MiMeDB: Showing metabocard for Leucopelargonidin (MMDBc0053416)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:23:52 UTC

Update Date

2025-01-16 02:03:31 UTC

Metabolite ID

MMDBc0053416

Metabolite Identification

Common Name

Leucopelargonidin

Description

Leucopelargonidin (CAS: 520-17-2) is a colourless chemical compound belonging to the family of leucoanthocyanidins. Leucoanthocyanidins are flavonoids consisting of a flavan (3,4-dihydro-2-phenyl-2H-1-benzopyran) moiety that carries two hydroxy groups at the C3- and C4-positions. Leucopelargonidin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Leucopelargonidin can be found in a number of food items such as narrowleaf cattail, pepper (C. pubescens), macadamia nut (M. tetraphylla), and abiyuch, which makes leucopelargonidin a potential biomarker for the consumption of these food products (FooDB). Leucopelargonidin can also be found in Albizia lebbeck (East Indian walnut), in the fruit of Anacardium occidentale (cashew), in the fruit of Areca catechu (Areca nut), in the fruit of Hydnocarpus wightiana (Hindi Chaulmoogra), in the rhizome of Rumex hymenosepalus (Arizona dock), in Zea Mays (corn), and in Ziziphus jujuba (Chinese date) (Wikipedia ).

Structure

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

HMDB0032322
     RDKit          3D
Leucopelargonidin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -6.0782   -0.6867   -0.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7329   -0.4045   -0.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2666    0.8882   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9051    1.1378   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0078    0.1411   -0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802    0.3011    0.2143 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1282   -0.6179   -0.6323 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4885   -0.7358   -0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1997   -1.8926   -0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577   -2.0113   -0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2212   -3.1893   -0.6809 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2210   -0.8896    0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5362    0.2819    0.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2336    1.3926    0.7380 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1551    0.3657    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738    1.6483    0.3124 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7464    1.9721    1.6541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0005    1.6502    0.0399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6479    2.5705    0.8981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5047   -1.1621   -0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8275   -1.4197   -0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3892   -1.6472   -0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9754    1.6841   -0.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5773    2.1607   -0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4002    0.0140    1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6410   -2.7425   -1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7030   -3.9852   -1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3066   -0.9242    0.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2242    1.3767    0.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9725    2.4736   -0.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5627    1.1711    2.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1644    2.0543   -0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2717    3.4750    0.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8485   -2.0114    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1935   -2.4391   -0.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  5 20  1  0
 20 21  2  0
 21  2  1  0
 18  6  1  0
 15  8  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  1
  9 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 16 30  1  6
 17 31  1  0
 18 32  1  6
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  END


  Mrv1652306222023492D          

 24 26  0  0  1  0            999 V2000
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   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
    0.0000   -1.6500    0.0000 C   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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  7  1  2  0  0  0  0
  7  2  1  0  0  0  0
  8  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  7  1  6  0  0  0
 15 14  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  1  0  0  0  0
 13 19  1  1  0  0  0
 14 20  1  1  0  0  0
 21 11  1  0  0  0  0
 21 15  1  0  0  0  0
 13 22  1  6  0  0  0
 14 23  1  6  0  0  0
 15 24  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0053416

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(O)C2=C(O)C=C(O)C=C2O[C@]([H])(C2=CC=C(O)C=C2)[C@@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,13-20H/t13-,14-,15+/m0/s1

> <INCHI_KEY>
FSVMLWOLZHGCQX-SOUVJXGZSA-N

> <FORMULA>
C15H14O6

> <MOLECULAR_WEIGHT>
290.2681

> <EXACT_MASS>
290.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.686175832384908

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,4S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol

> <ALOGPS_LOGP>
0.62

> <JCHEM_LOGP>
1.1796761899999997

> <ALOGPS_LOGS>
-2.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.676464251917093

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.076158826450078

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6966911644664213

> <JCHEM_POLAR_SURFACE_AREA>
110.38000000000001

> <JCHEM_REFRACTIVITY>
73.22630000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.84e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cis-3,4-leucopelargonidin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032322
     RDKit          3D
Leucopelargonidin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -6.0782   -0.6867   -0.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7329   -0.4045   -0.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2666    0.8882   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9051    1.1378   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0078    0.1411   -0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802    0.3011    0.2143 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1282   -0.6179   -0.6323 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4885   -0.7358   -0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1997   -1.8926   -0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577   -2.0113   -0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2212   -3.1893   -0.6809 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2210   -0.8896    0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5362    0.2819    0.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2336    1.3926    0.7380 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1551    0.3657    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738    1.6483    0.3124 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7464    1.9721    1.6541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0005    1.6502    0.0399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6479    2.5705    0.8981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5047   -1.1621   -0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8275   -1.4197   -0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3892   -1.6472   -0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9754    1.6841   -0.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5773    2.1607   -0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4002    0.0140    1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6410   -2.7425   -1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7030   -3.9852   -1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3066   -0.9242    0.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2242    1.3767    0.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9725    2.4736   -0.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5627    1.1711    2.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1644    2.0543   -0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2717    3.4750    0.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8485   -2.0114    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1935   -2.4391   -0.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  5 20  1  0
 20 21  2  0
 21  2  1  0
 18  6  1  0
 15  8  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  1
  9 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 16 30  1  6
 17 31  1  0
 18 32  1  6
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  END

HEADER    PROTEIN                                 22-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-20         0                                  
HETATM    1  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       1.334  -3.850   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       4.001  -3.850   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       5.335  -1.540   0.000  0.00  0.00           H+0
CONECT    1    3    7                                                       
CONECT    2    4    7                                                       
CONECT    3    1    8                                                       
CONECT    4    2    8                                                       
CONECT    5    9   10                                                       
CONECT    6    9   11                                                       
CONECT    7    1    2   15                                                  
CONECT    8    3    4   16                                                  
CONECT    9    5    6   17                                                  
CONECT   10    5   12   18                                                  
CONECT   11    6   12   21                                                  
CONECT   12   10   11   13                                                  
CONECT   13   12   14   19   22                                             
CONECT   14   13   15   20   23                                             
CONECT   15    7   14   21   24                                             
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   10                                                            
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21   11   15                                                       
CONECT   22   13                                                            
CONECT   23   14                                                            
CONECT   24   15                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0032322
HETATM    1  O1  UNL     1      -6.078  -0.687  -0.621  1.00  0.00           O  
HETATM    2  C1  UNL     1      -4.733  -0.404  -0.421  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.267   0.888  -0.435  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.905   1.138  -0.229  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.008   0.141  -0.013  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.580   0.301   0.214  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.128  -0.618  -0.632  1.00  0.00           O  
HETATM    8  C6  UNL     1       1.489  -0.736  -0.421  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.200  -1.893  -0.649  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.558  -2.011  -0.438  1.00  0.00           C  
HETATM   11  O3  UNL     1       4.221  -3.189  -0.681  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.221  -0.890   0.030  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.536   0.282   0.267  1.00  0.00           C  
HETATM   14  O4  UNL     1       4.234   1.393   0.738  1.00  0.00           O  
HETATM   15  C11 UNL     1       2.155   0.366   0.041  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.474   1.648   0.312  1.00  0.00           C  
HETATM   17  O5  UNL     1       1.746   1.972   1.654  1.00  0.00           O  
HETATM   18  C13 UNL     1      -0.001   1.650   0.040  1.00  0.00           C  
HETATM   19  O6  UNL     1      -0.648   2.571   0.898  1.00  0.00           O  
HETATM   20  C14 UNL     1      -2.505  -1.162  -0.004  1.00  0.00           C  
HETATM   21  C15 UNL     1      -3.827  -1.420  -0.202  1.00  0.00           C  
HETATM   22  H1  UNL     1      -6.389  -1.647  -0.605  1.00  0.00           H  
HETATM   23  H2  UNL     1      -4.975   1.684  -0.606  1.00  0.00           H  
HETATM   24  H3  UNL     1      -2.577   2.161  -0.251  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.400   0.014   1.297  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.641  -2.743  -1.013  1.00  0.00           H  
HETATM   27  H6  UNL     1       3.703  -3.985  -1.021  1.00  0.00           H  
HETATM   28  H7  UNL     1       5.307  -0.924   0.217  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.224   1.377   0.914  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.973   2.474  -0.277  1.00  0.00           H  
HETATM   31  H10 UNL     1       1.563   1.171   2.239  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.164   2.054  -0.985  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.272   3.475   0.672  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.848  -2.011   0.162  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.194  -2.439  -0.191  1.00  0.00           H  
CONECT    1    2   22
CONECT    2    3    3   21
CONECT    3    4   23
CONECT    4    5    5   24
CONECT    5    6   20
CONECT    6    7   18   25
CONECT    7    8
CONECT    8    9    9   15
CONECT    9   10   26
CONECT   10   11   12   12
CONECT   11   27
CONECT   12   13   28
CONECT   13   14   15   15
CONECT   14   29
CONECT   15   16
CONECT   16   17   18   30
CONECT   17   31
CONECT   18   19   32
CONECT   19   33
CONECT   20   21   21   34
CONECT   21   35
END

HMDB0032322
     RDKit          3D
Leucopelargonidin
 35 37  0  0  0  0  0  0  0  0999 V2000
   -6.0782   -0.6867   -0.6212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7329   -0.4045   -0.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2666    0.8882   -0.4347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9051    1.1378   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0078    0.1411   -0.0133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5802    0.3011    0.2143 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1282   -0.6179   -0.6323 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4885   -0.7358   -0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1997   -1.8926   -0.6486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5577   -2.0113   -0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2212   -3.1893   -0.6809 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2210   -0.8896    0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5362    0.2819    0.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2336    1.3926    0.7380 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1551    0.3657    0.0415 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4738    1.6483    0.3124 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7464    1.9721    1.6541 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0005    1.6502    0.0399 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6479    2.5705    0.8981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5047   -1.1621   -0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8275   -1.4197   -0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3892   -1.6472   -0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9754    1.6841   -0.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5773    2.1607   -0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4002    0.0140    1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6410   -2.7425   -1.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7030   -3.9852   -1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3066   -0.9242    0.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2242    1.3767    0.9137 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9725    2.4736   -0.2771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5627    1.1711    2.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1644    2.0543   -0.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2717    3.4750    0.6717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8485   -2.0114    0.1624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1935   -2.4391   -0.1913 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
  5 20  1  0
 20 21  2  0
 21  2  1  0
 18  6  1  0
 15  8  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  1
  9 26  1  0
 11 27  1  0
 12 28  1  0
 14 29  1  0
 16 30  1  6
 17 31  1  0
 18 32  1  6
 19 33  1  0
 20 34  1  0
 21 35  1  0
M  END

Synonyms

Value	Source
(+)-Leucopelargonidin	ChEBI
(2R,3S,4S)-3,4-Leucopelargonidin	ChEBI
3,4-cis-Leucopelargonidine	HMDB
(2R,3S,4S)-Leucopelargonidin	HMDB
3,4,4',5,7-Flavanpentol	HMDB
Goratensidin	HMDB
Leucopelargonidine	HMDB
Leucopelargonidol	HMDB
Leucopelargonidin	HMDB

Molecular Formula

C₁₅H₁₄O₆

Average Mass

290.2681

Monoisotopic Mass

290.07903818

IUPAC Name

(2R,3S,4S)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol

Traditional Name

cis-3,4-leucopelargonidin

CAS Registry Number

Not Available

SMILES

[H][C@]1(O)C2=C(O)C=C(O)C=C2O[C@]([H])(C2=CC=C(O)C=C2)[C@@]1([H])O

InChI Identifier

InChI=1S/C15H14O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,13-20H/t13-,14-,15+/m0/s1

InChI Key

FSVMLWOLZHGCQX-SOUVJXGZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leucoanthocyanidins. These are flavonoids consisting of a flavan (3,4-dihydro-2-phenyl-2H-1-benzopyran) moiety that carries two hydroxy groups at the C3- and C4-positions.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Leucoanthocyanidins

Alternative Parents

Substituents

Leucoanthocyanidin-skeleton
3-hydroxyflavonoid
4'-hydroxyflavonoid
4-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Chromane
Benzopyran
1-benzopyran
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
1,2-diol
Secondary alcohol
Organoheterocyclic compound
Ether
Polyol
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

leucoanthocyanidin (CHEBI:17343 )
pentahydroxyflavan (CHEBI:17343 )
Flavan 3,4-diols (C03648 )

Functional Ontology

Not Available

Physical Properties

State

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.84 g/L	ALOGPS
logP	0.62	ALOGPS
logP	1.18	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	9.08	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.23 m³·mol⁻¹	ChemAxon
Polarizability	28.69 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0970000000-3e60660dfaca3137796c	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-000i-2100069000-3ce0116528533bd0d171	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0190000000-8b627d02db62b9f1f86c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abc-0950000000-2b74806e03f640f7e796	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05g0-4900000000-59f4d5454c4db4612e0c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0290000000-6d8231aab24727e61b96	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-1970000000-922a65848e2bfc3f1481	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6u-5910000000-09cf6f8f89aea7db38a8	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-2d980c515d025d58a6fa	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0920000000-c778de7956c2638ac4b9	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fvu-3910000000-a7264b9a10375865f13c	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-4a887fee01b47595208a	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-0910000000-788fd5f61f426f40a462	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-3900000000-181b5d47afc5e25b536c	2021-09-23	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Other Exposures

Source Type	Activity	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0032322

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

LEUCOPELARGONIDIN-CMPD

BiGG ID

Not Available

Wikipedia Link

Leucopelargonidin

METLIN ID

Not Available

PubChem Compound

440073

PDB ID

Not Available

ChEBI ID

17343

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for Leucopelargonidin (MMDBc0053416)

MOL for #<Metabolite:0x00007fca141546c8>

3D MOL for #<Metabolite:0x00007fca141546c8>

3D SDF for #<Metabolite:0x00007fca141546c8>

3D-SDF for #<Metabolite:0x00007fca141546c8>

PDB for #<Metabolite:0x00007fca141546c8>

3D PDB for #<Metabolite:0x00007fca141546c8>

SMILES for #<Metabolite:0x00007fca141546c8>

INCHI for #<Metabolite:0x00007fca141546c8>

Structure for #<Metabolite:0x00007fca141546c8>

3D Structure for #<Metabolite:0x00007fca141546c8>