Np mrd loader

Showing NP-Card for (+)-Sandrosaponin III (NP0075759)

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Record Information
Version2.0
Created at2022-04-28 20:59:53 UTC
Updated at2022-04-28 20:59:54 UTC
NP-MRD IDNP0075759
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Sandrosaponin III
Description(1S,2S,4S,5R,8R,9R,10S,13S,14R,17R,18R,20R)-10-{[(2R,3R,4S,5S,6R)-4-{[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]oxy}-5-hydroxy-6-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20-pentamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracos-15-ene-20-carboxylic acid 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. (+)-Sandrosaponin III is found in Bupleurum rigidum L. Based on a literature review very few articles have been published on (1S,2S,4S,5R,8R,9R,10S,13S,14R,17R,18R,20R)-10-{[(2R,3R,4S,5S,6R)-4-{[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]oxy}-5-hydroxy-6-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20-pentamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracos-15-ene-20-carboxylic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0075759 ((+)-Sandrosaponin III)


  Mrv1652304282222592D          

 72 80  0  0  1  0            999 V2000
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M  END
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3D MOL for NP0075759 ((+)-Sandrosaponin III)

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3D SDF for NP0075759 ((+)-Sandrosaponin III)

  Mrv1652304282222592D          

 72 80  0  0  1  0            999 V2000
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  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  1  0  0  0
  8 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
  7 14  1  1  0  0  0
 12 15  1  0  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
 17 19  1  1  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  1  0  0  0
 22 24  1  1  0  0  0
 22 25  1  6  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 16 28  1  1  0  0  0
 28 29  1  0  0  0  0
 12 29  1  6  0  0  0
 11 30  1  6  0  0  0
  8 31  1  1  0  0  0
  5 32  1  1  0  0  0
  3 33  1  1  0  0  0
  3 34  1  6  0  0  0
 34 35  1  0  0  0  0
  2 36  1  1  0  0  0
 37 36  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 37 42  1  0  0  0  0
 42 43  1  6  0  0  0
 44 43  1  1  0  0  0
 44 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 44 49  1  0  0  0  0
 48 50  1  1  0  0  0
 50 51  1  0  0  0  0
 47 52  1  6  0  0  0
 46 53  1  1  0  0  0
 45 54  1  6  0  0  0
 41 55  1  1  0  0  0
 56 55  1  6  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 56 61  1  0  0  0  0
 61 62  1  1  0  0  0
 60 63  1  6  0  0  0
 59 64  1  1  0  0  0
 64 65  1  0  0  0  0
 65 66  2  0  0  0  0
 65 67  2  0  0  0  0
 65 68  1  0  0  0  0
 58 69  1  6  0  0  0
 69 70  1  0  0  0  0
 40 71  1  1  0  0  0
 39 72  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0075759

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1O[C@@H](O[C@H]2CC[C@@]3(C)[C@@H](CC[C@]4(C)[C@@H]3C=C[C@@]35OC[C@@]6(CC[C@](C)(C[C@@H]36)C(O)=O)[C@@H](O)C[C@@]45C)[C@]2(C)CO)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](OS(O)(=O)=O)[C@H](O)[C@H]2O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C48H76O23S/c1-21-29(53)36(69-39-34(58)32(56)35(23(18-50)67-39)71-72(61,62)63)37(70-38-33(57)31(55)30(54)22(17-49)66-38)40(65-21)68-28-9-10-43(3)24(44(28,4)19-51)7-11-45(5)25(43)8-12-48-26-15-42(2,41(59)60)13-14-47(26,20-64-48)27(52)16-46(45,48)6/h8,12,21-40,49-58H,7,9-11,13-20H2,1-6H3,(H,59,60)(H,61,62,63)/t21-,22-,23-,24-,25-,26-,27+,28+,29+,30-,31+,32-,33-,34-,35-,36+,37-,38+,39+,40+,42-,43+,44+,45-,46+,47-,48-/m1/s1

> <INCHI_KEY>
UTCQBPCYERIKAV-INUXRHAGSA-N

> <FORMULA>
C48H76O23S

> <MOLECULAR_WEIGHT>
1053.17

> <EXACT_MASS>
1052.449809881

> <JCHEM_ACCEPTOR_COUNT>
22

> <JCHEM_ATOM_COUNT>
148

> <JCHEM_AVERAGE_POLARIZABILITY>
44.742150837447426

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4S,5R,8R,9R,10S,13S,14R,17R,18R,20R)-10-{[(2R,3R,4S,5S,6R)-4-{[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]oxy}-5-hydroxy-6-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20-pentamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracos-15-ene-20-carboxylic acid

> <ALOGPS_LOGP>
0.32

> <JCHEM_LOGP>
-2.9910164026542274

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.343141275703718

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.0157262322492704

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6193476885322626

> <JCHEM_POLAR_SURFACE_AREA>
367.81

> <JCHEM_REFRACTIVITY>
242.43100000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,5R,8R,9R,10S,13S,14R,17R,18R,20R)-10-{[(2R,3R,4S,5S,6R)-4-{[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]oxy}-5-hydroxy-6-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20-pentamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracos-15-ene-20-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0075759 ((+)-Sandrosaponin III)
Download
PDB for NP0075759 ((+)-Sandrosaponin III)
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       8.561   0.992   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.348   2.315   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.595   3.659   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.055   3.679   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.268   2.355   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.021   1.012   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.728   2.375   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.976   3.719   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.763   5.042   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.303   5.022   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.398   3.777   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.551   2.354   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.407   1.032   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.950   1.034   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.480   3.148   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.890   3.853   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.024   5.198   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.630   5.228   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.710   6.552   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.184   3.019   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.110   1.481   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.740   0.776   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.733   1.735   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.048  -0.547   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.396  -0.617   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.931  -0.745   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.518  -1.882   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.153   2.221   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.216   1.348   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.217   5.081   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.175   5.246   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.481   1.032   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.912   4.458   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.669   5.197   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.038   5.902   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      10.888   2.295   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      11.640   0.952   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      10.853  -0.372   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      11.606  -1.715   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      13.146  -1.735   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      13.933  -0.412   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      13.180   0.932   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      13.967   2.255   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      15.507   2.235   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      16.294   3.559   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      17.834   3.539   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      18.587   2.196   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      17.800   0.872   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      16.260   0.892   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      18.552  -0.472   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      20.092  -0.492   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      20.127   2.176   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      18.622   4.863   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      15.542   4.903   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      15.473  -0.432   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      16.225  -1.775   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      17.765  -1.795   0.000  0.00  0.00           O+0
HETATM   58  C   UNK     0      18.518  -3.139   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      17.731  -4.462   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      16.191  -4.442   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      15.438  -3.099   0.000  0.00  0.00           C+0
HETATM   62  O   UNK     0      13.898  -3.079   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      15.403  -5.766   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      18.483  -5.806   0.000  0.00  0.00           O+0
HETATM   65  S   UNK     0      20.023  -5.826   0.000  0.00  0.00           S+0
HETATM   66  O   UNK     0      20.003  -7.366   0.000  0.00  0.00           O+0
HETATM   67  O   UNK     0      20.043  -4.286   0.000  0.00  0.00           O+0
HETATM   68  O   UNK     0      21.563  -5.846   0.000  0.00  0.00           O+0
HETATM   69  C   UNK     0      20.058  -3.159   0.000  0.00  0.00           C+0
HETATM   70  O   UNK     0      20.845  -1.835   0.000  0.00  0.00           O+0
HETATM   71  O   UNK     0      12.965  -3.265   0.000  0.00  0.00           O+0
HETATM   72  C   UNK     0      10.818  -3.039   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   36                                                  
CONECT    3    2    4   33   34                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   32                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11   31                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   18   30                                             
CONECT   12   11   13   15   29                                             
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   23                                                  
CONECT   16   15   17   20   28                                             
CONECT   17   16   18   19                                                  
CONECT   18   17   11                                                       
CONECT   19   17                                                            
CONECT   20   16   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22   15                                                       
CONECT   24   22                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   16   29                                                       
CONECT   29   28   12                                                       
CONECT   30   11                                                            
CONECT   31    8                                                            
CONECT   32    5                                                            
CONECT   33    3                                                            
CONECT   34    3   35                                                       
CONECT   35   34                                                            
CONECT   36    2   37                                                       
CONECT   37   36   38   42                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40   72                                                  
CONECT   40   39   41   71                                                  
CONECT   41   40   42   55                                                  
CONECT   42   41   37   43                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   49                                                  
CONECT   45   44   46   54                                                  
CONECT   46   45   47   53                                                  
CONECT   47   46   48   52                                                  
CONECT   48   47   49   50                                                  
CONECT   49   48   44                                                       
CONECT   50   48   51                                                       
CONECT   51   50                                                            
CONECT   52   47                                                            
CONECT   53   46                                                            
CONECT   54   45                                                            
CONECT   55   41   56                                                       
CONECT   56   55   57   61                                                  
CONECT   57   56   58                                                       
CONECT   58   57   59   69                                                  
CONECT   59   58   60   64                                                  
CONECT   60   59   61   63                                                  
CONECT   61   60   56   62                                                  
CONECT   62   61                                                            
CONECT   63   60                                                            
CONECT   64   59   65                                                       
CONECT   65   64   66   67   68                                             
CONECT   66   65                                                            
CONECT   67   65                                                            
CONECT   68   65                                                            
CONECT   69   58   70                                                       
CONECT   70   69                                                            
CONECT   71   40                                                            
CONECT   72   39                                                            
MASTER        0    0    0    0    0    0    0    0   72    0  160    0
END

Download
3D PDB for NP0075759 ((+)-Sandrosaponin III)
Download
SMILES for NP0075759 ((+)-Sandrosaponin III)
C[C@H]1O[C@@H](O[C@H]2CC[C@@]3(C)[C@@H](CC[C@]4(C)[C@@H]3C=C[C@@]35OC[C@@]6(CC[C@](C)(C[C@@H]36)C(O)=O)[C@@H](O)C[C@@]45C)[C@]2(C)CO)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](OS(O)(=O)=O)[C@H](O)[C@H]2O)[C@H]1O
Download
INCHI for NP0075759 ((+)-Sandrosaponin III)
InChI=1S/C48H76O23S/c1-21-29(53)36(69-39-34(58)32(56)35(23(18-50)67-39)71-72(61,62)63)37(70-38-33(57)31(55)30(54)22(17-49)66-38)40(65-21)68-28-9-10-43(3)24(44(28,4)19-51)7-11-45(5)25(43)8-12-48-26-15-42(2,41(59)60)13-14-47(26,20-64-48)27(52)16-46(45,48)6/h8,12,21-40,49-58H,7,9-11,13-20H2,1-6H3,(H,59,60)(H,61,62,63)/t21-,22-,23-,24-,25-,26-,27+,28+,29+,30-,31+,32-,33-,34-,35-,36+,37-,38+,39+,40+,42-,43+,44+,45-,46+,47-,48-/m1/s1
Download
View in JSmol
Synonyms
ValueSource
(1S,2S,4S,5R,8R,9R,10S,13S,14R,17R,18R,20R)-10-{[(2R,3R,4S,5S,6R)-4-{[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]oxy}-5-hydroxy-6-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20-pentamethyl-24-oxahexacyclo[15.5.2.0,.0,.0,.0,]tetracos-15-ene-20-carboxylateGenerator
(1S,2S,4S,5R,8R,9R,10S,13S,14R,17R,18R,20R)-10-{[(2R,3R,4S,5S,6R)-4-{[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(sulphooxy)oxan-2-yl]oxy}-5-hydroxy-6-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20-pentamethyl-24-oxahexacyclo[15.5.2.0,.0,.0,.0,]tetracos-15-ene-20-carboxylateGenerator
(1S,2S,4S,5R,8R,9R,10S,13S,14R,17R,18R,20R)-10-{[(2R,3R,4S,5S,6R)-4-{[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(sulphooxy)oxan-2-yl]oxy}-5-hydroxy-6-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20-pentamethyl-24-oxahexacyclo[15.5.2.0,.0,.0,.0,]tetracos-15-ene-20-carboxylic acidGenerator
Chemical FormulaC48H76O23S
Average Mass1053.1700 Da
Monoisotopic Mass1052.44981 Da
IUPAC Name(1S,2S,4S,5R,8R,9R,10S,13S,14R,17R,18R,20R)-10-{[(2R,3R,4S,5S,6R)-4-{[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]oxy}-5-hydroxy-6-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20-pentamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracos-15-ene-20-carboxylic acid
Traditional Name(1S,2S,4S,5R,8R,9R,10S,13S,14R,17R,18R,20R)-10-{[(2R,3R,4S,5S,6R)-4-{[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-(sulfooxy)oxan-2-yl]oxy}-5-hydroxy-6-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20-pentamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracos-15-ene-20-carboxylic acid
CAS Registry NumberNot Available
SMILES
C[C@H]1O[C@@H](O[C@H]2CC[C@@]3(C)[C@@H](CC[C@]4(C)[C@@H]3C=C[C@@]35OC[C@@]6(CC[C@](C)(C[C@@H]36)C(O)=O)[C@@H](O)C[C@@]45C)[C@]2(C)CO)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](OS(O)(=O)=O)[C@H](O)[C@H]2O)[C@H]1O
InChI Identifier
InChI=1S/C48H76O23S/c1-21-29(53)36(69-39-34(58)32(56)35(23(18-50)67-39)71-72(61,62)63)37(70-38-33(57)31(55)30(54)22(17-49)66-38)40(65-21)68-28-9-10-43(3)24(44(28,4)19-51)7-11-45(5)25(43)8-12-48-26-15-42(2,41(59)60)13-14-47(26,20-64-48)27(52)16-46(45,48)6/h8,12,21-40,49-58H,7,9-11,13-20H2,1-6H3,(H,59,60)(H,61,62,63)/t21-,22-,23-,24-,25-,26-,27+,28+,29+,30-,31+,32-,33-,34-,35-,36+,37-,38+,39+,40+,42-,43+,44+,45-,46+,47-,48-/m1/s1
InChI KeyUTCQBPCYERIKAV-INUXRHAGSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Bupleurum rigidumPlant
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.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTerpene glycosides  
Direct ParentTriterpene saponins  
Alternative Parents
Substituents
  • Triterpene saponin
    • 

  • Triterpenoid
    • 

  • Steroid
    • 

  • Disaccharide sulfate
    • 

  • O-glycosyl compound
    • 

  • Glycosyl compound
    • 

  • Disaccharide
    • 

  • Oxepane
    • 

  • Sulfuric acid ester
    • 

  • Alkyl sulfate
    • 

  • Sulfate-ester
    • 

  • Sulfuric acid monoester
    • 

  • Oxane
    • 

  • Tetrahydrofuran
    • 

  • Organic sulfuric acid or derivatives
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Polyol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Acetal
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP0.32ALOGPS
logP-3ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)-2ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area367.81 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity242.43 m³·mol⁻¹ChemAxon
Polarizability44.74 ųChemAxon
Number of Rings9ChemAxon
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 Compound163099380  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available