NP-MRD: Showing NP-Card for (2r,3r,4s,5r,6s)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate (NP0281105)

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Record Information

Version

2.0

Created at

2022-09-09 07:15:09 UTC

Updated at

2022-09-09 07:15:09 UTC

NP-MRD ID

NP0281105

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Trifloroside belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. Trifloroside is an extremely weak basic (essentially neutral) compound (based on its pKa). (2r,3r,4s,5r,6s)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]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 algida, Gentiana gelida, Gentiana linearis, Gentiana lutea, Gentiana macrophylla, Gentiana olivieri, Gentiana scabra, Gentiana siphonantha and Gentiana tibetica. (2r,3r,4s,5r,6s)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate was first documented in 2013 (PMID: 23599008). It is a component of Gentiana scabra root extract, which is used as an internal remedy in traditional Korean medicine for the treatment of diabetes mellitus (PMID: 26129938) (PMID: 32182812) (PMID: 29149084) (PMID: 28933978).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272006302D          

 57 61  0  0  0  0            999 V2000
10000.355510000.0133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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10001.784810000.0133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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10000.349310001.6510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  6  7  1  0  0  0  0
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 33 27  2  0  0  0  0
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  2 53  1  0  0  0  0
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 57  5  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309272006302D          

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 9998.917910001.6510    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 9998.203410000.4134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.917910000.0010    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 9999.632410001.2385    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10004.6475 9999.2014    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10003.9330 9998.7889    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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10001.7841 9997.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 49 50  1  0  0  0  0
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 45 11  1  1  0  0  0
 40 15  1  6  0  0  0
 41 24  1  0  0  0  0
 41 29  1  6  0  0  0
 43 19  1  1  0  0  0
 47  5  1  1  0  0  0
 49  6  1  1  0  0  0
 50 10  1  6  0  0  0
 51  9  1  1  0  0  0
 46  8  1  6  0  0  0
 52 53  2  0  0  0  0
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 54 55  2  0  0  0  0
 55 56  1  0  0  0  0
 56 57  2  0  0  0  0
 57 52  1  0  0  0  0
  2 53  1  0  0  0  0
 52  4  1  0  0  0  0
 57  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281105

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(O[C@@H]2OC=C3C(=O)OCC[C@@]3([H])[C@H]2C=C)O[C@H](COC(C)=O)[C@@H](OC(=O)C2=C(O)C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2)[C@H](OC(C)=O)[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C35H42O20/c1-5-17-18-9-10-46-31(44)20(18)12-48-33(17)55-35-30(50-16(4)39)29(49-15(3)38)28(23(53-35)13-47-14(2)37)54-32(45)19-7-6-8-21(24(19)40)51-34-27(43)26(42)25(41)22(11-36)52-34/h5-8,12,17-18,22-23,25-30,33-36,40-43H,1,9-11,13H2,2-4H3/t17-,18+,22-,23-,25-,26+,27-,28-,29+,30-,33+,34-,35+/m1/s1

> <INCHI_KEY>
RMBMLYUFYBZPCX-XQARLGSBSA-N

> <FORMULA>
C35H42O20

> <MOLECULAR_WEIGHT>
782.701

> <EXACT_MASS>
782.226943752

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
97

> <JCHEM_AVERAGE_POLARIZABILITY>
74.41494709528959

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.92

> <JCHEM_LOGP>
0.46428261266666815

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.203392311128871

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.112257139746362

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923549124198

> <JCHEM_POLAR_SURFACE_AREA>
278.79999999999995

> <JCHEM_REFRACTIVITY>
174.83069999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5R,6S)-6-{[(3S,4R,4aS)-4-ethenyl-8-oxo-3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]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                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8667.3308666.691   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8667.3308665.151   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8665.9958664.384   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8669.9988666.691   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8672.6628665.151   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8675.3388660.555   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8676.6868659.809   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8675.3388666.715   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8678.0108665.175   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8678.0268662.121   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8667.3198669.749   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8668.6628669.002   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8669.9988669.772   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8668.6628667.462   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8664.6478671.289   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0    8665.9808672.059   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8667.3158671.289   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    8665.9808673.599   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0    8664.6478664.789   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0    8663.2988664.044   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0    8663.2988662.504   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8664.6318661.732   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0    8661.9648661.732   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0    8661.9798669.749   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0    8659.3168671.292   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8660.6498672.066   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0    8656.6568665.110   0.000  0.00  0.00           O+0
HETATM   28  H   UNK     0    8657.9868670.519   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0    8663.3138670.519   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0    8656.6568669.742   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8655.3228668.972   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0    8655.3228667.432   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0    8656.6568666.662   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8659.3178669.742   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0    8657.9838668.972   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0    8657.9838667.432   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0    8659.3178666.662   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0    8660.6518667.432   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0    8660.6518668.972   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0    8664.6478669.749   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0    8663.3138668.979   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0    8663.3138667.438   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0    8664.6478666.669   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0    8665.9808667.438   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0    8665.9808668.979   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0    8675.3428665.176   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0    8674.0088664.406   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0    8674.0088662.866   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0    8675.3428662.096   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0    8676.6768662.866   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0    8676.6768664.406   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0    8669.9978665.153   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0    8668.6638664.383   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0    8668.6638662.843   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0    8669.9978662.073   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0    8671.3318662.843   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0    8671.3318664.383   0.000  0.00  0.00           C+0
CONECT    1    2   44                                                       
CONECT    2    1    3   53                                                  
CONECT    3    2                                                            
CONECT    4   52                                                            
CONECT    5   47   57                                                       
CONECT    6    7   49                                                       
CONECT    7    6                                                            
CONECT    8   46                                                            
CONECT    9   51                                                            
CONECT   10   50                                                            
CONECT   11   12   45                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   16   40                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   20   43                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   39   41                                                       
CONECT   25   26   34                                                       
CONECT   26   25                                                            
CONECT   27   33                                                            
CONECT   28   35                                                            
CONECT   29   41                                                            
CONECT   30   31   35                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   27   36                                                  
CONECT   34   35   39   25                                                  
CONECT   35   34   36   30   28                                             
CONECT   36   35   37   33                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   34   38   24                                                  
CONECT   40   41   45   15                                                  
CONECT   41   40   42   24   29                                             
CONECT   42   41   43                                                       
CONECT   43   44   42   19                                                  
CONECT   44   43   45    1                                                  
CONECT   45   40   44   11                                                  
CONECT   46   47   51    8                                                  
CONECT   47   46   48    5                                                  
CONECT   48   47   49                                                       
CONECT   49   50   48    6                                                  
CONECT   50   49   51   10                                                  
CONECT   51   46   50    9                                                  
CONECT   52   53   57    4                                                  
CONECT   53   52   54    2                                                  
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   52    5                                                  
MASTER        0    0    0    0    0    0    0    0   57    0  122    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₅H₄₂O₂₀

Average Mass

782.7010 Da

Monoisotopic Mass

782.22694 Da

IUPAC Name

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

[H][C@@]1(O[C@@H]2OC=C3C(=O)OCC[C@@]3([H])[C@H]2C=C)O[C@H](COC(C)=O)[C@@H](OC(=O)C2=C(O)C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC=C2)[C@H](OC(C)=O)[C@H]1OC(C)=O

InChI Identifier

InChI=1S/C35H42O20/c1-5-17-18-9-10-46-31(44)20(18)12-48-33(17)55-35-30(50-16(4)39)29(49-15(3)38)28(23(53-35)13-47-14(2)37)54-32(45)19-7-6-8-21(24(19)40)51-34-27(43)26(42)25(41)22(11-36)52-34/h5-8,12,17-18,22-23,25-30,33-36,40-43H,1,9-11,13H2,2-4H3/t17-,18+,22-,23-,25-,26+,27-,28-,29+,30-,33+,34-,35+/m1/s1

InChI Key

RMBMLYUFYBZPCX-XQARLGSBSA-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 algida	LOTUS Database	35616633
Gentiana gelida	LOTUS Database	35616633
Gentiana linearis	LOTUS Database	35616633
Gentiana lutea	LOTUS Database	35616633
Gentiana macrophylla	LOTUS Database	35616633
Gentiana olivieri	LOTUS Database	35616633
Gentiana scabra	LOTUS Database	35616633
Gentiana siphonantha	LOTUS Database	35616633
Gentiana tibetica	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-hydroxybenzoic acid ester
Glycosyl compound
O-glycosyl compound
Benzoate ester
Salicylic acid or derivatives
Benzoic acid or derivatives
Phenoxy compound
Benzoyl
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
Delta valerolactone
Delta_valerolactone
Phenol
Sugar acid
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Vinylogous acid
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Secondary alcohol
Carboxylic acid ester
Polyol
Organoheterocyclic compound
Oxacycle
Acetal
Primary alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
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	0.92	ALOGPS
logP	0.46	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	10.11	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	278.8 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	174.83 m³·mol⁻¹	ChemAxon
Polarizability	74.41 Å³	ChemAxon
Number of Rings	5	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

C00010796

Chemspider ID

58163574

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101688128

PDB ID

Not Available

ChEBI ID

132850

Good Scents ID

Not Available

References

General References

Suh HW, Lee KB, Kim KS, Yang HJ, Choi EK, Shin MH, Park YS, Na YC, Ahn KS, Jang YP, Um JY, Jang HJ: A bitter herbal medicine Gentiana scabra root extract stimulates glucagon-like peptide-1 secretion and regulates blood glucose in db/db mouse. J Ethnopharmacol. 2015 Aug 22;172:219-26. doi: 10.1016/j.jep.2015.06.042. Epub 2015 Jun 28. [PubMed:26129938 ]
Zhang G, Li Y, Wei W, Li J, Li H, Huang Y, Guo DA: Metabolomics Combined with Multivariate Statistical Analysis for Screening of Chemical Markers between Gentiana scabra and Gentiana rigescens. Molecules. 2020 Mar 9;25(5). pii: molecules25051228. doi: 10.3390/molecules25051228. [PubMed:32182812 ]
Chen B, Peng Y, Wang X, Li Z, Sun Y: Preparative Separation and Purification of Four Glycosides from Gentianae radix by High-Speed Counter-Current Chromatography and Comparison of Their Anti-NO Production Effects. Molecules. 2017 Nov 17;22(11). pii: molecules22112002. doi: 10.3390/molecules22112002. [PubMed:29149084 ]
Yang EJ, Lee JG, Song KS: The Glycosidase Treatment of Gentianae Scabrae Radix Converts Trifloroside into Deglucosyltrifloroside with an Enhancement of Antioxidative Effects. J Med Food. 2017 Oct;20(10):951-958. doi: 10.1089/jmf.2017.3938. Epub 2017 Sep 21. [PubMed:28933978 ]
Wang S, Xu Y, Jiang W, Zhang Y: Isolation and identification of constituents with activity of inhibiting nitric oxide production in RAW 264.7 macrophages from Gentiana triflora. Planta Med. 2013 May;79(8):680-6. doi: 10.1055/s-0032-1328460. Epub 2013 Apr 18. [PubMed:23599008 ]
LOTUS database [Link]

Showing NP-Card for (2r,3r,4s,5r,6s)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate (NP0281105)

MOL for NP0281105 ((2r,3r,4s,5r,6s)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]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 NP0281105 ((2r,3r,4s,5r,6s)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]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 NP0281105 ((2r,3r,4s,5r,6s)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]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 NP0281105 ((2r,3r,4s,5r,6s)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

PDB for NP0281105 ((2r,3r,4s,5r,6s)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]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 NP0281105 ((2r,3r,4s,5r,6s)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

SMILES for NP0281105 ((2r,3r,4s,5r,6s)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

INCHI for NP0281105 ((2r,3r,4s,5r,6s)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)

Structure for NP0281105 ((2r,3r,4s,5r,6s)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]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 NP0281105 ((2r,3r,4s,5r,6s)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]oxan-3-yl 2-hydroxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzoate)