NP-MRD: Showing NP-Card for (2s)-2-{[(2r)-3,5-dihydroxy-2-{[(1s,4s,5r,8r,9r,13s,14r,17s,18r)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0304760)

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Record Information

Version

2.0

Created at

2022-09-10 20:05:04 UTC

Updated at

2022-09-10 20:05:05 UTC

NP-MRD ID

NP0304760

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-{[(2r)-3,5-dihydroxy-2-{[(1s,4s,5r,8r,9r,13s,14r,17s,18r)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

(2S)-2-{[(2R)-3,5-dihydroxy-2-{[(1S,4S,5R,8R,9R,13S,14R,17S,18R)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol 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. (2s)-2-{[(2r)-3,5-dihydroxy-2-{[(1s,4s,5r,8r,9r,13s,14r,17s,18r)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Buddleja japonica, Bupleurum chinense, Bupleurum falcatum, Bupleurum fruticescens, Bupleurum kaoi, Bupleurum kunmingense, Bupleurum polyclonum, Bupleurum rockii, Clinopodium chinense, Clinopodium gracile, Clinopodium micranthum, Scrophularia kakudensis and Verbascum sinaiticum. Based on a literature review very few articles have been published on (2S)-2-{[(2R)-3,5-dihydroxy-2-{[(1S,4S,5R,8R,9R,13S,14R,17S,18R)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102222052D          

 55 62  0  0  1  0            999 V2000
    5.5779   -3.1169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0082   -2.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6139   -1.6884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0442   -0.9845    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6499   -0.2599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8251   -0.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3948   -0.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5700   -0.9221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1757   -0.1975    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7453   -0.9014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6060    0.5063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2117    1.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3869    1.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9566    0.5479    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5684    1.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3509   -0.1767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.0664    1.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4308    0.4856    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1412    0.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4803    1.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2994   -0.3015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0521   -3.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0161   -4.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1913   -4.5869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2712   -3.9247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8330   -2.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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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  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 22 21  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 29 28  1  1  0  0  0
 22 29  1  0  0  0  0
 19 29  1  0  0  0  0
 22 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 19 33  1  0  0  0  0
 14 33  1  0  0  0  0
 33 34  1  6  0  0  0
 11 35  1  0  0  0  0
  6 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  6  0  0  0
 37 38  1  0  0  0  0
  4 39  1  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 43 42  1  1  0  0  0
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 52 53  1  0  0  0  0
 41 54  1  0  0  0  0
  2 54  1  0  0  0  0
 54 55  1  0  0  0  0
M  END

     RDKit          3D

123130  0  0  0  0  0  0  0  0999 V2000
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   -0.8678    2.3256   -1.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6060   -0.1935   -1.6030 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2950   -0.3935   -2.9110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7358   -0.7409   -2.6229 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7470    1.4313   -2.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.4382    0.8869   -0.5498 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.7054    0.6233    1.0095 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.1734    0.3221    1.0292 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.7750   -0.9896    1.5323 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0212   -2.0742    1.1080 O   0  0  0  0  0  0  0  0  0  0  0  0
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 55123  1  0
M  END


  Mrv1652309102222052D          

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M  END
> <DATABASE_ID>
NP0304760

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1O[C@@H](OC2CC[C@@]3(C)[C@@H](CC[C@]4(C)[C@@H]3C=C[C@]35OC[C@@]6(CCC(C)(C)C[C@@H]36)C(O)C[C@@]45C)[C@]2(C)CO)C(O)C(O[C@@H]2OC(CO)C(O)C(O)C2O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C42H68O13/c1-21-28(46)33(55-34-31(49)30(48)29(47)22(18-43)53-34)32(50)35(52-21)54-27-10-11-37(4)23(38(27,5)19-44)8-12-39(6)24(37)9-13-42-25-16-36(2,3)14-15-41(25,20-51-42)26(45)17-40(39,42)7/h9,13,21-35,43-50H,8,10-12,14-20H2,1-7H3/t21?,22?,23-,24-,25-,26?,27?,28?,29?,30?,31?,32?,33?,34+,35+,37+,38+,39-,40+,41-,42+/m1/s1

> <INCHI_KEY>
KYWSCMDFVARMPN-RPLIYQGKSA-N

> <FORMULA>
C42H68O13

> <MOLECULAR_WEIGHT>
780.993

> <EXACT_MASS>
780.46599225

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
123

> <JCHEM_AVERAGE_POLARIZABILITY>
85.8378038848871

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-{[(2R)-3,5-dihydroxy-2-{[(1S,4S,5R,8R,9R,13S,14R,17S,18R)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
1.3959489513333319

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.468687006439165

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.9458230226885

> <JCHEM_PKA_STRONGEST_BASIC>
-2.785730265168116

> <JCHEM_POLAR_SURFACE_AREA>
207.98999999999998

> <JCHEM_REFRACTIVITY>
198.30870000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-{[(2R)-3,5-dihydroxy-2-{[(1S,4S,5R,8R,9R,13S,14R,17S,18R)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      10.412  -5.818   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.215  -4.504   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.479  -3.152   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      11.283  -1.838   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.546  -0.485   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.007  -0.446   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.204  -1.760   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.664  -1.721   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.928  -0.369   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.125  -1.683   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.731   0.945   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.995   2.298   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.456   2.337   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.652   1.023   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.928   2.382   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.388  -0.330   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.599  -1.673   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.057  -1.655   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.217  -0.323   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.130  -1.313   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.488  -0.424   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.066   1.132   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.371   0.314   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.315  -1.225   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.955  -1.946   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.077  -3.090   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.901  -3.161   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.350  -1.129   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.295   0.410   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.275   2.539   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.057   3.866   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.331   2.549   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.082   1.089   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.991   2.626   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.271   0.906   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.597   1.689   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.363   2.444   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       9.741   3.132   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      12.822  -1.877   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      13.625  -0.563   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      13.558  -3.229   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      15.098  -3.268   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      15.834  -4.621   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      15.031  -5.935   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      15.767  -7.287   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      14.963  -8.601   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0      13.424  -8.562   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      17.306  -7.326   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0      18.042  -8.679   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      18.110  -6.012   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      19.649  -6.051   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      17.373  -4.660   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      18.177  -3.346   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      12.755  -4.543   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      13.491  -5.896   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   54                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   39                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   35                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   16                                             
CONECT   10    9                                                            
CONECT   11    9   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   33                                             
CONECT   15   14                                                            
CONECT   16   14    9   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   29   33                                             
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   29   30                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29                                                       
CONECT   29   28   22   19                                                  
CONECT   30   22   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   19   14   34                                             
CONECT   34   33                                                            
CONECT   35   11    6   36   37                                             
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37                                                            
CONECT   39    4   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   54                                                  
CONECT   42   41   43                                                       
CONECT   43   42   44   52                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   48                                                  
CONECT   46   45   47                                                       
CONECT   47   46                                                            
CONECT   48   45   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51   52                                                  
CONECT   51   50                                                            
CONECT   52   50   43   53                                                  
CONECT   53   52                                                            
CONECT   54   41    2   55                                                  
CONECT   55   54                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  124    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₆₈O₁₃

Average Mass

780.9930 Da

Monoisotopic Mass

780.46599 Da

IUPAC Name

(2S)-2-{[(2R)-3,5-dihydroxy-2-{[(1S,4S,5R,8R,9R,13S,14R,17S,18R)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1O[C@@H](OC2CC[C@@]3(C)[C@@H](CC[C@]4(C)[C@@H]3C=C[C@]35OC[C@@]6(CCC(C)(C)C[C@@H]36)C(O)C[C@@]45C)[C@]2(C)CO)C(O)C(O[C@@H]2OC(CO)C(O)C(O)C2O)C1O

InChI Identifier

InChI=1S/C42H68O13/c1-21-28(46)33(55-34-31(49)30(48)29(47)22(18-43)53-34)32(50)35(52-21)54-27-10-11-37(4)23(38(27,5)19-44)8-12-39(6)24(37)9-13-42-25-16-36(2,3)14-15-41(25,20-51-42)26(45)17-40(39,42)7/h9,13,21-35,43-50H,8,10-12,14-20H2,1-7H3/t21?,22?,23-,24-,25-,26?,27?,28?,29?,30?,31?,32?,33?,34+,35+,37+,38+,39-,40+,41-,42+/m1/s1

InChI Key

KYWSCMDFVARMPN-RPLIYQGKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Buddleja japonica	LOTUS Database	35616633
Bupleurum chinense	LOTUS Database	35616633
Bupleurum falcatum	LOTUS Database	35616633
Bupleurum fruticescens	LOTUS Database	35616633
Bupleurum kaoi	LOTUS Database	35616633
Bupleurum kunmingense	LOTUS Database	35616633
Bupleurum polyclonum	LOTUS Database	35616633
Bupleurum rockii	LOTUS Database	35616633
Clinopodium chinense	LOTUS Database	35616633
Clinopodium gracile	LOTUS Database	35616633
Clinopodium micranthum	LOTUS Database	35616633
Scrophularia kakudensis	LOTUS Database	35616633
Verbascum sinaiticum	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
Steroid
O-glycosyl compound
Glycosyl compound
Disaccharide
Oxepane
Oxane
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	1.4	ChemAxon
pKa (Strongest Acidic)	11.95	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	207.99 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	198.31 m³·mol⁻¹	ChemAxon
Polarizability	85.84 Å³	ChemAxon
Number of Rings	8	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

138114182

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-{[(2r)-3,5-dihydroxy-2-{[(1s,4s,5r,8r,9r,13s,14r,17s,18r)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0304760)

MOL for NP0304760 ((2s)-2-{[(2r)-3,5-dihydroxy-2-{[(1s,4s,5r,8r,9r,13s,14r,17s,18r)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0304760 ((2s)-2-{[(2r)-3,5-dihydroxy-2-{[(1s,4s,5r,8r,9r,13s,14r,17s,18r)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0304760 ((2s)-2-{[(2r)-3,5-dihydroxy-2-{[(1s,4s,5r,8r,9r,13s,14r,17s,18r)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0304760 ((2s)-2-{[(2r)-3,5-dihydroxy-2-{[(1s,4s,5r,8r,9r,13s,14r,17s,18r)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0304760 ((2s)-2-{[(2r)-3,5-dihydroxy-2-{[(1s,4s,5r,8r,9r,13s,14r,17s,18r)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0304760 ((2s)-2-{[(2r)-3,5-dihydroxy-2-{[(1s,4s,5r,8r,9r,13s,14r,17s,18r)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0304760 ((2s)-2-{[(2r)-3,5-dihydroxy-2-{[(1s,4s,5r,8r,9r,13s,14r,17s,18r)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0304760 ((2s)-2-{[(2r)-3,5-dihydroxy-2-{[(1s,4s,5r,8r,9r,13s,14r,17s,18r)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0304760 ((2s)-2-{[(2r)-3,5-dihydroxy-2-{[(1s,4s,5r,8r,9r,13s,14r,17s,18r)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0304760 ((2s)-2-{[(2r)-3,5-dihydroxy-2-{[(1s,4s,5r,8r,9r,13s,14r,17s,18r)-2-hydroxy-9-(hydroxymethyl)-4,5,9,13,20,20-hexamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-10-yl]oxy}-6-methyloxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)