NP-MRD: Showing NP-Card for 5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid (NP0147774)

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Record Information

Version

2.0

Created at

2022-09-02 03:26:25 UTC

Updated at

2022-09-02 03:26:25 UTC

NP-MRD ID

NP0147774

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid

Description

5-Cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid belongs to the class of organic compounds known as cyanogenic glycosides. These are glycosides in which the aglycone moiety contains a cyanide group. 5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid is found in Thalictrum aquilegiifolium. 5-Cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241511042D          

 26 26  0  0  0  0            999 V2000
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  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
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  3  0  0  0  0
 22  6  1  4  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END

     RDKit          3D

 45 45  0  0  0  0  0  0  0  0999 V2000
    5.5122    2.2118    0.5634 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4039    1.5268    1.1125 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6341    0.6390    0.4149 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8877    0.3860   -0.7834 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4829   -0.0465    1.0537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8101   -1.0133    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5165   -2.1931   -0.3191 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7611   -2.4819    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3849   -3.6834   -0.5255 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7451   -4.4516   -1.2856 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6912   -3.9998   -0.1985 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5528   -0.7920   -0.1990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0966   -1.7316   -1.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6419   -2.4897   -1.7682 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1317    0.3313    0.2571 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4613    0.5633   -0.1370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2314   -0.4901    0.2744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5715   -0.2322    0.4199 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3771   -1.4649    0.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7426   -1.2344    0.1648 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9805    0.9598   -0.4341 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3669    1.0764   -0.4931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3483    2.1790    0.2479 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6496    3.3548   -0.3923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8888    1.9027    0.4038 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4213    2.0675    1.7004 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3182    2.5390   -0.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4338    1.5836    0.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6896    3.0933    1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7933    0.6876    1.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9153   -0.6108    1.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9777   -2.8691   -0.9782 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3461   -1.8538    0.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0141   -3.6889    0.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4429    0.6694   -1.2583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8580    0.0004    1.4778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1987   -1.7461   -1.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0975   -2.2711    0.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9252   -0.9980    1.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5227    0.8140   -1.4240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5913    1.9580   -0.8750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7923    2.1808    1.2830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1714    3.9736    0.2072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3440    2.6729   -0.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0176    2.9711    1.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
  6 12  2  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 12 13  1  0
 13 14  3  0
 25 16  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  5 30  1  0
  5 31  1  0
  7 32  1  0
  8 33  1  0
 11 34  1  0
 16 35  1  6
 18 36  1  1
 19 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  6
 22 41  1  0
 23 42  1  1
 24 43  1  0
 25 44  1  6
 26 45  1  0
M  END


  Mrv1533004241511042D          

 26 26  0  0  0  0            999 V2000
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  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
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  3  0  0  0  0
 22  6  1  4  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0147774

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC(C=CC(O)=O)=C(OC1OC(CO)C(O)C(O)C1O)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C15H19NO10/c1-24-11(20)4-7(2-3-10(18)19)8(5-16)25-15-14(23)13(22)12(21)9(6-17)26-15/h2-3,9,12-15,17,21-23H,4,6H2,1H3,(H,18,19)

> <INCHI_KEY>
ZAGGPLANHIGDAL-UHFFFAOYSA-N

> <FORMULA>
C15H19NO10

> <MOLECULAR_WEIGHT>
373.314

> <EXACT_MASS>
373.100895816

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.083103528053925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid

> <ALOGPS_LOGP>
-1.36

> <JCHEM_LOGP>
-2.595293338333333

> <ALOGPS_LOGS>
-1.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.198953412523078

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.477474254609754

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092710791522

> <JCHEM_POLAR_SURFACE_AREA>
186.77

> <JCHEM_REFRACTIVITY>
83.60309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.08e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667   9.240   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   9.240   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -2.667   3.080   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667  10.780   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.001   8.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   22                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    9   19                                                  
CONECT   19   18                                                            
CONECT   20    7   21                                                       
CONECT   21   20                                                            
CONECT   22    6   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

View in JSmol

Synonyms

Value	Source
5-Cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoate	Generator

Chemical Formula

C₁₅H₁₉NO₁₀

Average Mass

373.3140 Da

Monoisotopic Mass

373.10090 Da

IUPAC Name

5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid

Traditional Name

5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)CC(C=CC(O)=O)=C(OC1OC(CO)C(O)C(O)C1O)C#N

InChI Identifier

InChI=1S/C15H19NO10/c1-24-11(20)4-7(2-3-10(18)19)8(5-16)25-15-14(23)13(22)12(21)9(6-17)26-15/h2-3,9,12-15,17,21-23H,4,6H2,1H3,(H,18,19)

InChI Key

ZAGGPLANHIGDAL-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Thalictrum aquilegifolium	LOTUS Database	35616633

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
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Hexose monosaccharide
O-glycosyl compound
Medium-chain fatty acid
Fatty acid methyl ester
Amino fatty acid
Sugar acid
Branched fatty acid
Fatty acid ester
Heterocyclic fatty acid
Hydroxy fatty acid
Fatty acyl
Unsaturated fatty acid
Oxane
Dicarboxylic acid or derivatives
Monosaccharide
Methyl ester
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Acetal
Carboxylic acid derivative
Polyol
Carboxylic acid
Oxacycle
Nitrile
Carbonitrile
Primary alcohol
Organic nitrogen compound
Organonitrogen compound
Carbonyl group
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	-1.4	ALOGPS
logP	-2.6	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	2.48	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	186.77 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	83.6 m³·mol⁻¹	ChemAxon
Polarizability	34.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid (NP0147774)

MOL for NP0147774 (5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid)

3D MOL for NP0147774 (5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid)

3D SDF for NP0147774 (5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid)

3D-SDF for NP0147774 (5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid)

PDB for NP0147774 (5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid)

3D PDB for NP0147774 (5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid)

SMILES for NP0147774 (5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid)

INCHI for NP0147774 (5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid)

Structure for NP0147774 (5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid)

3D Structure for NP0147774 (5-cyano-4-(2-methoxy-2-oxoethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}penta-2,4-dienoic acid)