NP-MRD: Showing NP-Card for (2r,3r,4s,5r,6s)-6-{[(3r,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-5-(acetyloxy)-2-[(acetyloxy)methyl]-4-(2,3-dihydroxybenzoyloxy)oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate (NP0291136)

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Record Information

Version

1.0

Created at

2022-09-09 22:07:00 UTC

Updated at

2022-09-09 22:07:00 UTC

NP-MRD ID

NP0291136

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(2S,3R,4S,5R,6R)-2-{[(3R,4R,4aS)-4-ethenyl-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl]oxy}-3-(acetyloxy)-6-[(acetyloxy)methyl]-5-(2-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoyloxy)oxan-4-yl 2,3-dihydroxybenzoate belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. (2r,3r,4s,5r,6s)-6-{[(3r,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-5-(acetyloxy)-2-[(acetyloxy)methyl]-4-(2,3-dihydroxybenzoyloxy)oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate is found in Gentiana macrophylla. It was first documented in 2022 (PMID: 36115695). Based on a literature review a significant number of articles have been published on (2S,3R,4S,5R,6R)-2-{[(3R,4R,4aS)-4-ethenyl-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl]oxy}-3-(acetyloxy)-6-[(acetyloxy)methyl]-5-(2-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoyloxy)oxan-4-yl 2,3-dihydroxybenzoate (PMID: 36115691) (PMID: 36115694) (PMID: 36115693) (PMID: 36115692).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102200072D          

 62 67  0  0  1  0            999 V2000
    2.1434    1.2375    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
    1.4289    0.0000    0.0000 C   0  0  2  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
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -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  2  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  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  2  0  0  0  0
  8 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  6  0  0  0
 15 14  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
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 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
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 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
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 42 43  1  1  0  0  0
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 15 58  1  0  0  0  0
 58 59  1  1  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 60 62  2  0  0  0  0
M  END

     RDKit          3D

106111  0  0  0  0  0  0  0  0999 V2000
   -7.2191   -0.1873   -2.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7990    1.0581   -2.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.0610    2.7140   -0.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5703    3.8986    0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309102200072D          

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 15 58  1  0  0  0  0
 58 59  1  1  0  0  0
 59 60  1  0  0  0  0
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 60 62  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0291136

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@@H](O[C@H]2OC=C3[C@@H](CCOC3=O)[C@H]2C=C)[C@H](OC(C)=O)[C@@H](OC(=O)C2=CC=CC(O)=C2O)[C@@H]1OC(=O)C1=CC=CC(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C40H44O22/c1-4-18-19-11-12-53-35(50)22(19)14-55-38(18)62-40-34(56-17(3)43)33(61-36(51)20-7-5-9-23(44)27(20)45)32(26(59-40)15-54-16(2)42)60-37(52)21-8-6-10-24(28(21)46)57-39-31(49)30(48)29(47)25(13-41)58-39/h4-10,14,18-19,25-26,29-34,38-41,44-49H,1,11-13,15H2,2-3H3/t18-,19+,25-,26-,29-,30+,31-,32-,33+,34-,38-,39-,40+/m1/s1

> <INCHI_KEY>
KFVRCICTFFALQS-ILUGNXPFSA-N

> <FORMULA>
C40H44O22

> <MOLECULAR_WEIGHT>
876.77

> <EXACT_MASS>
876.232423057

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
106

> <JCHEM_AVERAGE_POLARIZABILITY>
82.76929318209221

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
2.5613264076666677

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.169281185159136

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.211824195113019

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549124198

> <JCHEM_POLAR_SURFACE_AREA>
319.26

> <JCHEM_REFRACTIVITY>
199.46300000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0     -10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -9.336 -14.630   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0     -12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0     -13.337 -12.320   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0     -12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0     -13.337  -9.240   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0     -10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0     -10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      -5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -9.336   3.850   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   62  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   13                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    3   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   58                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   17   24   46                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   44                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   44                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   42                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35   37                                                       
CONECT   37   36                                                            
CONECT   38   35   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   33   43                                                  
CONECT   43   42                                                            
CONECT   44   31   27   45                                                  
CONECT   45   44                                                            
CONECT   46   23   47   58                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   56                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   54   50   57                                                  
CONECT   57   56                                                            
CONECT   58   46   15   59                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  134    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4S,5R,6R)-2-{[(3R,4R,4as)-4-ethenyl-8-oxo-3H,4H,4ah,5H,6H,8H-pyrano[3,4-c]pyran-3-yl]oxy}-3-(acetyloxy)-6-[(acetyloxy)methyl]-5-(2-hydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoyloxy)oxan-4-yl 2,3-dihydroxybenzoic acid	Generator

Chemical Formula

C₄₀H₄₄O₂₂

Average Mass

876.7700 Da

Monoisotopic Mass

876.23242 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@@H](O[C@H]2OC=C3[C@@H](CCOC3=O)[C@H]2C=C)[C@H](OC(C)=O)[C@@H](OC(=O)C2=CC=CC(O)=C2O)[C@@H]1OC(=O)C1=CC=CC(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)=C1O

InChI Identifier

InChI=1S/C40H44O22/c1-4-18-19-11-12-53-35(50)22(19)14-55-38(18)62-40-34(56-17(3)43)33(61-36(51)20-7-5-9-23(44)27(20)45)32(26(59-40)15-54-16(2)42)60-37(52)21-8-6-10-24(28(21)46)57-39-31(49)30(48)29(47)25(13-41)58-39/h4-10,14,18-19,25-26,29-34,38-41,44-49H,1,11-13,15H2,2-3H3/t18-,19+,25-,26-,29-,30+,31-,32-,33+,34-,38-,39-,40+/m1/s1

InChI Key

KFVRCICTFFALQS-ILUGNXPFSA-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
O-glycosyl compound
M-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Glycosyl compound
Salicylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Phenoxy compound
Phenol ether
Catechol
Benzoyl
Delta_valerolactone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Delta valerolactone
Sugar acid
Monosaccharide
Monocyclic benzene moiety
Oxane
Benzenoid
Vinylogous acid
Vinylogous ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
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	2.56	ChemAxon
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	319.26 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	199.46 m³·mol⁻¹	ChemAxon
Polarizability	82.77 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

163065668

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hosokawa K, Nakao S: Somatic mutations and clonal expansions in paroxysmal nocturnal hemoglobinuria. Semin Hematol. 2022 Jul;59(3):143-149. doi: 10.1053/j.seminhematol.2022.08.004. Epub 2022 Aug 22. [PubMed:36115691 ]
eBioMedicine: The dynamics of the immune system and gut in the pathophysiology of multiple sclerosis. EBioMedicine. 2022 Sep;83:104273. doi: 10.1016/j.ebiom.2022.104273. [PubMed:36115695 ]
Lundgren S, Keranen M, Wartiovaara-Kautto U, Myllymaki M: Somatic compensation of inherited bone marrow failure. Semin Hematol. 2022 Jul;59(3):167-173. doi: 10.1053/j.seminhematol.2022.07.002. Epub 2022 Aug 3. [PubMed:36115694 ]
Alcedo PE, Gutierrez-Rodrigues F, Patel BA: Somatic mutations in VEXAS Syndrome and Erdheim-Chester disease: Inflammatory myeloid diseases. Semin Hematol. 2022 Jul;59(3):156-166. doi: 10.1053/j.seminhematol.2022.07.003. Epub 2022 Aug 3. [PubMed:36115693 ]
Todisco G, Moura PL, Hellstrom-Lindberg E: Clinical manifestations of clonal hematopoiesis: What has SF3B1-mutant MDS taught us? Semin Hematol. 2022 Jul;59(3):150-155. doi: 10.1053/j.seminhematol.2022.08.002. Epub 2022 Aug 11. [PubMed:36115692 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r,4s,5r,6s)-6-{[(3r,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-5-(acetyloxy)-2-[(acetyloxy)methyl]-4-(2,3-dihydroxybenzoyloxy)oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate (NP0291136)

MOL for NP0291136 ((2r,3r,4s,5r,6s)-6-{[(3r,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-5-(acetyloxy)-2-[(acetyloxy)methyl]-4-(2,3-dihydroxybenzoyloxy)oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

3D MOL for NP0291136 ((2r,3r,4s,5r,6s)-6-{[(3r,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-5-(acetyloxy)-2-[(acetyloxy)methyl]-4-(2,3-dihydroxybenzoyloxy)oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

3D SDF for NP0291136 ((2r,3r,4s,5r,6s)-6-{[(3r,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-5-(acetyloxy)-2-[(acetyloxy)methyl]-4-(2,3-dihydroxybenzoyloxy)oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

3D-SDF for NP0291136 ((2r,3r,4s,5r,6s)-6-{[(3r,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-5-(acetyloxy)-2-[(acetyloxy)methyl]-4-(2,3-dihydroxybenzoyloxy)oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

PDB for NP0291136 ((2r,3r,4s,5r,6s)-6-{[(3r,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-5-(acetyloxy)-2-[(acetyloxy)methyl]-4-(2,3-dihydroxybenzoyloxy)oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

3D PDB for NP0291136 ((2r,3r,4s,5r,6s)-6-{[(3r,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-5-(acetyloxy)-2-[(acetyloxy)methyl]-4-(2,3-dihydroxybenzoyloxy)oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

SMILES for NP0291136 ((2r,3r,4s,5r,6s)-6-{[(3r,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-5-(acetyloxy)-2-[(acetyloxy)methyl]-4-(2,3-dihydroxybenzoyloxy)oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

INCHI for NP0291136 ((2r,3r,4s,5r,6s)-6-{[(3r,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-5-(acetyloxy)-2-[(acetyloxy)methyl]-4-(2,3-dihydroxybenzoyloxy)oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

Structure for NP0291136 ((2r,3r,4s,5r,6s)-6-{[(3r,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-5-(acetyloxy)-2-[(acetyloxy)methyl]-4-(2,3-dihydroxybenzoyloxy)oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

3D Structure for NP0291136 ((2r,3r,4s,5r,6s)-6-{[(3r,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-5-(acetyloxy)-2-[(acetyloxy)methyl]-4-(2,3-dihydroxybenzoyloxy)oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)