NP-MRD: Showing NP-Card for (-)-Ciwujianoside C3 (NP0074224)

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Record Information

Version

2.0

Created at

2022-04-28 19:23:16 UTC

Updated at

2022-04-28 19:23:16 UTC

NP-MRD ID

NP0074224

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Ciwujianoside C3

Description

Ciwujianoside C3 belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. (-)-Ciwujianoside C3 is found in Clematis chinensis, Cussonia arborea, Acanthopanax senticosus , Eleutherococcus senticosus Rupr.and Maxim. , Meryta denhamii, Meryta lanceolata and Anemone dahurica. (-)-Ciwujianoside C3 was first documented in 2016 (PMID: 27600484). Based on a literature review a small amount of articles have been published on ciwujianoside C3 (PMID: 33605281) (PMID: 31121888).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221232D          

 74 82  0  0  1  0            999 V2000
    6.0770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

160168  0  0  0  0  0  0  0  0999 V2000
   15.7304    0.8083    2.0342 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.7079   -1.1359    0.4059 O   0  0  0  0  0  0  0  0  0  0  0  0
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   16.8135    0.5834    2.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282221232D          

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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  6  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 15 12  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 15 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 16 25  1  6  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 28 27  1  6  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 33 34  1  1  0  0  0
 32 35  1  6  0  0  0
 31 36  1  1  0  0  0
 30 37  1  6  0  0  0
 37 38  1  0  0  0  0
 39 38  1  1  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 39 44  1  0  0  0  0
 43 45  1  1  0  0  0
 45 46  1  0  0  0  0
 42 47  1  6  0  0  0
 48 47  1  1  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 48 53  1  0  0  0  0
 52 54  1  6  0  0  0
 51 55  1  1  0  0  0
 50 56  1  6  0  0  0
 49 57  1  6  0  0  0
 41 58  1  1  0  0  0
 40 59  1  6  0  0  0
 11 60  1  1  0  0  0
  8 61  1  6  0  0  0
  5 62  1  6  0  0  0
  3 63  1  0  0  0  0
  3 64  1  0  0  0  0
  2 65  1  6  0  0  0
 66 65  1  6  0  0  0
 66 67  1  0  0  0  0
 67 68  1  0  0  0  0
 68 69  1  0  0  0  0
 69 70  1  0  0  0  0
 70 71  1  0  0  0  0
 66 71  1  0  0  0  0
 71 72  1  1  0  0  0
 70 73  1  6  0  0  0
 69 74  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0074224

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](OC[C@H]3O[C@@H](OC(=O)[C@]45CCC(C)(C)C[C@H]4C4=CC[C@@H]6[C@@]7(C)CC[C@H](O[C@@H]8OC[C@H](O)[C@H](O)[C@H]8O)C(C)(C)[C@@H]7CC[C@@]6(C)[C@]4(C)CC5)[C@H](O)[C@@H](O)[C@@H]3O)O[C@@H]2CO)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C53H86O21/c1-23-32(56)35(59)39(63)45(69-23)73-42-27(20-54)70-43(41(65)37(42)61)68-22-28-34(58)36(60)40(64)46(71-28)74-47(66)53-17-15-48(2,3)19-25(53)24-9-10-30-50(6)13-12-31(72-44-38(62)33(57)26(55)21-67-44)49(4,5)29(50)11-14-52(30,8)51(24,7)16-18-53/h9,23,25-46,54-65H,10-22H2,1-8H3/t23-,25-,26-,27+,28+,29-,30+,31-,32-,33-,34+,35+,36-,37+,38+,39+,40+,41+,42+,43+,44-,45-,46-,50-,51+,52+,53-/m0/s1

> <INCHI_KEY>
XPZZGRWYXQODIS-SEHMIGTGSA-N

> <FORMULA>
C53H86O21

> <MOLECULAR_WEIGHT>
1059.25

> <EXACT_MASS>
1058.566159789

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
160

> <JCHEM_AVERAGE_POLARIZABILITY>
112.72026812505437

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-6-({[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
0.6915033116666665

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.092625909353767

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.673329669613828

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6726844710227855

> <JCHEM_POLAR_SURFACE_AREA>
333.67

> <JCHEM_REFRACTIVITY>
255.78940000000011

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-6-({[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

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      11.344   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.114   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.344  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.804  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.034  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.742   2.920   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.510   3.643   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.334  -1.897   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.104  -3.231   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.976  -3.231   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.206  -4.565   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.976  -5.898   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.516  -5.898   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.286  -4.565   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.516  -3.231   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -3.286  -1.897   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -4.826  -4.565   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -3.286  -7.232   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -0.206  -7.232   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.976  -8.566   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -0.206  -9.899   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.334  -9.899   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       2.104 -11.233   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.334 -12.567   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -0.206 -12.567   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -0.976 -11.233   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -0.976 -13.900   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -2.516 -13.900   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       2.104 -13.900   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       1.334 -15.234   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       2.104 -16.568   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       1.334 -17.902   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      -0.206 -17.902   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -0.976 -16.568   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -0.206 -15.234   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      -2.516 -16.568   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -0.976 -19.235   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       2.104 -19.235   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0       3.644 -16.568   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0       3.644 -11.233   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       2.104  -8.566   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       5.954  -1.897   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       6.885  -2.095   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       8.264   2.104   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      12.650  -1.380   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      11.397  -2.103   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      13.654   0.770   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      14.424   2.104   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      13.654   3.437   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      14.424   4.771   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      15.964   4.771   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      16.734   3.437   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      15.964   2.104   0.000  0.00  0.00           C+0
HETATM   72  O   UNK     0      16.734   0.770   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0      18.274   3.437   0.000  0.00  0.00           O+0
HETATM   74  O   UNK     0      16.734   6.105   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   65                                                  
CONECT    3    2    4   63   64                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   62                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11   61                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   18   60                                             
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   22                                                  
CONECT   16   15   17   19   25                                             
CONECT   17   16   18                                                       
CONECT   18   17   11                                                       
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21   15                                                       
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25   16   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   37                                                  
CONECT   31   30   32   36                                                  
CONECT   32   31   33   35                                                  
CONECT   33   32   28   34                                                  
CONECT   34   33                                                            
CONECT   35   32                                                            
CONECT   36   31                                                            
CONECT   37   30   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   44                                                  
CONECT   40   39   41   59                                                  
CONECT   41   40   42   58                                                  
CONECT   42   41   43   47                                                  
CONECT   43   42   44   45                                                  
CONECT   44   43   39                                                       
CONECT   45   43   46                                                       
CONECT   46   45                                                            
CONECT   47   42   48                                                       
CONECT   48   47   49   53                                                  
CONECT   49   48   50   57                                                  
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   49                                                            
CONECT   58   41                                                            
CONECT   59   40                                                            
CONECT   60   11                                                            
CONECT   61    8                                                            
CONECT   62    5                                                            
CONECT   63    3                                                            
CONECT   64    3                                                            
CONECT   65    2   66                                                       
CONECT   66   65   67   71                                                  
CONECT   67   66   68                                                       
CONECT   68   67   69                                                       
CONECT   69   68   70   74                                                  
CONECT   70   69   71   73                                                  
CONECT   71   70   66   72                                                  
CONECT   72   71                                                            
CONECT   73   70                                                            
CONECT   74   69                                                            
MASTER        0    0    0    0    0    0    0    0   74    0  164    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₃H₈₆O₂₁

Average Mass

1059.2500 Da

Monoisotopic Mass

1058.56616 Da

IUPAC Name

(2S,3R,4S,5S,6R)-6-({[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

Traditional Name

(2S,3R,4S,5S,6R)-6-({[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-{[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy}-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylate

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](OC[C@H]3O[C@@H](OC(=O)[C@]45CCC(C)(C)C[C@H]4C4=CC[C@@H]6[C@@]7(C)CC[C@H](O[C@@H]8OC[C@H](O)[C@H](O)[C@H]8O)C(C)(C)[C@@H]7CC[C@@]6(C)[C@]4(C)CC5)[C@H](O)[C@@H](O)[C@@H]3O)O[C@@H]2CO)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C53H86O21/c1-23-32(56)35(59)39(63)45(69-23)73-42-27(20-54)70-43(41(65)37(42)61)68-22-28-34(58)36(60)40(64)46(71-28)74-47(66)53-17-15-48(2,3)19-25(53)24-9-10-30-50(6)13-12-31(72-44-38(62)33(57)26(55)21-67-44)49(4,5)29(50)11-14-52(30,8)51(24,7)16-18-53/h9,23,25-46,54-65H,10-22H2,1-8H3/t23-,25-,26-,27+,28+,29-,30+,31-,32-,33-,34+,35+,36-,37+,38+,39+,40+,41+,42+,43+,44-,45-,46-,50-,51+,52+,53-/m0/s1

InChI Key

XPZZGRWYXQODIS-SEHMIGTGSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Clematis chinensis	LOTUS Database	35616633
Cussonia arborea	LOTUS Database	35616633
Eleutherococcus senticosus	Plant	KNApSAcK
Eleutherococcus senticosus Rupr.and Maxim.	Plant	KNApSAcK
Meryta denhamii	LOTUS Database	35616633
Meryta lanceolata	LOTUS Database	35616633
Pulsatilla dahurica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Oligosaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Secondary alcohol
Carboxylic acid ester
Oxacycle
Polyol
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.63	ALOGPS
logP	0.69	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	11.67	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	333.67 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	255.79 m³·mol⁻¹	ChemAxon
Polarizability	112.72 Å³	ChemAxon
Number of Rings	9	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

C00035263

Chemspider ID

10252133

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21626481

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu Y, Wang Z, Wang C, Si H, Yu H, Li L, Fu S, Tan L, Li P, Liu J, Zhao Y: Comprehensive phytochemical analysis and sedative-hypnotic activity of two Acanthopanax species leaves. Food Funct. 2021 Mar 15;12(5):2292-2311. doi: 10.1039/d0fo02814b. [PubMed:33605281 ]
Yamauchi Y, Ge YW, Yoshimatsu K, Komastu K, Kuboyama T, Yang X, Tohda C: Memory Enhancement by Oral Administration of Extract of Eleutherococcus senticosus Leaves and Active Compounds Transferred in the Brain. Nutrients. 2019 May 22;11(5). pii: nu11051142. doi: 10.3390/nu11051142. [PubMed:31121888 ]
Kang DH, Kang OH, Li Z, Mun SH, Seo YS, Kong R, Tian Z, Liu X, Kwon DY: Anti‑inflammatory effects of Ciwujianoside C3, extracted from the leaves of Acanthopanax henryi (Oliv.) Harms, on LPS‑stimulated RAW 264.7 cells. Mol Med Rep. 2016 Oct;14(4):3749-58. doi: 10.3892/mmr.2016.5710. Epub 2016 Sep 5. [PubMed:27600484 ]

Showing NP-Card for (-)-Ciwujianoside C3 (NP0074224)

MOL for NP0074224 ((-)-Ciwujianoside C3)

3D MOL for NP0074224 ((-)-Ciwujianoside C3)

3D SDF for NP0074224 ((-)-Ciwujianoside C3)

3D-SDF for NP0074224 ((-)-Ciwujianoside C3)

PDB for NP0074224 ((-)-Ciwujianoside C3)

3D PDB for NP0074224 ((-)-Ciwujianoside C3)

SMILES for NP0074224 ((-)-Ciwujianoside C3)

INCHI for NP0074224 ((-)-Ciwujianoside C3)

Structure for NP0074224 ((-)-Ciwujianoside C3)

3D Structure for NP0074224 ((-)-Ciwujianoside C3)