NP-MRD: Showing NP-Card for [(5s,8r,11s,12s,13r,21r)-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 (NP0325568)

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Record Information

Version

1.0

Created at

2022-09-12 06:24:49 UTC

Updated at

2022-09-12 06:24:50 UTC

NP-MRD ID

NP0325568

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(5s,8r,11s,12s,13r,21r)-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. [(5s,8r,11s,12s,13r,21r)-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 Lumnitzera racemosa, Terminalia chebula and Terminalia citrina. It was first documented in 2022 (PMID: 36051270). Based on a literature review a significant number of articles have been published on Chebulinic acid (PMID: 35830757) (PMID: 35967775) (PMID: 35729191) (PMID: 35630681).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122208242D          

 68 74  0  0  1  0            999 V2000
    3.7981    2.3442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5523    2.0100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2189    2.4961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    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
    4.8617    2.1738    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  2  0  0  0  0  0  0  0  0  0
    7.6118    1.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9706    1.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7934    2.0136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1522    2.7564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6883    3.4386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9750    2.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3338    3.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1566    3.6207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5154    4.3636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6205    2.9385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   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
    8.0758    0.5278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7169   -0.2151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2576   -0.8382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0676   -0.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.7689   -1.6146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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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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    6.9087   -0.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6488   -1.7689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2830   -1.3488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3298   -0.3760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1340   -0.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3765    0.5967    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8149    1.2010    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0575    1.9896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0107    1.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491    1.6212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.6895   -1.1475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1644   -1.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8176   -2.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2925   -3.2453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9960   -2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6492   -3.3933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5210   -1.9701    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
  6  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
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 15 23  1  0  0  0  0
 10 24  1  0  0  0  0
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  5 50  1  0  0  0  0
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  9 56  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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 37 29  1  0
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 68100  1  0
M  END


  Mrv1652309122208242D          

 68 74  0  0  1  0            999 V2000
    3.7981    2.3442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1340   -0.1918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3765    0.5967    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8149    1.2010    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0575    1.9896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0107    1.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4491    1.6212    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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  9  8  1  6  0  0  0
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  5 50  1  0  0  0  0
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  9 56  1  0  0  0  0
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 58 59  2  0  0  0  0
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 64 66  1  0  0  0  0
 66 67  1  0  0  0  0
 66 68  2  0  0  0  0
 60 68  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325568

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@H]2[C@H](CC(O)=O)C(=O)O[C@@H]3C(COC(=O)C4=CC(O)=C(O)C(O)=C4)O[C@@H](OC(=O)C4=CC(O)=C(O)C(O)=C4)C(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-JYHBNSAESA-N

> <FORMULA>
C41H32O27

> <MOLECULAR_WEIGHT>
956.68

> <EXACT_MASS>
956.11309577

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
86.00354737587108

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
13

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(5S,8R,11S,12S,13R,21R)-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>
210.97750000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(5S,8R,11S,12S,13R,21R)-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                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0       7.090   4.376   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.498   3.752   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.742   4.659   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       9.075   4.058   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      14.209   2.259   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.879   3.645   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      16.414   3.759   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      17.084   5.145   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      16.218   6.419   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      18.620   5.259   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.290   6.645   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.826   6.759   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      21.495   8.145   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      21.692   5.485   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      23.227   5.599   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      21.022   4.099   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      21.888   2.825   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      19.486   3.985   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      15.075   0.985   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      14.405  -0.402   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      15.414  -1.565   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      16.926  -1.272   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      17.429   0.183   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      17.935  -2.435   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      19.447  -2.143   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      20.457  -3.306   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      21.969  -3.014   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      19.954  -4.762   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      20.963  -5.925   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      18.442  -5.054   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      17.939  -6.510   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      17.433  -3.891   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      12.896  -0.882   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      11.768  -1.931   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      10.524  -1.374   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      10.095   0.032   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       8.867  -1.679   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       8.312  -2.958   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       6.811  -3.302   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       6.358  -4.774   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       5.763  -2.174   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       4.262  -2.518   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       6.216  -0.702   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       7.717  -0.358   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       8.170   1.114   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       7.121   2.242   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       7.574   3.714   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       5.620   1.898   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       4.572   3.026   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       5.167   0.426   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      12.248   0.515   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      10.714   0.376   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      10.067  -1.021   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       8.533  -1.159   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      10.953  -2.280   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      12.487  -2.142   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      13.374  -3.401   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      14.907  -3.263   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      12.726  -4.799   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      13.613  -6.058   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      11.192  -4.937   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      10.545  -6.334   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      10.306  -3.677   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   50                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   56                                                  
CONECT   10    9   11   24                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   15                                                       
CONECT   24   10   25                                                       
CONECT   25   24   26   38                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   37                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   29                                                       
CONECT   38   25   39   56                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   49                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   55                                                  
CONECT   49   48   42   50                                                  
CONECT   50   49    5   51                                                  
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   48                                                       
CONECT   56   38    9   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

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@H]2[C@H](CC(O)=O)C(=O)O[C@@H]3C(COC(=O)C4=CC(O)=C(O)C(O)=C4)O[C@@H](OC(=O)C4=CC(O)=C(O)C(O)=C4)C(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-JYHBNSAESA-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
Lumnitzera racemosa	LOTUS Database	35616633
Terminalia chebula	LOTUS Database	35616633
Terminalia citrina	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
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Dihydroxybenzoic acid
3,4-dihydrocoumarin
1-benzopyran
Benzopyran
Chromane
Benzoate ester
Pyrogallol derivative
Benzoic acid or derivatives
Benzenetriol
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chebulinic acid

METLIN ID

Not Available

PubChem Compound

138857791

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hassan Bulbul MR, Uddin Chowdhury MN, Naima TA, Sami SA, Imtiaj MS, Huda N, Uddin MG: A comprehensive review on the diverse pharmacological perspectives of Terminalia chebula Retz. Heliyon. 2022 Aug 14;8(8):e10220. doi: 10.1016/j.heliyon.2022.e10220. eCollection 2022 Aug. [PubMed:36051270 ]
Kim HJ, Song HK, Park SH, Jang S, Park KS, Song KH, Lee SK, Kim T: Terminalia chebula Retz. extract ameliorates the symptoms of atopic dermatitis by regulating anti-inflammatory factors in vivo and suppressing STAT1/3 and NF-kB signaling in vitro. Phytomedicine. 2022 Sep;104:154318. doi: 10.1016/j.phymed.2022.154318. Epub 2022 Jul 4. [PubMed:35830757 ]
Phan ADT, Zhang J, Seididamyeh M, Srivarathan S, Netzel ME, Sivakumar D, Sultanbawa Y: Hydrolysable tannins, physicochemical properties, and antioxidant property of wild-harvested Terminalia ferdinandiana (exell) fruit at different maturity stages. Front Nutr. 2022 Jul 29;9:961679. doi: 10.3389/fnut.2022.961679. eCollection 2022. [PubMed:35967775 ]
Thomas N, Patil P, Sharma A, Kumar S, Singh VK, Alagarasu K, Parashar D, Tapryal S: Studies on the antiviral activity of chebulinic acid against dengue and chikungunya viruses and in silico investigation of its mechanism of inhibition. Sci Rep. 2022 Jun 21;12(1):10397. doi: 10.1038/s41598-022-13923-6. [PubMed:35729191 ]
Virtanen V, Green RJ, Karonen M: Interactions between Hydrolysable Tannins and Lipid Vesicles from Escherichia coli with Isothermal Titration Calorimetry. Molecules. 2022 May 17;27(10):3204. doi: 10.3390/molecules27103204. [PubMed:35630681 ]
LOTUS database [Link]

Showing NP-Card for [(5s,8r,11s,12s,13r,21r)-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 (NP0325568)

MOL for NP0325568 ([(5s,8r,11s,12s,13r,21r)-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 NP0325568 ([(5s,8r,11s,12s,13r,21r)-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 NP0325568 ([(5s,8r,11s,12s,13r,21r)-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 NP0325568 ([(5s,8r,11s,12s,13r,21r)-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 NP0325568 ([(5s,8r,11s,12s,13r,21r)-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 NP0325568 ([(5s,8r,11s,12s,13r,21r)-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 NP0325568 ([(5s,8r,11s,12s,13r,21r)-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 NP0325568 ([(5s,8r,11s,12s,13r,21r)-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 NP0325568 ([(5s,8r,11s,12s,13r,21r)-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 NP0325568 ([(5s,8r,11s,12s,13r,21r)-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)