Np mrd loader

Showing NP-Card for Isoterchebin (NP0051677)

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Record Information
Version2.0
Created at2022-04-27 22:57:20 UTC
Updated at2022-04-27 22:57:20 UTC
NP-MRD IDNP0051677
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsoterchebin
Description(1S,8R,10S,11R,12S,13R,22R)-1,18,19,23,23-pentahydroxy-2,5,15-trioxo-10,11-bis(3,4,5-trihydroxybenzoyloxy)-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]Tetracosa-3,16,18,20-tetraen-12-yl 3,4,5-trihydroxybenzoate 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. Isoterchebin is found in Cornus officinalis , Cytinus hypocistis and Trapa japonica . Based on a literature review very few articles have been published on (1S,8R,10S,11R,12S,13R,22R)-1,18,19,23,23-pentahydroxy-2,5,15-trioxo-10,11-bis(3,4,5-trihydroxybenzoyloxy)-6,9,14,24-tetraoxapentacyclo[18.3.1.0⁴,²².0⁸,¹³.0¹⁶,²¹]Tetracosa-3,16,18,20-tetraen-12-yl 3,4,5-trihydroxybenzoate.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0051677 (Isoterchebin)


  Mrv1652304282200572D          

 68 75  0  0  1  0            999 V2000
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M  END
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3D MOL for NP0051677 (Isoterchebin)

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3D SDF for NP0051677 (Isoterchebin)

  Mrv1652304282200572D          

 68 75  0  0  1  0            999 V2000
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 46 48  1  0  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  2  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 48 53  1  0  0  0  0
 52 54  1  0  0  0  0
 51 55  1  0  0  0  0
 50 56  1  0  0  0  0
  2 57  1  1  0  0  0
 57 58  1  0  0  0  0
 58 59  2  0  0  0  0
 58 60  1  0  0  0  0
 60 61  2  0  0  0  0
 61 62  1  0  0  0  0
 62 63  2  0  0  0  0
 63 64  1  0  0  0  0
 64 65  2  0  0  0  0
 60 65  1  0  0  0  0
 64 66  1  0  0  0  0
 63 67  1  0  0  0  0
 62 68  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051677

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(=CC(O)=C1O)C(=O)O[C@@H]1O[C@@H]2COC(=O)C3=CC(=O)[C@@]4(O)OC5=C([C@H]3C4(O)O)C(=CC(O)=C5O)C(=O)O[C@H]2[C@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C41H30O27/c42-15-1-10(2-16(43)26(15)50)34(54)65-32-30-22(9-62-37(57)14-8-23(49)41(61)40(59,60)25(14)24-13(38(58)64-30)7-21(48)29(53)31(24)68-41)63-39(67-36(56)12-5-19(46)28(52)20(47)6-12)33(32)66-35(55)11-3-17(44)27(51)18(45)4-11/h1-8,22,25,30,32-33,39,42-48,50-53,59-61H,9H2/t22-,25+,30-,32+,33-,39+,41-/m1/s1

> <INCHI_KEY>
QFJVFTCFAZSXCY-ZZFVZTRASA-N

> <FORMULA>
C41H30O27

> <MOLECULAR_WEIGHT>
954.664

> <EXACT_MASS>
954.097445706

> <JCHEM_ACCEPTOR_COUNT>
22

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
49.86896777557703

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
14

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,8R,10S,11R,12S,13R,22R)-1,18,19,23,23-pentahydroxy-2,5,15-trioxo-11,12-bis(3,4,5-trihydroxybenzoyloxy)-6,9,14,24-tetraoxapentacyclo[18.3.1.0^{4,22}.0^{8,13}.0^{16,21}]tetracosa-3,16,18,20-tetraen-10-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
2.9272553809999993

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.653149219438976

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.684885524636398

> <JCHEM_PKA_STRONGEST_BASIC>
-5.549137588051679

> <JCHEM_POLAR_SURFACE_AREA>
450.2500000000001

> <JCHEM_REFRACTIVITY>
211.47810000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,8R,10S,11R,12S,13R,22R)-1,18,19,23,23-pentahydroxy-2,5,15-trioxo-11,12-bis(3,4,5-trihydroxybenzoyloxy)-6,9,14,24-tetraoxapentacyclo[18.3.1.0^{4,22}.0^{8,13}.0^{16,21}]tetracosa-3,16,18,20-tetraen-10-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0051677 (Isoterchebin)
Download
PDB for NP0051677 (Isoterchebin)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.124  -1.993   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.509  -2.666   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.785  -1.804   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.675  -0.267   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.290   0.406   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.015  -0.457   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.869   0.972   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.178   0.828   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.228  -0.151   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.801   0.962   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.822  -2.031   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.621  -0.262   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.030   0.568   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.459   2.219   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.398  -0.426   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.806  -1.753   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.288  -2.877   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.978  -3.573   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.228  -2.606   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.833  -3.209   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.186  -4.712   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.877  -5.649   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.613  -5.240   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.503  -4.506   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.370  -5.688   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.173  -3.674   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       8.806  -5.295   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       7.688  -1.802   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       4.830  -1.061   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.303  -1.216   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.386  -3.111   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       3.907   1.453   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       9.336   1.259   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.074   2.684   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       9.017   3.869   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.706   2.923   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      12.044   4.426   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.514   4.884   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      14.646   3.840   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      14.308   2.338   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      12.838   1.879   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      15.440   1.294   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      16.116   4.299   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      13.852   6.387   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      10.377  -1.928   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0      11.937  -1.649   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      12.366  -0.138   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      13.272  -2.418   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      14.676  -1.784   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      15.926  -2.683   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      15.773  -4.215   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      14.370  -4.849   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      13.119  -3.950   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      14.217  -6.381   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      17.024  -5.114   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      17.330  -2.049   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       8.244  -4.213   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0       7.716  -5.897   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       6.496  -6.983   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       8.792  -6.978   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      10.313  -6.734   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      11.285  -7.928   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      10.736  -9.367   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0       9.215  -9.612   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       8.244  -8.417   0.000  0.00  0.00           C+0
HETATM   66  O   UNK     0       8.667 -11.050   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      11.708 -10.562   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0      12.805  -7.684   0.000  0.00  0.00           O+0
CONECT    1    2    6   26                                                  
CONECT    2    1    3   57                                                  
CONECT    3    2    4   45                                                  
CONECT    4    3    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   29   32                                             
CONECT   16   15   17   30   31                                             
CONECT   17   16   11   18                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20   29                                                  
CONECT   20   19   21   28                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    1                                                       
CONECT   27   21                                                            
CONECT   28   20                                                            
CONECT   29   19   15                                                       
CONECT   30   16                                                            
CONECT   31   16                                                            
CONECT   32   15                                                            
CONECT   33    4   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39   44                                                  
CONECT   39   38   40   43                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40   36                                                       
CONECT   42   40                                                            
CONECT   43   39                                                            
CONECT   44   38                                                            
CONECT   45    3   46                                                       
CONECT   46   45   47   48                                                  
CONECT   47   46                                                            
CONECT   48   46   49   53                                                  
CONECT   49   48   50                                                       
CONECT   50   49   51   56                                                  
CONECT   51   50   52   55                                                  
CONECT   52   51   53   54                                                  
CONECT   53   52   48                                                       
CONECT   54   52                                                            
CONECT   55   51                                                            
CONECT   56   50                                                            
CONECT   57    2   58                                                       
CONECT   58   57   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   61   65                                                  
CONECT   61   60   62                                                       
CONECT   62   61   63   68                                                  
CONECT   63   62   64   67                                                  
CONECT   64   63   65   66                                                  
CONECT   65   64   60                                                       
CONECT   66   64                                                            
CONECT   67   63                                                            
CONECT   68   62                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  150    0
END

Download
3D PDB for NP0051677 (Isoterchebin)
Download
SMILES for NP0051677 (Isoterchebin)
OC1=CC(=CC(O)=C1O)C(=O)O[C@@H]1O[C@@H]2COC(=O)C3=CC(=O)[C@@]4(O)OC5=C([C@H]3C4(O)O)C(=CC(O)=C5O)C(=O)O[C@H]2[C@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1
Download
INCHI for NP0051677 (Isoterchebin)
InChI=1S/C41H30O27/c42-15-1-10(2-16(43)26(15)50)34(54)65-32-30-22(9-62-37(57)14-8-23(49)41(61)40(59,60)25(14)24-13(38(58)64-30)7-21(48)29(53)31(24)68-41)63-39(67-36(56)12-5-19(46)28(52)20(47)6-12)33(32)66-35(55)11-3-17(44)27(51)18(45)4-11/h1-8,22,25,30,32-33,39,42-48,50-53,59-61H,9H2/t22-,25+,30-,32+,33-,39+,41-/m1/s1
Download
View in JSmol
Synonyms
ValueSource
(1S,8R,10S,11R,12S,13R,22R)-1,18,19,23,23-Pentahydroxy-2,5,15-trioxo-10,11-bis(3,4,5-trihydroxybenzoyloxy)-6,9,14,24-tetraoxapentacyclo[18.3.1.0,.0,.0,]tetracosa-3,16,18,20-tetraen-12-yl 3,4,5-trihydroxybenzoic acidGenerator
Chemical FormulaC41H30O27
Average Mass954.6640 Da
Monoisotopic Mass954.09745 Da
IUPAC Name(1S,8R,10S,11R,12S,13R,22R)-1,18,19,23,23-pentahydroxy-2,5,15-trioxo-11,12-bis(3,4,5-trihydroxybenzoyloxy)-6,9,14,24-tetraoxapentacyclo[18.3.1.0^{4,22}.0^{8,13}.0^{16,21}]tetracosa-3,16,18,20-tetraen-10-yl 3,4,5-trihydroxybenzoate
Traditional Name(1S,8R,10S,11R,12S,13R,22R)-1,18,19,23,23-pentahydroxy-2,5,15-trioxo-11,12-bis(3,4,5-trihydroxybenzoyloxy)-6,9,14,24-tetraoxapentacyclo[18.3.1.0^{4,22}.0^{8,13}.0^{16,21}]tetracosa-3,16,18,20-tetraen-10-yl 3,4,5-trihydroxybenzoate
CAS Registry NumberNot Available
SMILES
OC1=CC(=CC(O)=C1O)C(=O)O[C@@H]1O[C@@H]2COC(=O)C3=CC(=O)[C@@]4(O)OC5=C([C@H]3C4(O)O)C(=CC(O)=C5O)C(=O)O[C@H]2[C@H](OC(=O)C2=CC(O)=C(O)C(O)=C2)[C@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1
InChI Identifier
InChI=1S/C41H30O27/c42-15-1-10(2-16(43)26(15)50)34(54)65-32-30-22(9-62-37(57)14-8-23(49)41(61)40(59,60)25(14)24-13(38(58)64-30)7-21(48)29(53)31(24)68-41)63-39(67-36(56)12-5-19(46)28(52)20(47)6-12)33(32)66-35(55)11-3-17(44)27(51)18(45)4-11/h1-8,22,25,30,32-33,39,42-48,50-53,59-61H,9H2/t22-,25+,30-,32+,33-,39+,41-/m1/s1
InChI KeyQFJVFTCFAZSXCY-ZZFVZTRASA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Cornus officinalisPlant
Cytinus hypocistisPlant
Trapa japonicaPlant
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.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassTannins  
Sub ClassHydrolyzable tannins  
Direct ParentHydrolyzable tannins  
Alternative Parents
Substituents
  • Hydrolyzable tannin
    • 

  • Pentacarboxylic acid or derivatives
    • 

  • Galloyl ester
    • 

  • Gallic acid or derivatives
    • 

  • P-hydroxybenzoic acid alkyl ester
    • 

  • M-hydroxybenzoic acid ester
    • 

  • P-hydroxybenzoic acid ester
    • 

  • Dihydroxybenzoic acid
    • 

  • 1-benzopyran
    • 

  • Benzopyran
    • 

  • Chromane
    • 

  • Benzoate ester
    • 

  • Pyrogallol derivative
    • 

  • Benzoic acid or derivatives
    • 

  • Benzenetriol
    • 

  • Benzoyl
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Cyclohexenone
    • 

  • Phenol
    • 

  • Benzenoid
    • 

  • Oxane
    • 

  • Monosaccharide
    • 

  • Monocyclic benzene moiety
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Lactone
    • 

  • Ketone
    • 

  • Hemiacetal
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Carboxylic acid derivative
    • 

  • Carbonyl hydrate
    • 

  • Acetal
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.55ALOGPS
logP2.93ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)5.68ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area450.25 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity211.48 m³·mol⁻¹ChemAxon
Polarizability49.87 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162913656  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available