NP-MRD: Showing NP-Card for 10-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-21-one (NP0322215)

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Record Information

Version

2.0

Created at

2022-09-12 00:51:44 UTC

Updated at

2022-09-12 00:51:44 UTC

NP-MRD ID

NP0322215

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-21-one

Description

10-[(3-{[4,5-Dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracos-15-en-21-one 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. 10-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-21-one is found in Bupleurum rotundifolium. 10-[(3-{[4,5-Dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracos-15-en-21-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171504222D          

 65 73  0  0  0  0            999 V2000
   10.6703    2.4724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8456    2.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4152    1.7893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5905    1.8101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1601    1.1062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5545    0.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3792    0.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8096    1.0647    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7736   -0.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5983   -0.3846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3432   -1.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7376   -1.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3072   -2.4962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5185   -1.0469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1241   -0.3222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2994   -0.3015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8690   -1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2633   -1.7299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0881   -1.7507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8330   -2.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2273   -3.1584    0.0000 O   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
    5.5779   -3.1169    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  0  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  0  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  0  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  0  0  0  0  0  0  0  0  0  0
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    2.3509   -0.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2701    0.1681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5114   -1.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0185   -1.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0414   -1.6552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1877   -0.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1579    0.2198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1472    1.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4308    0.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.1412    0.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1961    2.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3714    2.5555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6265    3.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2321    3.9632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4512    3.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8816    3.9216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
  6 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
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  0  0  0  0
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 32 33  1  0  0  0  0
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 35 36  1  0  0  0  0
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 40 55  1  0  0  0  0
 55 56  1  0  0  0  0
 32 57  1  0  0  0  0
 27 57  1  0  0  0  0
 57 58  1  0  0  0  0
 57 59  1  0  0  0  0
  4 60  1  0  0  0  0
 60 61  1  0  0  0  0
 60 62  1  0  0  0  0
 62 63  1  0  0  0  0
 62 64  1  0  0  0  0
  2 64  1  0  0  0  0
 64 65  1  0  0  0  0
M  END

     RDKit          3D

141149  0  0  0  0  0  0  0  0999 V2000
   -5.1447   -4.0491   -1.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9400   -3.5253   -1.8232 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.1277    0.3556    0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004171504222D          

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M  END
> <DATABASE_ID>
NP0322215

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2C(O)C(O)C(CO)OC2OC2C(O)C(O)C(C)OC2OC2CCC3(C)C(CCC4(C)C3C=CC35OCC6(CC(=O)C(C)(C)CC36)C(O)CC45C)C2(C)C)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C48H76O17/c1-21-30(52)33(55)36(58)39(60-21)64-38-35(57)32(54)23(19-49)62-41(38)65-37-34(56)31(53)22(2)61-40(37)63-29-12-13-44(7)24(43(29,5)6)10-14-45(8)25(44)11-15-48-26-16-42(3,4)27(50)18-47(26,20-59-48)28(51)17-46(45,48)9/h11,15,21-26,28-41,49,51-58H,10,12-14,16-20H2,1-9H3

> <INCHI_KEY>
RYKWBOUIIFTUAC-UHFFFAOYSA-N

> <FORMULA>
C48H76O17

> <MOLECULAR_WEIGHT>
925.119

> <EXACT_MASS>
924.508250987

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
141

> <JCHEM_AVERAGE_POLARIZABILITY>
98.44074686565779

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-21-one

> <ALOGPS_LOGP>
1.81

> <JCHEM_LOGP>
1.2855110676666663

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.51980381137734

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.012489213750477

> <JCHEM_PKA_STRONGEST_BASIC>
-2.983044668475686

> <JCHEM_POLAR_SURFACE_AREA>
263.74999999999994

> <JCHEM_REFRACTIVITY>
228.09680000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-21-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      19.918   4.615   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.378   4.654   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      17.575   3.340   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      16.036   3.379   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      15.232   2.065   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      15.968   0.712   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.508   0.674   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      18.311   1.987   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      18.244  -0.679   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      19.784  -0.718   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      17.441  -1.993   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.177  -3.346   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      17.373  -4.660   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      15.901  -1.954   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      15.165  -0.602   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      13.625  -0.563   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.822  -1.877   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.558  -3.229   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      15.098  -3.268   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.755  -4.543   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.491  -5.896   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.215  -4.504   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.412  -5.818   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.479  -3.152   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      11.283  -1.838   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.546  -0.485   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.007  -0.446   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.204  -1.760   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.664  -1.721   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.928  -0.369   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.125  -1.683   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.731   0.945   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.995   2.298   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.456   2.337   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.652   1.023   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.928   2.382   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.388  -0.330   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.599  -1.673   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.057  -1.655   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       1.217  -0.323   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -0.130  -1.313   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -1.488  -0.424   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -1.066   1.132   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -2.371   0.314   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      -2.315  -1.225   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      -3.620  -2.043   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      -0.955  -1.946   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -1.901  -3.161   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       0.077  -3.090   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       0.350  -1.129   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       0.295   0.410   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      -0.275   2.539   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      -1.057   3.866   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       1.331   2.549   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       2.082   1.089   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0       1.991   2.626   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       8.271   0.906   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       8.363   2.444   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       9.597   1.689   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      15.299   4.731   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      13.760   4.770   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      16.103   6.045   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      15.367   7.398   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0      17.642   6.007   0.000  0.00  0.00           C+0
HETATM   65  O   UNK     0      18.446   7.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   64                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   60                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14    6   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   17   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   57                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32   37                                             
CONECT   31   30                                                            
CONECT   32   30   33   57                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37   55                                             
CONECT   36   35                                                            
CONECT   37   35   30   38                                                  
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41   51   55                                             
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   51   52                                             
CONECT   44   43   45                                                       
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48   49   50                                             
CONECT   48   47                                                            
CONECT   49   47                                                            
CONECT   50   47   51                                                       
CONECT   51   50   40   43                                                  
CONECT   52   43   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52   55                                                       
CONECT   55   54   35   40   56                                             
CONECT   56   55                                                            
CONECT   57   32   27   58   59                                             
CONECT   58   57                                                            
CONECT   59   57                                                            
CONECT   60    4   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60   63   64                                                  
CONECT   63   62                                                            
CONECT   64   62    2   65                                                  
CONECT   65   64                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  146    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₈H₇₆O₁₇

Average Mass

925.1190 Da

Monoisotopic Mass

924.50825 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1OC(OC2C(O)C(O)C(CO)OC2OC2C(O)C(O)C(C)OC2OC2CCC3(C)C(CCC4(C)C3C=CC35OCC6(CC(=O)C(C)(C)CC36)C(O)CC45C)C2(C)C)C(O)C(O)C1O

InChI Identifier

InChI=1S/C48H76O17/c1-21-30(52)33(55)36(58)39(60-21)64-38-35(57)32(54)23(19-49)62-41(38)65-37-34(56)31(53)22(2)61-40(37)63-29-12-13-44(7)24(43(29,5)6)10-14-45(8)25(44)11-15-48-26-16-42(3,4)27(50)18-47(26,20-59-48)28(51)17-46(45,48)9/h11,15,21-26,28-41,49,51-58H,10,12-14,16-20H2,1-9H3

InChI Key

RYKWBOUIIFTUAC-UHFFFAOYSA-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
Bupleurum rotundifolium	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
Oxepane
Oxane
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Cyclic ketone
Ketone
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Dialkyl ether
Ether
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	1.81	ALOGPS
logP	1.29	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.01	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	263.75 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	228.1 m³·mol⁻¹	ChemAxon
Polarizability	98.44 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-21-one (NP0322215)

MOL for NP0322215 (10-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-21-one)

3D MOL for NP0322215 (10-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-21-one)

3D SDF for NP0322215 (10-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-21-one)

3D-SDF for NP0322215 (10-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-21-one)

PDB for NP0322215 (10-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-21-one)

3D PDB for NP0322215 (10-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-21-one)

SMILES for NP0322215 (10-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-21-one)

INCHI for NP0322215 (10-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-21-one)

Structure for NP0322215 (10-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-21-one)

3D Structure for NP0322215 (10-[(3-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl)oxy]-2-hydroxy-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]tetracos-15-en-21-one)