Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-22 20:57:05 UTC

Update Date

2021-09-22 20:57:05 UTC

HMDB ID

HMDB0301769

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Zierin

Description

Zierin is a member of the class of compounds known as cyanogenic glycosides. Cyanogenic glycosides are glycosides in which the aglycone moiety contains a cyanide group. Zierin is soluble (in water) and a very weakly acidic compound (based on its pKa). Zierin can be found in black elderberry, which makes zierin a potential biomarker for the consumption of this food product.

Structure

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

HMDB0301769
     RDKit          3D
Zierin
 39 40  0  0  0  0  0  0  0  0999 V2000
    1.3172   -4.1999    0.4408 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2832   -3.0986    0.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2306   -1.6679   -0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4136   -0.9575    0.6425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6790   -0.3417    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859   -0.9181    0.5031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797   -0.3336   -0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1383   -1.1431   -0.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0595   -0.5196   -1.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1612    1.0535    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2439    1.0208    1.0997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9512    1.6646    0.8706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9999    3.0524    0.7600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6580    1.1360    0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4728    1.7685   -0.9238 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6086   -1.1214   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7028   -1.9684    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9647   -1.4326    0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2184   -0.0885   -0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1683    0.7546   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3450    2.1466   -0.3507 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799    0.2251   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8631   -1.5802   -1.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6487   -0.5396   -1.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4402   -0.2178   -1.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122   -2.1383   -0.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5106   -1.2613    0.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6049    0.0622   -1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4361    1.6894   -0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0962    1.0685    0.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9807    1.4105    1.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2364    3.4069    1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1863    1.4548    0.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1405    2.6913   -0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4974   -3.0242    0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7977   -2.1051    0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2176    0.3301   -0.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3490    2.7662    0.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0929    0.9557   -0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  3 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 14  5  1  0
 22 16  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 21 38  1  0
 22 39  1  0
M  END

  Mrv0541 02241214492D          

 22 23  0  0  0  0            999 V2000
   -1.5979    0.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762   -0.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762   -1.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5979   -1.4693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3201   -1.0570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3201   -0.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0418    0.1803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8762    1.4693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1545    1.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1545    0.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667   -0.2320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4951   -0.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7529    0.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4951    0.6959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7529   -0.6443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2685   -0.6443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4746   -1.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0418   -1.1086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0418   -0.2320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4746   -0.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2685    0.2315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4746    0.6959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  8  9  3  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
 13 21  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301769

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1OC(OC(C#N)C2=CC(O)=CC=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H17NO7/c15-5-9(7-2-1-3-8(17)4-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2

> <INCHI_KEY>
KCVXNPDAHDGXFD-UHFFFAOYSA-N

> <FORMULA>
C14H17NO7

> <MOLECULAR_WEIGHT>
311.2873

> <EXACT_MASS>
311.100501903

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
29.134968577364333

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3-hydroxyphenyl)-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile

> <ALOGPS_LOGP>
-0.74

> <JCHEM_LOGP>
-1.1206164559999992

> <ALOGPS_LOGS>
-0.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.208730550536389

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.315240777794665

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810842650186604

> <JCHEM_POLAR_SURFACE_AREA>
143.4

> <JCHEM_REFRACTIVITY>
72.0773

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.40e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3-hydroxyphenyl)-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301769
     RDKit          3D
Zierin
 39 40  0  0  0  0  0  0  0  0999 V2000
    1.3172   -4.1999    0.4408 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2832   -3.0986    0.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2306   -1.6679   -0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4136   -0.9575    0.6425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6790   -0.3417    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859   -0.9181    0.5031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797   -0.3336   -0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1383   -1.1431   -0.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0595   -0.5196   -1.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1612    1.0535    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2439    1.0208    1.0997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9512    1.6646    0.8706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9999    3.0524    0.7600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6580    1.1360    0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4728    1.7685   -0.9238 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6086   -1.1214   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7028   -1.9684    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9647   -1.4326    0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2184   -0.0885   -0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1683    0.7546   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3450    2.1466   -0.3507 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799    0.2251   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8631   -1.5802   -1.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6487   -0.5396   -1.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4402   -0.2178   -1.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122   -2.1383   -0.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5106   -1.2613    0.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6049    0.0622   -1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4361    1.6894   -0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0962    1.0685    0.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9807    1.4105    1.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2364    3.4069    1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1863    1.4548    0.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1405    2.6913   -0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4974   -3.0242    0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7977   -2.1051    0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2176    0.3301   -0.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3490    2.7662    0.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0929    0.9557   -0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  3 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 14  5  1  0
 22 16  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 21 38  1  0
 22 39  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.983   0.337   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.636  -0.433   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.636  -1.973   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.983  -2.743   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.331  -1.973   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.331  -0.433   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.678   0.337   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      -1.636   2.743   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.288   1.876   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.288   0.337   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.058  -0.433   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.791  -0.433   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.272   0.432   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.791   1.299   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.272  -1.203   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.235  -1.203   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.619  -2.069   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.678  -2.069   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.678  -0.433   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.619  -0.433   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.235   0.432   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.619   1.299   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    8   10                                                       
CONECT   10    2    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   20                                                            
CONECT   20   16   19   21                                                  
CONECT   21   13   20   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0301769
HETATM    1  N1  UNL     1       1.317  -4.200   0.441  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.283  -3.099   0.169  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.231  -1.668  -0.177  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.414  -0.958   0.642  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.679  -0.342   0.076  1.00  0.00           C  
HETATM    6  O2  UNL     1      -1.886  -0.918   0.503  1.00  0.00           O  
HETATM    7  C4  UNL     1      -2.880  -0.334  -0.312  1.00  0.00           C  
HETATM    8  C5  UNL     1      -4.138  -1.143  -0.318  1.00  0.00           C  
HETATM    9  O3  UNL     1      -5.060  -0.520  -1.128  1.00  0.00           O  
HETATM   10  C6  UNL     1      -3.161   1.054   0.224  1.00  0.00           C  
HETATM   11  O4  UNL     1      -4.244   1.021   1.100  1.00  0.00           O  
HETATM   12  C7  UNL     1      -1.951   1.665   0.871  1.00  0.00           C  
HETATM   13  O5  UNL     1      -2.000   3.052   0.760  1.00  0.00           O  
HETATM   14  C8  UNL     1      -0.658   1.136   0.302  1.00  0.00           C  
HETATM   15  O6  UNL     1      -0.473   1.768  -0.924  1.00  0.00           O  
HETATM   16  C9  UNL     1       2.609  -1.121  -0.127  1.00  0.00           C  
HETATM   17  C10 UNL     1       3.703  -1.968   0.046  1.00  0.00           C  
HETATM   18  C11 UNL     1       4.965  -1.433   0.082  1.00  0.00           C  
HETATM   19  C12 UNL     1       5.218  -0.089  -0.045  1.00  0.00           C  
HETATM   20  C13 UNL     1       4.168   0.755  -0.214  1.00  0.00           C  
HETATM   21  O7  UNL     1       4.345   2.147  -0.351  1.00  0.00           O  
HETATM   22  C14 UNL     1       2.880   0.225  -0.252  1.00  0.00           C  
HETATM   23  H1  UNL     1       0.863  -1.580  -1.223  1.00  0.00           H  
HETATM   24  H2  UNL     1      -0.649  -0.540  -1.013  1.00  0.00           H  
HETATM   25  H3  UNL     1      -2.440  -0.218  -1.316  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.912  -2.138  -0.781  1.00  0.00           H  
HETATM   27  H5  UNL     1      -4.511  -1.261   0.705  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.605   0.062  -1.781  1.00  0.00           H  
HETATM   29  H7  UNL     1      -3.436   1.689  -0.644  1.00  0.00           H  
HETATM   30  H8  UNL     1      -5.096   1.068   0.594  1.00  0.00           H  
HETATM   31  H9  UNL     1      -1.981   1.410   1.950  1.00  0.00           H  
HETATM   32  H10 UNL     1      -1.236   3.407   1.280  1.00  0.00           H  
HETATM   33  H11 UNL     1       0.186   1.455   0.969  1.00  0.00           H  
HETATM   34  H12 UNL     1      -0.140   2.691  -0.841  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.497  -3.024   0.145  1.00  0.00           H  
HETATM   36  H14 UNL     1       5.798  -2.105   0.216  1.00  0.00           H  
HETATM   37  H15 UNL     1       6.218   0.330  -0.015  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.349   2.766   0.446  1.00  0.00           H  
HETATM   39  H17 UNL     1       2.093   0.956  -0.394  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4   16   23
CONECT    4    5
CONECT    5    6   14   24
CONECT    6    7
CONECT    7    8   10   25
CONECT    8    9   26   27
CONECT    9   28
CONECT   10   11   12   29
CONECT   11   30
CONECT   12   13   14   31
CONECT   13   32
CONECT   14   15   33
CONECT   15   34
CONECT   16   17   17   22
CONECT   17   18   35
CONECT   18   19   19   36
CONECT   19   20   37
CONECT   20   21   22   22
CONECT   21   38
CONECT   22   39
END

HMDB0301769
     RDKit          3D
Zierin
 39 40  0  0  0  0  0  0  0  0999 V2000
    1.3172   -4.1999    0.4408 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2832   -3.0986    0.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2306   -1.6679   -0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4136   -0.9575    0.6425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6790   -0.3417    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8859   -0.9181    0.5031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797   -0.3336   -0.3120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1383   -1.1431   -0.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0595   -0.5196   -1.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1612    1.0535    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2439    1.0208    1.0997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9512    1.6646    0.8706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9999    3.0524    0.7600 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6580    1.1360    0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4728    1.7685   -0.9238 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6086   -1.1214   -0.1268 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7028   -1.9684    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9647   -1.4326    0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2184   -0.0885   -0.0445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1683    0.7546   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3450    2.1466   -0.3507 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8799    0.2251   -0.2522 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8631   -1.5802   -1.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6487   -0.5396   -1.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4402   -0.2178   -1.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9122   -2.1383   -0.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5106   -1.2613    0.7048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6049    0.0622   -1.7808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4361    1.6894   -0.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0962    1.0685    0.5939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9807    1.4105    1.9502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2364    3.4069    1.2802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1863    1.4548    0.9688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1405    2.6913   -0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4974   -3.0242    0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7977   -2.1051    0.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2176    0.3301   -0.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3490    2.7662    0.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0929    0.9557   -0.3939 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  3 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 14  5  1  0
 22 16  1  0
  3 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 17 35  1  0
 18 36  1  0
 19 37  1  0
 21 38  1  0
 22 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₁₇NO₇

Average Molecular Weight

311.2873

Monoisotopic Molecular Weight

311.100501903

IUPAC Name

2-(3-hydroxyphenyl)-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile

Traditional Name

2-(3-hydroxyphenyl)-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}acetonitrile

CAS Registry Number

645-02-3

SMILES

OCC1OC(OC(C#N)C2=CC(O)=CC=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C14H17NO7/c15-5-9(7-2-1-3-8(17)4-7)21-14-13(20)12(19)11(18)10(6-16)22-14/h1-4,9-14,16-20H,6H2

InChI Key

KCVXNPDAHDGXFD-UHFFFAOYSA-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
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Secondary alcohol
Polyol
Oxacycle
Nitrile
Carbonitrile
Acetal
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Alcohol
Organopnictogen compound
Organic nitrogen compound
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0301769)

Food

Fruit

Berry

Black elderberry (FooDB: FOOD00166)

Process

Not Available

Role

Biological role

Cyanogenic (HMDB: HMDB0301769)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.74	ALOGPS
logP	-1.1	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Acidic)	9.32	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	143.4 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.08 m³·mol⁻¹	ChemAxon
Polarizability	29.13 Å³	ChemAxon
Number of Rings	2	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
AllCCS	[M+H]+	172.348	32859911
AllCCS	[M+H-H2O]+	169.126	32859911
AllCCS	[M+Na]+	176.188	32859911
AllCCS	[M+NH4]+	175.332	32859911
AllCCS	[M-H]-	168.554	32859911
AllCCS	[M+Na-2H]-	168.422	32859911
AllCCS	[M+HCOO]-	168.399	32859911
DeepCCS	[M+H]+	164.989	30932474
DeepCCS	[M-H]-	162.631	30932474
DeepCCS	[M-2H]-	195.821	30932474
DeepCCS	[M+Na]+	171.082	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zierin 10V, Positive-QTOF	splash10-0w29-0933000000-8e8f9eb16ce48cfff361	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zierin 20V, Positive-QTOF	splash10-0udi-0900000000-37ae884f664a82ef2199	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zierin 40V, Positive-QTOF	splash10-0uka-3900000000-7a1d6ee3bff6412cff0c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zierin 10V, Negative-QTOF	splash10-03dj-1928000000-e7d3c4664c7354844939	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zierin 20V, Negative-QTOF	splash10-0002-2910000000-a8c7a054c439e826ebe5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zierin 40V, Negative-QTOF	splash10-0007-9800000000-130e0e9678832a365f34	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zierin 10V, Positive-QTOF	splash10-01q9-0906000000-43ba72eb84bf07cb7795	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zierin 20V, Positive-QTOF	splash10-001i-0911000000-50c6090773e2066032bb	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zierin 40V, Positive-QTOF	splash10-0gc0-3900000000-6b42022a626ad7cd2bea	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zierin 10V, Negative-QTOF	splash10-03di-0907000000-4980c5897af00e5c5a44	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zierin 20V, Negative-QTOF	splash10-0hh9-1901000000-7487f530c20cdc70a084	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zierin 40V, Negative-QTOF	splash10-0005-6900000000-07a51ba266fc9e3738c1	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3677433

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4479458

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Zierin (HMDB0301769)

MOL for HMDB0301769 (Zierin)

3D MOL for HMDB0301769 (Zierin)

3D SDF for HMDB0301769 (Zierin)

3D-SDF for HMDB0301769 (Zierin)

PDB for HMDB0301769 (Zierin)

3D PDB for HMDB0301769 (Zierin)

SMILES for HMDB0301769 (Zierin)

INCHI for HMDB0301769 (Zierin)

Structure for HMDB0301769 (Zierin)

3D Structure for HMDB0301769 (Zierin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra