NP-MRD: Showing NP-Card for [3,4,5-tris(acetyloxy)-6-{[1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2,7-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}oxan-2-yl]methyl acetate (NP0204479)

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Record Information

Version

2.0

Created at

2022-09-05 00:09:21 UTC

Updated at

2022-09-05 00:09:21 UTC

NP-MRD ID

NP0204479

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[3,4,5-tris(acetyloxy)-6-{[1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2,7-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}oxan-2-yl]methyl acetate

Description

[3,4,5-Tris(acetyloxy)-6-{[14-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-5,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-4-yl]oxy}oxan-2-yl]methyl 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. [3,4,5-tris(acetyloxy)-6-{[1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2,7-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}oxan-2-yl]methyl acetate is found in Picrorhiza kurrooa. [3,4,5-Tris(acetyloxy)-6-{[14-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-5,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-7-en-4-yl]oxy}oxan-2-yl]methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241500282D          

 59 63  0  0  0  0            999 V2000
   10.7920    2.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9799    1.9145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4481    2.5452    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6996    1.1386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8875    0.9934    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
    7.7951    0.0722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7026   -0.8489    0.0000 O   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
    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
    4.0148    0.1221    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
    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
    0.4083   -0.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7109   -1.2992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5533   -1.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640   -1.3314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8642   -2.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3578   -2.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4594   -2.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2767   -2.6340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3466   -1.9296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5723   -3.5641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6353    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6328    1.6026    0.0000 C   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
    7.2632    0.7029    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
    7.7663   -2.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9542   -2.2555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4223   -1.6248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6739   -3.0315    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
    9.1102   -2.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2981   -2.7410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6420   -3.2265    0.0000 C   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
    9.9511   -0.2681    0.0000 O   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
   11.2951   -0.7535    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
  7  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  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 16 27  1  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
 13 40  1  0  0  0  0
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 40 42  1  0  0  0  0
 40 43  1  0  0  0  0
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  8 45  1  0  0  0  0
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  6 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 57 59  1  0  0  0  0
M  END

     RDKit          3D

127131  0  0  0  0  0  0  0  0999 V2000
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   -6.7463   -1.3488   -4.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.8896    0.6255   -2.9349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6857    0.0264   -1.5605 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6839    0.7677   -0.9654 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4876    0.5948    0.3748 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7803   -0.5230    0.7523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5710   -0.2127    1.3451 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3881   -0.8345    0.5908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0813   -0.7732    1.2966 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1852   -0.1895    2.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9280    0.0682    3.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2036   -0.3081    2.5806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1530    0.3981    1.2725 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0926   -0.3077    0.4687 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5344    0.4404   -0.7023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7364   -1.5457   -0.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


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M  END
> <DATABASE_ID>
NP0204479

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1OC(OC2CC3C(=CCC4C5(C)CC(O)C(C(C)(O)C(=O)CCC(C)(C)O)C5(C)CCC34C)C(C)(C)C2O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C44H68O15/c1-22(45)54-21-30-33(55-23(2)46)34(56-24(3)47)35(57-25(4)48)38(59-30)58-29-19-27-26(40(7,8)37(29)51)13-14-31-41(27,9)17-18-42(10)36(28(49)20-43(31,42)11)44(12,53)32(50)15-16-39(5,6)52/h13,27-31,33-38,49,51-53H,14-21H2,1-12H3

> <INCHI_KEY>
UXHIMBDZUHTFOC-UHFFFAOYSA-N

> <FORMULA>
C44H68O15

> <MOLECULAR_WEIGHT>
837.013

> <EXACT_MASS>
836.45582149

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
127

> <JCHEM_AVERAGE_POLARIZABILITY>
90.18217314952574

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[3,4,5-tris(acetyloxy)-6-{[14-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-5,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-4-yl]oxy}oxan-2-yl]methyl acetate

> <ALOGPS_LOGP>
3.54

> <JCHEM_LOGP>
2.4318126043333317

> <ALOGPS_LOGS>
-5.34

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.725777281857109

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.870079418092779

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6327209707876023

> <JCHEM_POLAR_SURFACE_AREA>
221.64999999999998

> <JCHEM_REFRACTIVITY>
209.97020000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.85e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[3,4,5-tris(acetyloxy)-6-{[14-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-5,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-4-yl]oxy}oxan-2-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      20.145   3.845   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.629   3.574   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      17.636   4.751   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      18.106   2.125   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      16.590   1.854   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.067   0.406   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      14.551   0.135   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      14.028  -1.314   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      12.512  -1.585   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.047   1.738   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.355   2.629   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.762  -0.535   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.194  -2.425   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.033  -2.696   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.493  -2.485   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.613  -4.122   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.668  -5.338   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.858  -5.127   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.383  -4.917   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.647  -3.602   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.068  -6.653   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.519   3.664   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      12.381   2.992   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      15.020  -2.491   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      14.497  -3.939   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      12.981  -4.210   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      11.988  -3.033   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      12.458  -5.659   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      16.536  -2.220   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      17.529  -3.397   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      17.006  -4.846   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      15.490  -5.117   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      17.998  -6.023   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      17.059  -0.771   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      18.575  -0.500   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      19.568  -1.678   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      19.045  -3.126   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      21.084  -1.407   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                                                       
CONECT    6    5    7   55                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   45                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   43                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   40                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   27                                                  
CONECT   17   16   12   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   27                                             
CONECT   22   21                                                            
CONECT   23   21   24   29                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   16   21   28                                             
CONECT   28   27                                                            
CONECT   29   23   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36                                                            
CONECT   40   13   41   42   43                                             
CONECT   41   40                                                            
CONECT   42   40                                                            
CONECT   43   40   10   44                                                  
CONECT   44   43                                                            
CONECT   45    8   46   50                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48   49                                                  
CONECT   48   47                                                            
CONECT   49   47                                                            
CONECT   50   45   51   55                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53   54                                                  
CONECT   53   52                                                            
CONECT   54   52                                                            
CONECT   55   50    6   56                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57                                                            
MASTER        0    0    0    0    0    0    0    0   59    0  126    0
END

View in JSmol

Synonyms

Value	Source
[3,4,5-Tris(acetyloxy)-6-{[14-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-5,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0,.0,]heptadec-7-en-4-yl]oxy}oxan-2-yl]methyl acetic acid	Generator
[3,4,5-Tris(acetyloxy)-6-{[14-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-5,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-4-yl]oxy}oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₄₄H₆₈O₁₅

Average Mass

837.0130 Da

Monoisotopic Mass

836.45582 Da

IUPAC Name

[3,4,5-tris(acetyloxy)-6-{[14-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-5,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-4-yl]oxy}oxan-2-yl]methyl acetate

Traditional Name

[3,4,5-tris(acetyloxy)-6-{[14-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-5,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-4-yl]oxy}oxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1OC(OC2CC3C(=CCC4C5(C)CC(O)C(C(C)(O)C(=O)CCC(C)(C)O)C5(C)CCC34C)C(C)(C)C2O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O

InChI Identifier

InChI=1S/C44H68O15/c1-22(45)54-21-30-33(55-23(2)46)34(56-24(3)47)35(57-25(4)48)38(59-30)58-29-19-27-26(40(7,8)37(29)51)13-14-31-41(27,9)17-18-42(10)36(28(49)20-43(31,42)11)44(12,53)32(50)15-16-39(5,6)52/h13,27-31,33-38,49,51-53H,14-21H2,1-12H3

InChI Key

UXHIMBDZUHTFOC-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
Picrorhiza kurrooa	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
Cucurbitacin skeleton
Triterpenoid
25-hydroxysteroid
22-oxosteroid
21-oxosteroid
20-hydroxysteroid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
Oxosteroid
16-hydroxysteroid
Delta-5-steroid
Tetracarboxylic acid or derivatives
O-glycosyl compound
Glycosyl compound
Acyloin
Oxane
Monosaccharide
Cyclic alcohol
Alpha-hydroxy ketone
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Ketone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Acetal
Organic oxygen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	3.54	ALOGPS
logP	2.43	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	12.87	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	221.65 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	209.97 m³·mol⁻¹	ChemAxon
Polarizability	90.18 Å³	ChemAxon
Number of Rings	5	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

14447026

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [3,4,5-tris(acetyloxy)-6-{[1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2,7-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}oxan-2-yl]methyl acetate (NP0204479)

MOL for NP0204479 ([3,4,5-tris(acetyloxy)-6-{[1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2,7-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}oxan-2-yl]methyl acetate)

3D MOL for NP0204479 ([3,4,5-tris(acetyloxy)-6-{[1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2,7-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}oxan-2-yl]methyl acetate)

3D SDF for NP0204479 ([3,4,5-tris(acetyloxy)-6-{[1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2,7-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}oxan-2-yl]methyl acetate)

3D-SDF for NP0204479 ([3,4,5-tris(acetyloxy)-6-{[1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2,7-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}oxan-2-yl]methyl acetate)

PDB for NP0204479 ([3,4,5-tris(acetyloxy)-6-{[1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2,7-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}oxan-2-yl]methyl acetate)

3D PDB for NP0204479 ([3,4,5-tris(acetyloxy)-6-{[1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2,7-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}oxan-2-yl]methyl acetate)

SMILES for NP0204479 ([3,4,5-tris(acetyloxy)-6-{[1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2,7-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}oxan-2-yl]methyl acetate)

INCHI for NP0204479 ([3,4,5-tris(acetyloxy)-6-{[1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2,7-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}oxan-2-yl]methyl acetate)

Structure for NP0204479 ([3,4,5-tris(acetyloxy)-6-{[1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2,7-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}oxan-2-yl]methyl acetate)

3D Structure for NP0204479 ([3,4,5-tris(acetyloxy)-6-{[1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2,7-dihydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,7h,8h,9h,9ah,10h,11h-cyclopenta[a]phenanthren-8-yl]oxy}oxan-2-yl]methyl acetate)