NP-MRD: Showing NP-Card for [(4r,5s,7r,8r,11s,12s,13r,21s)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1⁴,⁸.0¹⁶,²⁰]henicosa-1(19),16(20),17-trien-11-yl]acetic acid (NP0297782)

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Record Information

Version

1.0

Created at

2022-09-10 08:26:31 UTC

Updated at

2022-09-10 08:26:31 UTC

NP-MRD ID

NP0297782

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(4r,5s,7r,8r,11s,12s,13r,21s)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1⁴,⁸.0¹⁶,²⁰]henicosa-1(19),16(20),17-trien-11-yl]acetic acid

Description

Chebulinic acid, also known as chebulinate, belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. [(4r,5s,7r,8r,11s,12s,13r,21s)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1⁴,⁸.0¹⁶,²⁰]henicosa-1(19),16(20),17-trien-11-yl]acetic acid is found in Terminalia chebula. Based on a literature review very few articles have been published on Chebulinic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102210262D          

 68 74  0  0  1  0            999 V2000
    5.6658    2.3580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8617    2.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6191    1.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1807    0.7809    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4233    1.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3241    2.3884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2274    1.7536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7891    1.1493    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5613    0.2757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.7570    0.4592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3916    0.0380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0372   -1.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.4433    2.9992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2617    2.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7256    1.5134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4389    2.1349    0.0000 C   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
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
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  9 10  1  0  0  0  0
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  9 55  1  0  0  0  0
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M  END

     RDKit          3D

100106  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652309102210262D          

 68 74  0  0  1  0            999 V2000
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   11.2303   -3.1742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0758    0.5278    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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 35 34  1  1  0  0  0
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 66 68  2  0  0  0  0
 60 68  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0297782

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@H]2[C@H](CC(O)=O)C(=O)O[C@@H]3[C@@H](COC(=O)C4=CC(O)=C(O)C(O)=C4)O[C@@H](OC(=O)C4=CC(O)=C(O)C(O)=C4)[C@H](OC(=O)C4=CC(O)=C(O)C(OC1=O)=C24)[C@H]3OC(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49,50)/t14-,22+,24-,30+,31+,33-,34+,41-/m0/s1

> <INCHI_KEY>
YGVHOSGNOYKRIH-AVXZFDTDSA-N

> <FORMULA>
C41H32O27

> <MOLECULAR_WEIGHT>
956.68

> <EXACT_MASS>
956.11309577

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
84.61675886941144

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(4R,5S,7R,8R,11S,12S,13R,21S)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1^{4,8}.0^{16,20}]henicosa-1(19),16(20),17-trien-11-yl]acetic acid

> <JCHEM_LOGP>
3.022383389999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.559118092381712

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.158926682111319

> <JCHEM_PKA_STRONGEST_BASIC>
-4.7814753972837964

> <JCHEM_POLAR_SURFACE_AREA>
447.0900000000001

> <JCHEM_REFRACTIVITY>
210.9775

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(4R,5S,7R,8R,11S,12S,13R,21S)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1^{4,8}.0^{16,20}]henicosa-1(19),16(20),17-trien-11-yl]acetic acid

> <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  O   UNK     0      10.576   4.402   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.075   4.058   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.027   5.186   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       8.622   2.586   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.671   1.458   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.123   2.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       9.938   4.458   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      11.625   3.273   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.673   2.145   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.248   0.515   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.746   0.857   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.699  -0.272   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.198   0.071   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      10.153  -1.743   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.269  -2.290   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.108  -3.557   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      13.610  -3.900   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      11.061  -4.686   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.515  -6.158   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.560  -4.344   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.512  -5.473   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.106  -2.872   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.896  -0.882   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.768  -1.931   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.423  -1.182   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.055  -0.474   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.765  -1.486   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.312  -2.958   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.811  -3.302   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.358  -4.774   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.763  -2.174   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.262  -2.518   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.216  -0.702   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.717  -0.358   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.170   1.114   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.121   2.242   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       7.574   3.714   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       5.620   1.898   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       4.572   3.026   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       5.167   0.426   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      14.405  -0.402   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      15.414  -1.565   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      16.926  -1.272   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      17.429   0.183   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      17.935  -2.435   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      19.447  -2.143   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      20.457  -3.306   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      21.969  -3.014   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      19.954  -4.762   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      20.963  -5.925   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      18.442  -5.054   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      17.939  -6.510   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      17.433  -3.891   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      15.075   0.985   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      14.209   2.259   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      14.879   3.645   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      16.414   3.759   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      17.084   5.145   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      16.218   6.419   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      18.620   5.259   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      19.290   6.645   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      20.826   6.759   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      21.495   8.145   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      21.692   5.485   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      23.227   5.599   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      21.022   4.099   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      21.888   2.825   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      19.486   3.985   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   55                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   14                                                       
CONECT   23   10   24   41                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   40                                                  
CONECT   34   33   27   35                                                  
CONECT   35   34    5   36                                                  
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   33                                                       
CONECT   41   23   42   54                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46   53                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   45                                                       
CONECT   54   41   55                                                       
CONECT   55   54    9   56                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   61   68                                                  
CONECT   61   60   62                                                       
CONECT   62   61   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62   65   66                                                  
CONECT   65   64                                                            
CONECT   66   64   67   68                                                  
CONECT   67   66                                                            
CONECT   68   66   60                                                       
MASTER        0    0    0    0    0    0    0    0   68    0  148    0
END

View in JSmol

Synonyms

Value	Source
Chebulinate	Generator

Chemical Formula

C₄₁H₃₂O₂₇

Average Mass

956.6800 Da

Monoisotopic Mass

956.11310 Da

IUPAC Name

2-[(4R,5S,7R,8R,11S,12S,13R,21S)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1^{4,8}.0^{16,20}]henicosa-1(19),16(20),17-trien-11-yl]acetic acid

Traditional Name

[(4R,5S,7R,8R,11S,12S,13R,21S)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1^{4,8}.0^{16,20}]henicosa-1(19),16(20),17-trien-11-yl]acetic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@H]2[C@H](CC(O)=O)C(=O)O[C@@H]3[C@@H](COC(=O)C4=CC(O)=C(O)C(O)=C4)O[C@@H](OC(=O)C4=CC(O)=C(O)C(O)=C4)[C@H](OC(=O)C4=CC(O)=C(O)C(OC1=O)=C24)[C@H]3OC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C41H32O27/c42-15-1-10(2-16(43)26(15)51)35(56)62-9-22-31-33(66-36(57)11-3-17(44)27(52)18(45)4-11)34(41(63-22)68-37(58)12-5-19(46)28(53)20(47)6-12)67-38(59)13-7-21(48)29(54)32-25(13)24(30(55)40(61)65-32)14(8-23(49)50)39(60)64-31/h1-7,14,22,24,30-31,33-34,41-48,51-55H,8-9H2,(H,49,50)/t14-,22+,24-,30+,31+,33-,34+,41-/m0/s1

InChI Key

YGVHOSGNOYKRIH-AVXZFDTDSA-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
Terminalia chebula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Saccharolipid
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
3,4-dihydrocoumarin
Dihydroxybenzoic acid
Benzoate ester
Chromane
Benzopyran
1-benzopyran
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Benzoyl
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Oxane
Benzenoid
Monosaccharide
Carboxylic acid ester
Secondary alcohol
Lactone
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Acetal
Polyol
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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	3.02	ChemAxon
pKa (Strongest Acidic)	3.16	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	447.09 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	210.98 m³·mol⁻¹	ChemAxon
Polarizability	84.62 Å³	ChemAxon
Number of Rings	7	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

C00002912

Chemspider ID

58172610

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chebulinic acid

METLIN ID

Not Available

PubChem Compound

99937814

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(4r,5s,7r,8r,11s,12s,13r,21s)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1⁴,⁸.0¹⁶,²⁰]henicosa-1(19),16(20),17-trien-11-yl]acetic acid (NP0297782)

MOL for NP0297782 ([(4r,5s,7r,8r,11s,12s,13r,21s)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1⁴,⁸.0¹⁶,²⁰]henicosa-1(19),16(20),17-trien-11-yl]acetic acid)

3D MOL for NP0297782 ([(4r,5s,7r,8r,11s,12s,13r,21s)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1⁴,⁸.0¹⁶,²⁰]henicosa-1(19),16(20),17-trien-11-yl]acetic acid)

3D SDF for NP0297782 ([(4r,5s,7r,8r,11s,12s,13r,21s)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1⁴,⁸.0¹⁶,²⁰]henicosa-1(19),16(20),17-trien-11-yl]acetic acid)

3D-SDF for NP0297782 ([(4r,5s,7r,8r,11s,12s,13r,21s)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1⁴,⁸.0¹⁶,²⁰]henicosa-1(19),16(20),17-trien-11-yl]acetic acid)

PDB for NP0297782 ([(4r,5s,7r,8r,11s,12s,13r,21s)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1⁴,⁸.0¹⁶,²⁰]henicosa-1(19),16(20),17-trien-11-yl]acetic acid)

3D PDB for NP0297782 ([(4r,5s,7r,8r,11s,12s,13r,21s)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1⁴,⁸.0¹⁶,²⁰]henicosa-1(19),16(20),17-trien-11-yl]acetic acid)

SMILES for NP0297782 ([(4r,5s,7r,8r,11s,12s,13r,21s)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1⁴,⁸.0¹⁶,²⁰]henicosa-1(19),16(20),17-trien-11-yl]acetic acid)

INCHI for NP0297782 ([(4r,5s,7r,8r,11s,12s,13r,21s)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1⁴,⁸.0¹⁶,²⁰]henicosa-1(19),16(20),17-trien-11-yl]acetic acid)

Structure for NP0297782 ([(4r,5s,7r,8r,11s,12s,13r,21s)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1⁴,⁸.0¹⁶,²⁰]henicosa-1(19),16(20),17-trien-11-yl]acetic acid)

3D Structure for NP0297782 ([(4r,5s,7r,8r,11s,12s,13r,21s)-13,17,18-trihydroxy-2,10,14-trioxo-5,21-bis(3,4,5-trihydroxybenzoyloxy)-7-[(3,4,5-trihydroxybenzoyloxy)methyl]-3,6,9,15-tetraoxatetracyclo[10.7.1.1⁴,⁸.0¹⁶,²⁰]henicosa-1(19),16(20),17-trien-11-yl]acetic acid)