NP-MRD: Showing NP-Card for 4-(acetyloxy)-5-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate (NP0214114)

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Record Information

Version

2.0

Created at

2022-09-05 13:19:09 UTC

Updated at

2022-09-05 13:19:09 UTC

NP-MRD ID

NP0214114

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(acetyloxy)-5-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate

Description

4-(Acetyloxy)-5-hydroxy-2-({13-hydroxy-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,2,6,6,11,15-hexamethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl}oxy)oxan-3-yl acetate belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus. 4-(acetyloxy)-5-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate is found in Astragalus sieversianus. 4-(Acetyloxy)-5-hydroxy-2-({13-hydroxy-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,2,6,6,11,15-hexamethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-5-yl}oxy)oxan-3-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161522512D          

 62 68  0  0  0  0            999 V2000
   11.2951   -0.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4829   -0.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2026   -1.6747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9511   -0.2681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1390   -0.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8587   -1.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3905   -1.8199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0466   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7951    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2632    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4511    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1708   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3587   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5466   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1072    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7633    1.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4830    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.0743   -0.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7345   -0.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9224   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3905   -0.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0307   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5607    0.9312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0195    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8685    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6892   -2.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2608   -2.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2840   -1.4456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8557    2.4498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3239    3.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5117    2.9353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799    3.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678    3.4208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6360    4.0515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2602    4.3420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7284    4.9727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0723    4.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3526    5.2631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6041    3.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4163    4.0017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.8025    2.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5311    1.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6072    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5435    1.4789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6360    2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 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
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
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 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
 27 33  1  0  0  0  0
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  5 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  2  0  0  0  0
 60 62  1  0  0  0  0
M  END

     RDKit          3D

138144  0  0  0  0  0  0  0  0999 V2000
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   -7.7936    1.8067    2.2561 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004161522512D          

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M  END
> <DATABASE_ID>
NP0214114

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C(O)COC(OC2CCC3(C)C(C(CC4C5(C)CC(O)C(C6(C)CCC(O6)C(C)(C)O)C5(C)CCC34C)OC3OC(CO)C(O)C(O)C3O)C2(C)C)C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C46H76O16/c1-22(48)57-34-25(51)21-56-39(35(34)58-23(2)49)61-29-12-14-43(8)37(40(29,3)4)26(59-38-33(54)32(53)31(52)27(20-47)60-38)18-28-42(43,7)16-17-44(9)36(24(50)19-45(28,44)10)46(11)15-13-30(62-46)41(5,6)55/h24-39,47,50-55H,12-21H2,1-11H3

> <INCHI_KEY>
LPDRYJZGRMHSIY-UHFFFAOYSA-N

> <FORMULA>
C46H76O16

> <MOLECULAR_WEIGHT>
885.098

> <EXACT_MASS>
884.513336367

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
138

> <JCHEM_AVERAGE_POLARIZABILITY>
95.27859560040403

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-(acetyloxy)-5-hydroxy-2-({13-hydroxy-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,2,6,6,11,15-hexamethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxy)oxan-3-yl acetate

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
1.4790023579999998

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.95925962924105

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.17258583234889

> <JCHEM_PKA_STRONGEST_BASIC>
-2.875943152661687

> <JCHEM_POLAR_SURFACE_AREA>
240.35999999999996

> <JCHEM_REFRACTIVITY>
219.28630000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(acetyloxy)-5-hydroxy-2-({13-hydroxy-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,2,6,6,11,15-hexamethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxy)oxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      21.084  -1.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.568  -1.678   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      19.045  -3.126   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      18.575  -0.500   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      17.059  -0.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.536  -2.220   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      17.529  -3.397   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      15.020  -2.491   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      14.028  -1.314   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.551   0.135   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.605  -1.308   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.047   1.738   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.355   2.629   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.286  -2.293   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.868  -0.413   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.490  -1.139   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.219  -2.655   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.306  -2.866   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -1.286  -3.766   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -2.354  -4.876   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -0.176  -4.833   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -2.397  -2.698   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       9.064   4.573   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       8.071   5.750   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       6.555   5.479   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       5.563   6.657   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       4.047   6.386   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       3.054   7.563   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0       6.086   8.105   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0       5.093   9.282   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       7.602   8.376   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       8.125   9.824   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       8.594   7.199   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      10.110   7.470   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      10.831   3.743   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      12.191   3.252   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      16.067   0.406   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      16.590   1.854   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      15.597   3.032   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      14.081   2.761   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      16.120   4.480   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   58                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   58                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   55                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17   21                                             
CONECT   16   15                                                            
CONECT   17   15   18   55                                                  
CONECT   18   17   19   43                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   31                                                  
CONECT   21   20   15   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   31                                             
CONECT   26   25                                                            
CONECT   27   25   28   33                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   20   25   32                                             
CONECT   32   31                                                            
CONECT   33   27   34   35   38                                             
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37   33                                                       
CONECT   39   37   40   41   42                                             
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   39                                                            
CONECT   43   18   44                                                       
CONECT   44   43   45   53                                                  
CONECT   45   44   46                                                       
CONECT   46   45   47   49                                                  
CONECT   47   46   48                                                       
CONECT   48   47                                                            
CONECT   49   46   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   44   54                                                  
CONECT   54   53                                                            
CONECT   55   17   12   56   57                                             
CONECT   56   55                                                            
CONECT   57   55                                                            
CONECT   58   10    5   59                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61   62                                                  
CONECT   61   60                                                            
CONECT   62   60                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  136    0
END

View in JSmol

Synonyms

Value	Source
4-(Acetyloxy)-5-hydroxy-2-({13-hydroxy-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,2,6,6,11,15-hexamethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0,.0,]heptadecan-5-yl}oxy)oxan-3-yl acetic acid	Generator
4-(Acetyloxy)-5-hydroxy-2-({13-hydroxy-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,2,6,6,11,15-hexamethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxy)oxan-3-yl acetic acid	Generator

Chemical Formula

C₄₆H₇₆O₁₆

Average Mass

885.0980 Da

Monoisotopic Mass

884.51334 Da

IUPAC Name

4-(acetyloxy)-5-hydroxy-2-({13-hydroxy-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-1,2,6,6,11,15-hexamethyl-8-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl}oxy)oxan-3-yl acetate

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C(O)COC(OC2CCC3(C)C(C(CC4C5(C)CC(O)C(C6(C)CCC(O6)C(C)(C)O)C5(C)CCC34C)OC3OC(CO)C(O)C(O)C3O)C2(C)C)C1OC(C)=O

InChI Identifier

InChI=1S/C46H76O16/c1-22(48)57-34-25(51)21-56-39(35(34)58-23(2)49)61-29-12-14-43(8)37(40(29,3)4)26(59-38-33(54)32(53)31(52)27(20-47)60-38)18-28-42(43,7)16-17-44(9)36(24(50)19-45(28,44)10)46(11)15-13-30(62-46)41(5,6)55/h24-39,47,50-55H,12-21H2,1-11H3

InChI Key

LPDRYJZGRMHSIY-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
Astragalus sieversianus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacin glycosides. These are polycyclic compounds containing a carbohydrate derivative glycosidically linked to a curcubitane nucleus.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Cucurbitacin glycosides

Alternative Parents

Substituents

Cucurbitacin glycoside skeleton
Triterpene saponin
Triterpene glycoside
Triterpenoid
Hydroxysteroid
16-hydroxysteroid
Glycosyl compound
O-glycosyl compound
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Cyclic alcohol
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Acetal
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organic oxide
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen 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	2.78	ALOGPS
logP	1.48	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	12.17	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	240.36 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	219.29 m³·mol⁻¹	ChemAxon
Polarizability	95.28 Å³	ChemAxon
Number of Rings	7	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 4-(acetyloxy)-5-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate (NP0214114)

MOL for NP0214114 (4-(acetyloxy)-5-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

3D MOL for NP0214114 (4-(acetyloxy)-5-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

3D SDF for NP0214114 (4-(acetyloxy)-5-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

3D-SDF for NP0214114 (4-(acetyloxy)-5-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

PDB for NP0214114 (4-(acetyloxy)-5-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

3D PDB for NP0214114 (4-(acetyloxy)-5-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

SMILES for NP0214114 (4-(acetyloxy)-5-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

INCHI for NP0214114 (4-(acetyloxy)-5-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

Structure for NP0214114 (4-(acetyloxy)-5-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)

3D Structure for NP0214114 (4-(acetyloxy)-5-hydroxy-2-({2-hydroxy-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,6,6,9a,9b,11a-hexamethyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-dodecahydrocyclopenta[a]phenanthren-7-yl}oxy)oxan-3-yl acetate)