NP-MRD: Showing NP-Card for 5-{[(2s,3r,4s,5s,6r)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium (NP0264945)

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Record Information

Version

2.0

Created at

2022-09-08 08:44:57 UTC

Updated at

2022-09-08 08:44:57 UTC

NP-MRD ID

NP0264945

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-{[(2s,3r,4s,5s,6r)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium

Description

Commelinin belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring. 5-{[(2s,3r,4s,5s,6r)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium is found in Commelina communis. 5-{[(2s,3r,4s,5s,6r)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium was first documented in 2008 (PMID: 19075517). Based on a literature review a small amount of articles have been published on Commelinin (PMID: 24891158) (PMID: 23025407) (PMID: 28242414) (PMID: 18466933).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082210442D          

 61 66  0  0  1  0            999 V2000
   -5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
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 30 31  1  0  0  0  0
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 32 33  1  0  0  0  0
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 34 35  1  6  0  0  0
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  9 60  1  0  0  0  0
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M  CHG  1  19   1
M  END

     RDKit          3D

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   -6.0292    4.3424    0.9161 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9  8  1  0
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  5  6  2  0
  5  4  1  0
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  9 10  1  0
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 11 12  1  0
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 11 56  1  0
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 14 13  2  0
 29 21  1  0
 18 55  1  0
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 47 41  1  0
 61100  1  0
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  9 67  1  1
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  4 63  1  0
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  3 62  1  0
 11 68  1  1
 54 94  1  0
 32 77  1  1
 34 78  1  1
 35 79  1  0
 35 80  1  0
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 42 83  1  0
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 45 85  1  0
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 53 93  1  0
 17 71  1  0
 16 70  1  0
 14 69  1  0
 22 72  1  0
 24 73  1  0
 26 74  1  0
 28 75  1  0
 29 76  1  0
 56 95  1  6
 57 96  1  0
 58 97  1  1
 59 98  1  0
M  CHG  1  19   1
M  END


  Mrv1652309082210442D          

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  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
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  7  8  1  0  0  0  0
  9  8  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
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 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
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 27 29  2  0  0  0  0
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 20 30  1  0  0  0  0
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 32 31  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 39 37  1  4  0  0  0
 39 40  2  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 46 47  2  0  0  0  0
 41 47  1  0  0  0  0
 34 48  1  0  0  0  0
 48 49  1  1  0  0  0
 48 50  1  0  0  0  0
 50 51  1  6  0  0  0
 50 52  1  0  0  0  0
 32 52  1  0  0  0  0
 52 53  1  1  0  0  0
 30 54  2  0  0  0  0
 54 55  1  0  0  0  0
 13 55  2  0  0  0  0
 18 55  1  0  0  0  0
 11 56  1  0  0  0  0
 56 57  1  6  0  0  0
 56 58  1  0  0  0  0
 58 59  1  1  0  0  0
 58 60  1  0  0  0  0
  9 60  1  0  0  0  0
 60 61  1  6  0  0  0
M  CHG  1  19   1
M  END
> <DATABASE_ID>
NP0264945

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](COC(=S)CC(O)=O)O[C@@H](OC2=C3C=C(O[C@@H]4O[C@H](COC(=O)C=CC5=CC=C(O)C=C5)[C@@H](O)[C@H](O)[C@H]4O)C(=[O+]C3=CC(O)=C2)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C39H38O21S/c40-17-4-1-15(2-5-17)3-6-28(46)54-13-25-31(48)33(50)36(53)39(59-25)58-24-11-19-22(56-37(24)16-7-20(42)30(47)21(43)8-16)9-18(41)10-23(19)57-38-35(52)34(51)32(49)26(60-38)14-55-29(61)12-27(44)45/h1-11,25-26,31-36,38-39,48-53H,12-14H2,(H5-,40,41,42,43,44,45,46,47)/p+1/t25-,26-,31-,32-,33+,34+,35-,36-,38-,39-/m1/s1

> <INCHI_KEY>
LAGVJTQKWJBXKY-AWJFVBHYSA-O

> <FORMULA>
C39H39O21S

> <MOLECULAR_WEIGHT>
875.78

> <EXACT_MASS>
875.16990587

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
82.31393387286126

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-{[(2S,3R,4S,5S,6R)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium

> <JCHEM_LOGP>
1.8756999999999993

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.612326166070033

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6183099371286227

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9540789955878504

> <JCHEM_POLAR_SURFACE_AREA>
345.42

> <JCHEM_REFRACTIVITY>
215.41790000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-{[(2S,3R,4S,5S,6R)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  O   UNK     0      -9.336  -5.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0      -5.335  -3.080   0.000  0.00  0.00           S+0
HETATM    7  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+1
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      16.004  -0.000   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      18.672  -0.000   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      17.338  -2.310   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   60                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   56                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   55                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   55                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   30                                                  
CONECT   21   20   22   29                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   21                                                       
CONECT   30   20   31   54                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   52                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   48                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   42   47                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   41                                                       
CONECT   48   34   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   32   53                                                  
CONECT   53   52                                                            
CONECT   54   30   55                                                       
CONECT   55   54   13   18                                                  
CONECT   56   11   57   58                                                  
CONECT   57   56                                                            
CONECT   58   56   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58    9   61                                                  
CONECT   61   60                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  132    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₉H₃₉O₂₁S

Average Mass

875.7800 Da

Monoisotopic Mass

875.16991 Da

IUPAC Name

5-{[(2S,3R,4S,5S,6R)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1lambda4-chromen-1-ylium

Traditional Name

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](COC(=S)CC(O)=O)O[C@@H](OC2=C3C=C(O[C@@H]4O[C@H](COC(=O)C=CC5=CC=C(O)C=C5)[C@@H](O)[C@H](O)[C@H]4O)C(=[O+]C3=CC(O)=C2)C2=CC(O)=C(O)C(O)=C2)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C39H38O21S/c40-17-4-1-15(2-5-17)3-6-28(46)54-13-25-31(48)33(50)36(53)39(59-25)58-24-11-19-22(56-37(24)16-7-20(42)30(47)21(43)8-16)9-18(41)10-23(19)57-38-35(52)34(51)32(49)26(60-38)14-55-29(61)12-27(44)45/h1-11,25-26,31-36,38-39,48-53H,12-14H2,(H5-,40,41,42,43,44,45,46,47)/p+1/t25-,26-,31-,32-,33+,34+,35-,36-,38-,39-/m1/s1

InChI Key

LAGVJTQKWJBXKY-AWJFVBHYSA-O

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
Commelina communis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 3-o-p-coumaroyl glycosides. These are flavonoid 3-O-glycosides where the carbohydrate moiety is esterified with a p-coumaric acid. P-coumaric acid is an organic derivative of cinnamic acid, that carries a hydroxyl group at the 4-position of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 3-O-p-coumaroyl glycosides

Alternative Parents

Substituents

Flavonoid 3-o-6-p-coumaroyl-glycoside
Anthocyanin
Anthocyanidin-5-o-glycoside
Anthocyanidin-3-o-glycoside
Flavonoid-3-o-glycoside
3'-hydroxyflavonoid
4'-hydroxyflavonoid
Hydroxyflavonoid
7-hydroxyflavonoid
Anthocyanidin
Phenolic glycoside
Coumaric acid ester
Coumaric acid or derivatives
Cinnamic acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
O-glycosyl compound
Glycosyl compound
Benzopyran
1-benzopyran
Benzenetriol
Pyrogallol derivative
Styrene
Fatty acid ester
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Oxane
Benzenoid
Dicarboxylic acid or derivatives
Fatty acyl
Monosaccharide
Monocyclic benzene moiety
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Thiocarboxylic acid ester
Carbothioic o-ester
Acetal
Oxacycle
Organoheterocyclic compound
Thiocarboxylic acid or derivatives
Polyol
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Thiocarbonyl group
Alcohol
Organosulfur compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic cation
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.88	ChemAxon
pKa (Strongest Acidic)	3.62	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	345.42 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	215.42 m³·mol⁻¹	ChemAxon
Polarizability	82.31 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

100916163

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Asada T, Koi Y, Arakawa R, Zhu F, Sadaoka M, Tamura H: Isolation techniques for anthocyanidin 3,5-diglucosides and their related chemicals using supramolecules technique, and two solid-phase extraction cartridges. J Chromatogr A. 2014 Jul 18;1351:21-8. doi: 10.1016/j.chroma.2014.05.039. Epub 2014 May 22. [PubMed:24891158 ]
Asada T, Tamura H: Isolation of bilberry anthocyanidin 3-glycosides bearing ortho-dihydroxyl groups on the B ring by forming an aluminum complex and their antioxidant activity. J Agric Food Chem. 2012 Oct 24;60(42):10634-40. doi: 10.1021/jf302476n. Epub 2012 Oct 12. [PubMed:23025407 ]
Fedenko VS, Shemet SA, Landi M: UV-vis spectroscopy and colorimetric models for detecting anthocyanin-metal complexes in plants: An overview of in vitro and in vivo techniques. J Plant Physiol. 2017 May;212:13-28. doi: 10.1016/j.jplph.2017.02.001. Epub 2017 Feb 10. [PubMed:28242414 ]
Shiono M, Matsugaki N, Takeda K: Structure of commelinin, a blue complex pigment from the blue flowers of Commelina communis. Proc Jpn Acad Ser B Phys Biol Sci. 2008;84(10):452-6. doi: 10.2183/pjab.84.452. [PubMed:19075517 ]
Mori M, Kondo T, Yoshida K: Cyanosalvianin, a supramolecular blue metalloanthocyanin, from petals of Salvia uliginosa. Phytochemistry. 2008 Dec;69(18):3151-8. doi: 10.1016/j.phytochem.2008.03.015. Epub 2008 May 6. [PubMed:18466933 ]
LOTUS database [Link]

Showing NP-Card for 5-{[(2s,3r,4s,5s,6r)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium (NP0264945)

MOL for NP0264945 (5-{[(2s,3r,4s,5s,6r)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

3D MOL for NP0264945 (5-{[(2s,3r,4s,5s,6r)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

3D SDF for NP0264945 (5-{[(2s,3r,4s,5s,6r)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

3D-SDF for NP0264945 (5-{[(2s,3r,4s,5s,6r)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

PDB for NP0264945 (5-{[(2s,3r,4s,5s,6r)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

3D PDB for NP0264945 (5-{[(2s,3r,4s,5s,6r)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

SMILES for NP0264945 (5-{[(2s,3r,4s,5s,6r)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

INCHI for NP0264945 (5-{[(2s,3r,4s,5s,6r)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

Structure for NP0264945 (5-{[(2s,3r,4s,5s,6r)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)

3D Structure for NP0264945 (5-{[(2s,3r,4s,5s,6r)-6-{[(2-carboxyethanethioyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-7-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium)