NP-MRD: Showing NP-Card for 4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate (NP0221669)

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Record Information

Version

2.0

Created at

2022-09-05 23:18:23 UTC

Updated at

2022-09-05 23:18:23 UTC

NP-MRD ID

NP0221669

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate

Description

4-(Acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. 4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate is found in Gentiana macrophylla. Based on a literature review very few articles have been published on 4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062201182D          

 63 68  0  0  0  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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   -1.6500    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
   -0.7145   -0.4125    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
   -1.4289    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
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    0.0000    0.0000    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
   -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
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  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
 11 13  2  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
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 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
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 31 33  1  0  0  0  0
 24 33  1  0  0  0  0
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 18 35  1  0  0  0  0
 35 36  1  0  0  0  0
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  4 54  1  0  0  0  0
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 57 59  1  0  0  0  0
 59 60  1  0  0  0  0
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 61 62  1  0  0  0  0
 56 62  1  0  0  0  0
  3 62  1  0  0  0  0
 62 63  1  0  0  0  0
M  END

     RDKit          3D

107112  0  0  0  0  0  0  0  0999 V2000
   -5.3697    3.5193    1.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7446    2.4983    1.9305 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309062201182D          

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M  END
> <DATABASE_ID>
NP0221669

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1OC(OC2OC=C3C(=O)OCCC3(O)C2C=C)C(OC(=O)C2=CC=C(O)C(O)=C2)C(OC(C)=O)C1OC(=O)C1=CC=CC(OC2OC(CO)C(O)C(O)C2O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C40H44O23/c1-4-20-37(56-14-21-36(52)54-11-10-40(20,21)53)63-39-33(62-34(50)18-8-9-22(44)23(45)12-18)32(57-17(3)43)31(26(60-39)15-55-16(2)42)61-35(51)19-6-5-7-24(27(19)46)58-38-30(49)29(48)28(47)25(13-41)59-38/h4-9,12,14,20,25-26,28-33,37-39,41,44-49,53H,1,10-11,13,15H2,2-3H3

> <INCHI_KEY>
VYCHTTCUSVZEJL-UHFFFAOYSA-N

> <FORMULA>
C40H44O23

> <MOLECULAR_WEIGHT>
892.769

> <EXACT_MASS>
892.227337677

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
107

> <JCHEM_AVERAGE_POLARIZABILITY>
83.83892062897658

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate

> <JCHEM_LOGP>
0.9403117876666677

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.1198612543267

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.541064663378645

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549124198

> <JCHEM_POLAR_SURFACE_AREA>
339.49

> <JCHEM_REFRACTIVITY>
200.58670000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3H,4H,5H,6H-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -10.669   1.540   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -13.337   1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -14.670   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -16.004   1.540   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -17.338   2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0     -14.670   3.850   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -16.004   4.620   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0     -13.337   4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0     -13.337   6.160   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0     -12.003   3.850   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -10.669   4.620   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -8.002   0.000   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   62                                                  
CONECT    4    3    5   54                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   42                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15   37                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   35                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   35                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   24   34                                                  
CONECT   34   33                                                            
CONECT   35   22   18   36                                                  
CONECT   36   35                                                            
CONECT   37   14   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   37    6   43                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47   53                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   46                                                       
CONECT   54    4   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57   62                                                  
CONECT   57   56   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   56    3   63                                             
CONECT   63   62                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  136    0
END

View in JSmol

Synonyms

Value	Source
4-(Acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3H,4H,4ah,5H,6H,8H-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoic acid	Generator

Chemical Formula

C₄₀H₄₄O₂₃

Average Mass

892.7690 Da

Monoisotopic Mass

892.22734 Da

IUPAC Name

4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate

Traditional Name

4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3H,4H,5H,6H-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1OC(OC2OC=C3C(=O)OCCC3(O)C2C=C)C(OC(=O)C2=CC=C(O)C(O)=C2)C(OC(C)=O)C1OC(=O)C1=CC=CC(OC2OC(CO)C(O)C(O)C2O)=C1O

InChI Identifier

InChI=1S/C40H44O23/c1-4-20-37(56-14-21-36(52)54-11-10-40(20,21)53)63-39-33(62-34(50)18-8-9-22(44)23(45)12-18)32(57-17(3)43)31(26(60-39)15-55-16(2)42)61-35(51)19-6-5-7-24(27(19)46)58-38-30(49)29(48)28(47)25(13-41)59-38/h4-9,12,14,20,25-26,28-33,37-39,41,44-49,53H,1,10-11,13,15H2,2-3H3

InChI Key

VYCHTTCUSVZEJL-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
Gentiana macrophylla	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Phenolic glycoside
Dihydroxybenzoic acid
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
O-glycosyl compound
Glycosyl compound
Benzoate ester
Salicylic acid or derivatives
Benzoic acid or derivatives
Phenoxy compound
Phenol ether
Catechol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Delta_valerolactone
Phenol
Delta valerolactone
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Vinylogous acid
Vinylogous ester
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Primary alcohol
Organic oxygen compound
Organooxygen compound
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	0.94	ChemAxon
pKa (Strongest Acidic)	8.54	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	339.49 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	200.59 m³·mol⁻¹	ChemAxon
Polarizability	83.84 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

162896106

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate (NP0221669)

MOL for NP0221669 (4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

3D MOL for NP0221669 (4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

3D SDF for NP0221669 (4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

3D-SDF for NP0221669 (4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

PDB for NP0221669 (4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

3D PDB for NP0221669 (4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

SMILES for NP0221669 (4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

INCHI for NP0221669 (4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

Structure for NP0221669 (4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

3D Structure for NP0221669 (4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(3,4-dihydroxybenzoyloxy)-6-({4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl}oxy)oxan-3-yl 2-hydroxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)