NP-MRD: Showing NP-Card for (-)-Khekadaengoside C (NP0075486)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 20:45:59 UTC

Updated at

2022-04-28 20:45:59 UTC

NP-MRD ID

NP0075486

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Khekadaengoside C

Description

(1R,2R,10R,11S,13R,14R,15R)-13-hydroxy-14-[(2R)-2-hydroxy-6-methyl-3-oxohept-6-en-2-yl]-1,6,6,11,15-pentamethyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-diene-5,17-dione belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions. (-)-Khekadaengoside C is found in Trichosanthes tricuspidata. Based on a literature review very few articles have been published on (1R,2R,10R,11S,13R,14R,15R)-13-hydroxy-14-[(2R)-2-hydroxy-6-methyl-3-oxohept-6-en-2-yl]-1,6,6,11,15-pentamethyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,7-diene-5,17-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282222462D          

 47 51  0  0  1  0            999 V2000
    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  2  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  1  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  1  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
    4.2663   -1.2846    0.0000 O   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  1  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  1  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
    1.3367    0.6509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  1  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
    0.8642   -2.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7703   -1.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5876   -1.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0939   -2.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8985   -1.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7109   -1.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083   -0.2865    0.0000 O   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
    2.8685    1.4085    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
    4.5466   -0.5086    0.0000 C   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
    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
    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
    6.7026   -0.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0466   -1.3344    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8587   -1.1892    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1390   -0.4133    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6072    0.2174    0.0000 C   0  0  2  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
    8.8875    0.9934    0.0000 C   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
    9.9511   -0.2681    0.0000 O   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
    7.7663   -2.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  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
  7 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
 12 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 17 25  1  1  0  0  0
 17 26  1  1  0  0  0
 15 27  1  6  0  0  0
 13 28  1  6  0  0  0
 12 29  1  1  0  0  0
  8 30  1  1  0  0  0
  4 31  1  0  0  0  0
 31 32  1  0  0  0  0
  1 32  1  0  0  0  0
 32 33  2  0  0  0  0
 31 34  1  0  0  0  0
 31 35  1  0  0  0  0
  1 36  1  0  0  0  0
 37 36  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 37 42  1  0  0  0  0
 41 43  1  6  0  0  0
 43 44  1  0  0  0  0
 40 45  1  1  0  0  0
 39 46  1  6  0  0  0
 38 47  1  1  0  0  0
M  END

     RDKit          3D

 99103  0  0  0  0  0  0  0  0999 V2000
    7.5707    2.6959    1.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1617    2.2224    0.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6082    1.7805    1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5628    2.0493   -0.3911 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0995    2.1602   -0.5645 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3432    1.1025    0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7886    1.4427    1.1875 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2566   -0.2992   -0.3148 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0190   -1.1341    0.6885 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1621   -0.3179   -1.4437 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9971   -0.7889   -0.8352 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0096   -2.2375   -1.2891 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6098   -2.2813   -2.5431 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -2.6452   -1.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7742   -1.3917   -1.1050 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8805   -0.5833   -2.4136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3757   -1.5563   -0.7294 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1624   -2.8644   -0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6537   -2.7166   -0.3778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2616   -1.5476   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6269   -0.2073   -0.4339 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3825    0.7095    0.4228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5767    0.4119    0.9772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2403    1.3195    1.7769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5266    1.8479    1.5324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4181    0.8025    1.5044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6971    1.1554    1.1133 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.5458   -0.0977    1.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5877   -0.6483    2.4301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6255    1.6135   -0.3263 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.8941    1.7745   -0.8791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8393    2.9003   -0.3324 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6824    3.2622   -1.6885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4928    2.6744    0.2860 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.9548    3.9208    0.6039 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1968   -0.8826    0.7428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0296   -1.4097    1.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7688   -1.5830   -0.5182 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3119   -2.9712   -0.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1515   -0.7677   -1.7332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2118   -0.4512    0.1096 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3753   -0.6853    1.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6690    0.7425   -0.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1533    1.7431   -0.6392 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1299    0.6312    0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7153   -0.7196   -0.0985 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8936   -1.5292    1.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1705    2.7387    2.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5619    3.0807    2.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5825    0.6723    1.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0386    2.1750    1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1453    2.1060    0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9308    1.0496   -0.8116 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0153    2.7646   -1.1698 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7909    2.0164   -1.6475 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6883    3.1603   -0.3148 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0745   -2.2022    0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7471   -0.8962    1.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1209   -0.8329    0.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6515    0.0460   -2.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125   -0.2176   -1.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4859   -2.9308   -0.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1846   -3.0532   -2.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2895   -3.4774   -0.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3303   -2.9773   -2.4090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5531   -1.0428   -3.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8639   -0.6907   -2.9155 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9769    0.4872   -2.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1689   -1.4655   -1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0307   -3.2117    0.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1496   -3.7048   -0.9669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2436   -3.6631   -0.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5371    0.1772   -1.4771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9682    1.6949    0.6337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7677    2.4938    2.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1386    1.9466    1.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5727    0.0735    0.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0769   -0.8485    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2925    0.0250    3.0750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0515    0.8681   -0.8997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2301    0.8609   -1.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4446    3.6793    0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3807    2.8261   -2.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8387    2.2519   -0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9671    3.9289    0.5103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9292   -3.4668   -1.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1305   -3.5175    0.3498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4163   -2.8761   -0.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5246   -1.1334   -2.5901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2218   -0.8485   -1.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8096    0.2842   -1.5660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2302    0.0987    2.0995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4228   -0.4916    1.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1020   -1.6365    1.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1897    0.8545    1.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5989    1.4647   -0.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8133   -2.1511    1.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9981   -0.8620    2.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0885   -2.2726    1.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  8 10  1  6
  8 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 27 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 23 36  1  0
 36 37  2  0
 36 38  1  0
 38 39  1  6
 38 40  1  0
 21 41  1  0
 41 42  1  1
 41 43  1  0
 43 44  2  0
 43 45  1  0
 45 46  1  0
 46 47  1  1
 46 11  1  0
 46 15  1  0
 41 17  1  0
 38 20  1  0
 34 25  1  0
  3 50  1  0
  3 51  1  0
  3 52  1  0
  1 48  1  0
  1 49  1  0
  4 53  1  0
  4 54  1  0
  5 55  1  0
  5 56  1  0
  9 57  1  0
  9 58  1  0
  9 59  1  0
 10 60  1  0
 11 61  1  6
 12 62  1  1
 13 63  1  0
 14 64  1  0
 14 65  1  0
 16 66  1  0
 16 67  1  0
 16 68  1  0
 17 69  1  6
 18 70  1  0
 18 71  1  0
 19 72  1  0
 21 73  1  6
 22 74  1  0
 25 75  1  1
 27 76  1  1
 28 77  1  0
 28 78  1  0
 29 79  1  0
 30 80  1  6
 31 81  1  0
 32 82  1  1
 33 83  1  0
 34 84  1  6
 35 85  1  0
 39 86  1  0
 39 87  1  0
 39 88  1  0
 40 89  1  0
 40 90  1  0
 40 91  1  0
 42 92  1  0
 42 93  1  0
 42 94  1  0
 45 95  1  0
 45 96  1  0
 47 97  1  0
 47 98  1  0
 47 99  1  0
M  END


  Mrv1652304282222462D          

 47 51  0  0  1  0            999 V2000
    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  2  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  1  0  0  0  0  0  0  0  0  0
    4.0148    0.1221    0.0000 C   0  0  1  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
    4.2663   -1.2846    0.0000 O   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  1  0  0  0  0  0  0  0  0  0
    2.6708    0.6076    0.0000 C   0  0  1  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
    1.3367    0.6509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5660   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0596   -0.7929    0.0000 C   0  0  1  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
    0.8642   -2.2084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2640   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7703   -1.9827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5876   -1.8698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0939   -2.5212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8985   -1.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7109   -1.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083   -0.2865    0.0000 O   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
    2.8685    1.4085    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
    4.5466   -0.5086    0.0000 C   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
    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
    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
    6.7026   -0.8489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5148   -0.7037    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0466   -1.3344    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.8587   -1.1892    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.1390   -0.4133    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6072    0.2174    0.0000 C   0  0  2  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
    8.8875    0.9934    0.0000 C   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
    9.9511   -0.2681    0.0000 O   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
    7.7663   -2.1103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  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
  7 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
 12 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 17 25  1  1  0  0  0
 17 26  1  1  0  0  0
 15 27  1  6  0  0  0
 13 28  1  6  0  0  0
 12 29  1  1  0  0  0
  8 30  1  1  0  0  0
  4 31  1  0  0  0  0
 31 32  1  0  0  0  0
  1 32  1  0  0  0  0
 32 33  2  0  0  0  0
 31 34  1  0  0  0  0
 31 35  1  0  0  0  0
  1 36  1  0  0  0  0
 37 36  1  6  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 37 42  1  0  0  0  0
 41 43  1  6  0  0  0
 43 44  1  0  0  0  0
 40 45  1  1  0  0  0
 39 46  1  6  0  0  0
 38 47  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0075486

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)CCC(=O)[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@H]3CC=C4[C@@H](C=C(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C36H52O11/c1-17(2)9-12-24(39)36(8,45)29-20(38)14-33(5)23-11-10-18-19(35(23,7)25(40)15-34(29,33)6)13-21(30(44)32(18,3)4)46-31-28(43)27(42)26(41)22(16-37)47-31/h10,13,19-20,22-23,26-29,31,37-38,41-43,45H,1,9,11-12,14-16H2,2-8H3/t19-,20-,22-,23-,26-,27+,28-,29+,31-,33+,34-,35+,36+/m1/s1

> <INCHI_KEY>
STJBLNHSRWHURW-KSIIBEFFSA-N

> <FORMULA>
C36H52O11

> <MOLECULAR_WEIGHT>
660.801

> <EXACT_MASS>
660.350962494

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
71.4763859041202

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,10R,11S,13R,14R,15R)-13-hydroxy-14-[(2R)-2-hydroxy-6-methyl-3-oxohept-6-en-2-yl]-1,6,6,11,15-pentamethyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-diene-5,17-dione

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
1.710794482333333

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.824291875796398

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.128584606666873

> <JCHEM_PKA_STRONGEST_BASIC>
-2.88358525593679

> <JCHEM_POLAR_SURFACE_AREA>
191.04999999999998

> <JCHEM_REFRACTIVITY>
172.87570000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,10R,11S,13R,14R,15R)-13-hydroxy-14-[(2R)-2-hydroxy-6-methyl-3-oxohept-6-en-2-yl]-1,6,6,11,15-pentamethyl-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7-diene-5,17-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.964  -2.398   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.978  -1.480   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.033  -2.696   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.613  -4.122   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.493  -2.485   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.438  -3.701   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.963  -3.490   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.909  -4.706   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.544  -2.064   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.194  -2.425   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.762  -0.535   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.047   1.738   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.355   2.629   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.831   3.743   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      12.191   3.252   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      12.512  -1.585   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      14.028  -1.314   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      15.020  -2.491   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      16.536  -2.220   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      17.059  -0.771   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      16.067   0.406   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      14.551   0.135   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      16.590   1.854   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      18.106   2.125   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      18.575  -0.500   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      17.529  -3.397   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      14.497  -3.939   0.000  0.00  0.00           O+0
CONECT    1    2   32   36                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   31                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    3    9   30                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   16   29                                             
CONECT   13   12    7   14   28                                             
CONECT   14   13   15                                                       
CONECT   15   14   16   27                                                  
CONECT   16   15   12   17                                                  
CONECT   17   16   18   25   26                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   17                                                            
CONECT   26   17                                                            
CONECT   27   15                                                            
CONECT   28   13                                                            
CONECT   29   12                                                            
CONECT   30    8                                                            
CONECT   31    4   32   34   35                                             
CONECT   32   31    1   33                                                  
CONECT   33   32                                                            
CONECT   34   31                                                            
CONECT   35   31                                                            
CONECT   36    1   37                                                       
CONECT   37   36   38   42                                                  
CONECT   38   37   39   47                                                  
CONECT   39   38   40   46                                                  
CONECT   40   39   41   45                                                  
CONECT   41   40   42   43                                                  
CONECT   42   41   37                                                       
CONECT   43   41   44                                                       
CONECT   44   43                                                            
CONECT   45   40                                                            
CONECT   46   39                                                            
CONECT   47   38                                                            
MASTER        0    0    0    0    0    0    0    0   47    0  102    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₆H₅₂O₁₁

Average Mass

660.8010 Da

Monoisotopic Mass

660.35096 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=C)CCC(=O)[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@H]3CC=C4[C@@H](C=C(O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C

InChI Identifier

InChI=1S/C36H52O11/c1-17(2)9-12-24(39)36(8,45)29-20(38)14-33(5)23-11-10-18-19(35(23,7)25(40)15-34(29,33)6)13-21(30(44)32(18,3)4)46-31-28(43)27(42)26(41)22(16-37)47-31/h10,13,19-20,22-23,26-29,31,37-38,41-43,45H,1,9,11-12,14-16H2,2-8H3/t19-,20-,22-,23-,26-,27+,28-,29+,31-,33+,34-,35+,36+/m1/s1

InChI Key

STJBLNHSRWHURW-KSIIBEFFSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cucurbitacins. These are polycyclic compounds containing the tetracyclic cucurbitane nucleus skeleton, 19-(10->9b)-abeo-10alanost-5-ene (also known as 9b-methyl-19-nor lanosta-5-ene), with a variety of oxygenation functionalities at different positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cucurbitacins

Direct Parent

Cucurbitacins

Alternative Parents

Substituents

Triterpenoid
Cucurbitacin skeleton
22-oxosteroid
21-oxosteroid
20-hydroxysteroid
14-alpha-methylsteroid
16-hydroxysteroid
16-alpha-hydroxysteroid
Oxosteroid
11-oxosteroid
Hydroxysteroid
3-oxosteroid
3-oxo-delta-1-steroid
Delta-1-steroid
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Cyclohexenone
Oxane
Monosaccharide
Acyloin
Tertiary alcohol
Cyclic alcohol
Alpha-hydroxy ketone
Cyclic ketone
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
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	2.24	ALOGPS
logP	1.71	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	12.13	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	191.05 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	172.88 m³·mol⁻¹	ChemAxon
Polarizability	71.48 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

154496837

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Khekadaengoside C (NP0075486)

MOL for NP0075486 ((-)-Khekadaengoside C)

3D MOL for NP0075486 ((-)-Khekadaengoside C)

3D SDF for NP0075486 ((-)-Khekadaengoside C)

3D-SDF for NP0075486 ((-)-Khekadaengoside C)

PDB for NP0075486 ((-)-Khekadaengoside C)

3D PDB for NP0075486 ((-)-Khekadaengoside C)

SMILES for NP0075486 ((-)-Khekadaengoside C)

INCHI for NP0075486 ((-)-Khekadaengoside C)

Structure for NP0075486 ((-)-Khekadaengoside C)

3D Structure for NP0075486 ((-)-Khekadaengoside C)