NP-MRD: Showing NP-Card for (8s,9s,10s,11r)-3,9,16-trihydroxy-4,5,14,15-tetramethoxy-9,10-dimethyl-11-{[(2z)-2-methylbut-2-enoyl]oxy}tricyclo[10.4.0.0²,⁷]hexadeca-1(16),2(7),3,5,12,14-hexaen-8-yl benzoate (NP0265781)

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Record Information

Version

1.0

Created at

2022-09-08 09:53:02 UTC

Updated at

2022-09-08 09:53:02 UTC

NP-MRD ID

NP0265781

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(8s,9s,10s,11r)-3,9,16-trihydroxy-4,5,14,15-tetramethoxy-9,10-dimethyl-11-{[(2z)-2-methylbut-2-enoyl]oxy}tricyclo[10.4.0.0²,⁷]hexadeca-1(16),2(7),3,5,12,14-hexaen-8-yl benzoate

Description

Renchangianin B 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) 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. It was first documented in 2016 (PMID: 30156799). Based on a literature review a significant number of articles have been published on Renchangianin B (PMID: 36104165) (PMID: 36104164) (PMID: 36104163) (PMID: 36104162).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082211532D          

 45 48  0  0  1  0            999 V2000
    4.2864    6.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9409    6.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8332    5.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4877    4.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0710    4.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4165    5.3806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9633    4.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2011    3.7447    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2011    2.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9980    2.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2115    1.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0084    1.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5918    2.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6282    1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8417    0.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6386    0.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8313    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2479    0.9561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6178    2.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7928    2.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2094    2.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9335    5.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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 41 42  1  6  0  0  0
 41 43  1  1  0  0  0
 41 44  1  0  0  0  0
  8 44  1  0  0  0  0
 44 45  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309082211532D          

 45 48  0  0  1  0            999 V2000
    4.2864    6.5143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9633    4.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2011    3.7447    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.9980    2.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6386    0.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8313    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2479    0.9561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6178    2.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7928    2.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2094    2.9197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1990    1.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5979    1.6958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813    2.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7823    1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5688    0.5291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2281    0.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9538    0.8044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2094    3.7447    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4472    4.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3395    4.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9940    5.3806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4227    5.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0772    4.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8394    5.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9471    5.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2926    6.3277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5304    6.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7928    4.3281    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0783    4.7406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0063    5.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6178    4.3281    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9335    5.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  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
 11 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  2  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  0  0  0  0
 21 31  1  0  0  0  0
 31 32  1  6  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 35 40  1  0  0  0  0
 31 41  1  0  0  0  0
 41 42  1  6  0  0  0
 41 43  1  1  0  0  0
 41 44  1  0  0  0  0
  8 44  1  0  0  0  0
 44 45  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0265781

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C(O)=C1OC)C1=C(O)C(OC)=C(OC)C=C1[C@H](OC(=O)C(\C)=C/C)[C@H](C)[C@](C)(O)[C@H]2OC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C34H38O11/c1-9-17(2)32(37)44-28-18(3)34(4,39)31(45-33(38)19-13-11-10-12-14-19)21-16-23(41-6)30(43-8)27(36)25(21)24-20(28)15-22(40-5)29(42-7)26(24)35/h9-16,18,28,31,35-36,39H,1-8H3/b17-9-/t18-,28+,31-,34-/m0/s1

> <INCHI_KEY>
FGACFCPIJZFIEZ-NLBSZNOBSA-N

> <FORMULA>
C34H38O11

> <MOLECULAR_WEIGHT>
622.667

> <EXACT_MASS>
622.241412044

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
64.95448054708682

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8S,9S,10S,11R)-3,9,16-trihydroxy-4,5,14,15-tetramethoxy-9,10-dimethyl-11-{[(2Z)-2-methylbut-2-enoyl]oxy}tricyclo[10.4.0.0^{2,7}]hexadeca-1(16),2(7),3,5,12,14-hexaen-8-yl benzoate

> <JCHEM_LOGP>
5.693727241999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.889116937942559

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.046601725562196

> <JCHEM_PKA_STRONGEST_BASIC>
-3.416361654486084

> <JCHEM_POLAR_SURFACE_AREA>
150.21

> <JCHEM_REFRACTIVITY>
165.54629999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(8S,9S,10S,11R)-3,9,16-trihydroxy-4,5,14,15-tetramethoxy-9,10-dimethyl-11-{[(2Z)-2-methylbut-2-enoyl]oxy}tricyclo[10.4.0.0^{2,7}]hexadeca-1(16),2(7),3,5,12,14-hexaen-8-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       8.001  12.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.223  11.222   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.022   9.696   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.244   8.758   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.599   9.106   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.377  10.044   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.398   7.579   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.975   6.990   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.975   5.450   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.463   5.052   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.862   3.564   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.349   3.165   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.438   4.254   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.773   2.475   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.171   0.988   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.659   0.589   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.285   2.874   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.196   1.785   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.886   4.361   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.346   4.361   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.258   5.450   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.770   5.052   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.371   3.564   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.116   3.165   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.205   4.254   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.460   2.475   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.062   0.988   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.426   0.589   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.948   2.874   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.647   1.502   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.258   6.990   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.835   7.579   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.634   9.106   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.856  10.044   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.789   9.696   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.011   8.758   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.434   9.347   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -3.635  10.874   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -2.413  11.812   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -0.990  11.222   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.346   8.079   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.013   8.849   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       3.745   9.567   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       4.886   8.079   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       5.476   9.502   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   44                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    9   20                                                  
CONECT   20   19   21   29                                                  
CONECT   21   20   22   31                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   26   20   30                                                  
CONECT   30   29                                                            
CONECT   31   21   32   41                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   35                                                       
CONECT   41   31   42   43   44                                             
CONECT   42   41                                                            
CONECT   43   41                                                            
CONECT   44   41    8   45                                                  
CONECT   45   44                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₃₈O₁₁

Average Mass

622.6670 Da

Monoisotopic Mass

622.24141 Da

IUPAC Name

(8S,9S,10S,11R)-3,9,16-trihydroxy-4,5,14,15-tetramethoxy-9,10-dimethyl-11-{[(2Z)-2-methylbut-2-enoyl]oxy}tricyclo[10.4.0.0^{2,7}]hexadeca-1(16),2(7),3,5,12,14-hexaen-8-yl benzoate

Traditional Name

(8S,9S,10S,11R)-3,9,16-trihydroxy-4,5,14,15-tetramethoxy-9,10-dimethyl-11-{[(2Z)-2-methylbut-2-enoyl]oxy}tricyclo[10.4.0.0^{2,7}]hexadeca-1(16),2(7),3,5,12,14-hexaen-8-yl benzoate

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C(O)=C1OC)C1=C(O)C(OC)=C(OC)C=C1[C@H](OC(=O)C(\C)=C/C)[C@H](C)[C@](C)(O)[C@H]2OC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C34H38O11/c1-9-17(2)32(37)44-28-18(3)34(4,39)31(45-33(38)19-13-11-10-12-14-19)21-16-23(41-6)30(43-8)27(36)25(21)24-20(28)15-22(40-5)29(42-7)26(24)35/h9-16,18,28,31,35-36,39H,1-8H3/b17-9-/t18-,28+,31-,34-/m0/s1

InChI Key

FGACFCPIJZFIEZ-NLBSZNOBSA-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

Not Available

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) 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
Dibenzocyclooctane lignan
Benzoate ester
Benzoic acid or derivatives
Anisole
Benzoyl
Phenol ether
Phenol
Fatty acid ester
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Enoate ester
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	5.69	ChemAxon
pKa (Strongest Acidic)	9.05	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	150.21 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	165.55 m³·mol⁻¹	ChemAxon
Polarizability	64.95 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102073771

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bamat NA, Orians CM, Abbasi S, Morley CJ, Ross Russell R, Panitch HB, Handley SC, Foglia EE, Posencheg MA, Kirpalani H: Use of ventilation/perfusion mismatch to guide individualised CPAP level selection in preterm infants: a feasibility trial. Arch Dis Child Fetal Neonatal Ed. 2022 Sep 14. pii: archdischild-2022-324474. doi: 10.1136/archdischild-2022-324474. [PubMed:36104165 ]
Kopel D, Gottschalk CH: The Epidemiology of Primary Headache Disorders. Semin Neurol. 2022 Sep 14. doi: 10.1055/a-1942-6823. [PubMed:36104164 ]
Cleary NM, O'Gorman A: Hyaluronidase for localised infusion site reaction during continuous subcutaneous infusion. BMJ Support Palliat Care. 2022 Sep 14. pii: spcare-2022-003909. doi: 10.1136/spcare-2022-003909. [PubMed:36104163 ]
Hayes J, Waldron D, Levins KJ, Gaffney L, Azhar M, Beatty S, Mannion E: Methadone prescribed as an analgesic by a specialist palliative medicine team in an acute hospital inpatient setting: retrospective study. BMJ Support Palliat Care. 2022 Sep 14. pii: spcare-2022-003586. doi: 10.1136/spcare-2022-003586. [PubMed:36104162 ]
Guo YJ, Gao SM, Zhang BG, Liu HT: [Chemical Constituents from Stems of Kadsura longipedunculata]. Zhong Yao Cai. 2016 Jun;39(6):1287-90. [PubMed:30156799 ]
LOTUS database [Link]

Showing NP-Card for (8s,9s,10s,11r)-3,9,16-trihydroxy-4,5,14,15-tetramethoxy-9,10-dimethyl-11-{[(2z)-2-methylbut-2-enoyl]oxy}tricyclo[10.4.0.0²,⁷]hexadeca-1(16),2(7),3,5,12,14-hexaen-8-yl benzoate (NP0265781)

MOL for NP0265781 ((8s,9s,10s,11r)-3,9,16-trihydroxy-4,5,14,15-tetramethoxy-9,10-dimethyl-11-{[(2z)-2-methylbut-2-enoyl]oxy}tricyclo[10.4.0.0²,⁷]hexadeca-1(16),2(7),3,5,12,14-hexaen-8-yl benzoate)

3D MOL for NP0265781 ((8s,9s,10s,11r)-3,9,16-trihydroxy-4,5,14,15-tetramethoxy-9,10-dimethyl-11-{[(2z)-2-methylbut-2-enoyl]oxy}tricyclo[10.4.0.0²,⁷]hexadeca-1(16),2(7),3,5,12,14-hexaen-8-yl benzoate)

3D SDF for NP0265781 ((8s,9s,10s,11r)-3,9,16-trihydroxy-4,5,14,15-tetramethoxy-9,10-dimethyl-11-{[(2z)-2-methylbut-2-enoyl]oxy}tricyclo[10.4.0.0²,⁷]hexadeca-1(16),2(7),3,5,12,14-hexaen-8-yl benzoate)

3D-SDF for NP0265781 ((8s,9s,10s,11r)-3,9,16-trihydroxy-4,5,14,15-tetramethoxy-9,10-dimethyl-11-{[(2z)-2-methylbut-2-enoyl]oxy}tricyclo[10.4.0.0²,⁷]hexadeca-1(16),2(7),3,5,12,14-hexaen-8-yl benzoate)

PDB for NP0265781 ((8s,9s,10s,11r)-3,9,16-trihydroxy-4,5,14,15-tetramethoxy-9,10-dimethyl-11-{[(2z)-2-methylbut-2-enoyl]oxy}tricyclo[10.4.0.0²,⁷]hexadeca-1(16),2(7),3,5,12,14-hexaen-8-yl benzoate)

3D PDB for NP0265781 ((8s,9s,10s,11r)-3,9,16-trihydroxy-4,5,14,15-tetramethoxy-9,10-dimethyl-11-{[(2z)-2-methylbut-2-enoyl]oxy}tricyclo[10.4.0.0²,⁷]hexadeca-1(16),2(7),3,5,12,14-hexaen-8-yl benzoate)

SMILES for NP0265781 ((8s,9s,10s,11r)-3,9,16-trihydroxy-4,5,14,15-tetramethoxy-9,10-dimethyl-11-{[(2z)-2-methylbut-2-enoyl]oxy}tricyclo[10.4.0.0²,⁷]hexadeca-1(16),2(7),3,5,12,14-hexaen-8-yl benzoate)

INCHI for NP0265781 ((8s,9s,10s,11r)-3,9,16-trihydroxy-4,5,14,15-tetramethoxy-9,10-dimethyl-11-{[(2z)-2-methylbut-2-enoyl]oxy}tricyclo[10.4.0.0²,⁷]hexadeca-1(16),2(7),3,5,12,14-hexaen-8-yl benzoate)

Structure for NP0265781 ((8s,9s,10s,11r)-3,9,16-trihydroxy-4,5,14,15-tetramethoxy-9,10-dimethyl-11-{[(2z)-2-methylbut-2-enoyl]oxy}tricyclo[10.4.0.0²,⁷]hexadeca-1(16),2(7),3,5,12,14-hexaen-8-yl benzoate)

3D Structure for NP0265781 ((8s,9s,10s,11r)-3,9,16-trihydroxy-4,5,14,15-tetramethoxy-9,10-dimethyl-11-{[(2z)-2-methylbut-2-enoyl]oxy}tricyclo[10.4.0.0²,⁷]hexadeca-1(16),2(7),3,5,12,14-hexaen-8-yl benzoate)