000-5cf620164ab77bd19d53	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niazirinin 40V, Positive-QTOF	splash10-0aou-4900000000-111792320d8a13b6c424	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niazirinin 10V, Negative-QTOF	splash10-03e9-0952000000-5e34681a8a9eef01d8d7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niazirinin 20V, Negative-QTOF	splash10-053r-3920000000-f32ff41584844b93ef63	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Niazirinin 40V, Negative-QTOF	splash10-0pc0-5900000000-0c2e00a44200bca22160	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

FDB010782

KNApSAcK ID

C00057116

Chemspider ID

8601625

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10426197

PDB ID

Not Available

ChEBI ID

168901

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Niazirinin (HMDB0032808)

MOL for HMDB0032808 (Niazirinin)

3D MOL for HMDB0032808 (Niazirinin)

3D SDF for HMDB0032808 (Niazirinin)

3D-SDF for HMDB0032808 (Niazirinin)

PDB for HMDB0032808 (Niazirinin)

3D PDB for HMDB0032808 (Niazirinin)

SMILES for HMDB0032808 (Niazirinin)

INCHI for HMDB0032808 (Niazirinin)

Structure for HMDB0032808 (Niazirinin)

3D Structure for HMDB0032808 (Niazirinin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra