NP-MRD: Showing NP-Card for 8-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2-hydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione (NP0319750)

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Record Information

Version

2.0

Created at

2022-09-11 20:56:39 UTC

Updated at

2022-09-11 20:56:40 UTC

NP-MRD ID

NP0319750

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2-hydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione

Description

4-{[4,5-Dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-14-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-13-hydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-diene-5,17-dione 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. 8-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2-hydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione is found in Trichosanthes tricuspidata. 4-{[4,5-Dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-14-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-13-hydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-diene-5,17-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171509312D          

 58 63  0  0  0  0            999 V2000
   -1.9573   -4.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1452   -4.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6133   -3.8333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1988   -3.9785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7306   -3.3478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4503   -2.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618   -2.4267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8936   -3.0574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6421   -1.6508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4542   -1.5056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1103   -1.0201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3906   -0.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1412    0.3866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018   -1.1653    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9821   -1.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7942   -2.0864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261   -1.4557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1382   -1.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.7336    0.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1602   -0.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0886   -1.5240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6327   -3.4459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.0845   -3.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   10.1973   -3.9246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4662   -2.1482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5745   -2.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7624   -1.8914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4821   -1.1154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9503   -1.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8616    0.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0458   -0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2336   -0.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0527   -5.3852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3967   -5.8707    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  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 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
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
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 37 40  1  0  0  0  0
 29 41  1  0  0  0  0
 24 41  1  0  0  0  0
 41 42  1  0  0  0  0
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 17 51  1  0  0  0  0
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  4 53  1  0  0  0  0
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 55 57  1  0  0  0  0
  2 57  1  0  0  0  0
 57 58  1  0  0  0  0
M  END

     RDKit          3D

122127  0  0  0  0  0  0  0  0999 V2000
   -8.5188   -2.7764    3.2604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3460   -2.9438    1.7803 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.6681   -1.8659    1.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1817   -2.2510   -0.0481 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.5408   -1.1537   -0.6010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1981   -1.3392   -0.8136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9280   -1.0359   -2.2933 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2729   -2.0581   -3.1325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7238    0.2254   -2.5871 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5904    0.6503   -3.8836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3042    1.3312   -1.6437 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3767    2.4155   -1.7396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0860    3.5077   -0.9500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2403    0.9368   -0.3369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4879   -0.1855   -0.0735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1576   -0.1353   -0.4483 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2377    0.8135    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441    0.9120   -0.4664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0504    1.8596   -0.0046 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3089    2.4665    1.3300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6177    2.7768    2.2069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1008    2.5623    1.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3425    1.3099    0.0940 C   0  0  1  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004171509312D          

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M  END
> <DATABASE_ID>
NP0319750

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2C(O)C(O)C(CO)OC2OC2=CC3C(=CCC4C5(C)CC(O)C(C(C)(O)C(=O)CCC(C)(C)O)C5(C)CC(=O)C34C)C(C)(C)C2=O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C42H64O16/c1-18-27(47)29(49)31(51)35(55-18)58-32-30(50)28(48)23(17-43)57-36(32)56-22-14-20-19(38(4,5)34(22)52)10-11-24-39(6)15-21(44)33(40(39,7)16-26(46)41(20,24)8)42(9,54)25(45)12-13-37(2,3)53/h10,14,18,20-21,23-24,27-33,35-36,43-44,47-51,53-54H,11-13,15-17H2,1-9H3

> <INCHI_KEY>
UFINFGVQJXYBJL-UHFFFAOYSA-N

> <FORMULA>
C42H64O16

> <MOLECULAR_WEIGHT>
824.958

> <EXACT_MASS>
824.419435981

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
122

> <JCHEM_AVERAGE_POLARIZABILITY>
86.30420969438211

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-14-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-13-hydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-diene-5,17-dione

> <ALOGPS_LOGP>
1.54

> <JCHEM_LOGP>
-0.13660007066666674

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.575582209345214

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.042537980617658

> <JCHEM_PKA_STRONGEST_BASIC>
-2.883585152441264

> <JCHEM_POLAR_SURFACE_AREA>
270.2

> <JCHEM_REFRACTIVITY>
205.8039000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-14-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-13-hydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-diene-5,17-dione

> <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      -3.654  -8.062   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.138  -8.333   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.145  -7.156   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.371  -7.427   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.364  -6.249   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.841  -4.801   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.675  -4.530   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.668  -5.707   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.199  -3.081   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.715  -2.810   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.206  -1.904   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.729  -0.456   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.264   0.722   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.310  -2.175   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       1.833  -3.624   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.349  -3.895   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.342  -2.717   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.858  -2.988   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.851  -1.811   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.327  -0.363   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.320   0.815   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.836   0.544   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.359  -0.905   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.875  -1.176   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.506   0.319   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.091  -0.231   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.366  -1.095   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      14.814  -0.572   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      12.938  -2.574   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.883  -3.790   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      15.099  -2.845   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      12.667  -4.735   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      14.828  -5.006   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      14.248  -6.432   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      16.354  -4.795   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      17.299  -6.011   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      18.824  -5.800   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      20.350  -5.590   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      18.614  -4.275   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      19.035  -7.326   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      11.399  -2.624   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      12.070  -4.010   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      10.406  -3.802   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       8.890  -3.531   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       7.897  -4.708   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       8.367  -2.082   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       7.374  -3.259   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       4.811  -0.092   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       5.342   1.354   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       3.480   0.682   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       3.819  -1.269   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       2.303  -0.998   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       0.894  -8.875   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       2.410  -9.146   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -0.098 -10.052   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       0.425 -11.501   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      -1.614  -9.781   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      -2.607 -10.959   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   57                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   53                                                  
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   51                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   46                                                  
CONECT   20   19   21   48                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   46                                                  
CONECT   24   23   25   26   41                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   41                                                  
CONECT   30   29   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39   40                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   37                                                            
CONECT   41   29   24   42   43                                             
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   19   23   47                                             
CONECT   47   46                                                            
CONECT   48   20   49   50   51                                             
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51   48   17   52                                                  
CONECT   52   51                                                            
CONECT   53    4   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   56   57                                                  
CONECT   56   55                                                            
CONECT   57   55    2   58                                                  
CONECT   58   57                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  126    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₆₄O₁₆

Average Mass

824.9580 Da

Monoisotopic Mass

824.41944 Da

IUPAC Name

4-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-14-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-13-hydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,7-diene-5,17-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1OC(OC2C(O)C(O)C(CO)OC2OC2=CC3C(=CCC4C5(C)CC(O)C(C(C)(O)C(=O)CCC(C)(C)O)C5(C)CC(=O)C34C)C(C)(C)C2=O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C42H64O16/c1-18-27(47)29(49)31(51)35(55-18)58-32-30(50)28(48)23(17-43)57-36(32)56-22-14-20-19(38(4,5)34(22)52)10-11-24-39(6)15-21(44)33(40(39,7)16-26(46)41(20,24)8)42(9,54)25(45)12-13-37(2,3)53/h10,14,18,20-21,23-24,27-33,35-36,43-44,47-51,53-54H,11-13,15-17H2,1-9H3

InChI Key

UFINFGVQJXYBJL-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
Trichosanthes tricuspidata	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
Triterpenoid
Cucurbitacin skeleton
25-hydroxysteroid
22-oxosteroid
21-oxosteroid
20-hydroxysteroid
16-hydroxysteroid
3-oxosteroid
Oxosteroid
3-oxo-delta-1-steroid
11-oxosteroid
Hydroxysteroid
Delta-1-steroid
Disaccharide
Glycosyl compound
O-glycosyl compound
Cyclohexenone
Oxane
Acyloin
Alpha-hydroxy ketone
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Cyclic ketone
Ketone
Acetal
Organoheterocyclic compound
Oxacycle
Polyol
Primary alcohol
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Hydrocarbon derivative
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	1.54	ALOGPS
logP	-0.14	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.04	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	270.2 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	205.8 m³·mol⁻¹	ChemAxon
Polarizability	86.3 Å³	ChemAxon
Number of Rings	6	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

73157161

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2-hydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione (NP0319750)

MOL for NP0319750 (8-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2-hydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D MOL for NP0319750 (8-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2-hydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D SDF for NP0319750 (8-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2-hydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D-SDF for NP0319750 (8-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2-hydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

PDB for NP0319750 (8-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2-hydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D PDB for NP0319750 (8-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2-hydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

SMILES for NP0319750 (8-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2-hydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

INCHI for NP0319750 (8-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2-hydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

Structure for NP0319750 (8-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2-hydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)

3D Structure for NP0319750 (8-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-1-(2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl)-2-hydroxy-3a,6,6,9b,11a-pentamethyl-1h,2h,3h,3bh,4h,9ah,11h-cyclopenta[a]phenanthrene-7,10-dione)