NP-MRD: Showing NP-Card for 16-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione (NP0211833)

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Record Information

Version

2.0

Created at

2022-09-05 10:16:23 UTC

Updated at

2022-09-05 10:16:23 UTC

NP-MRD ID

NP0211833

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione

Description

16-{[3,4-Dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]Henicosa-15,19-diene-12,17-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. 16-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione is found in Bryonia alba. 16-{[3,4-Dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]Henicosa-15,19-diene-12,17-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171507312D          

 56 62  0  0  0  0            999 V2000
    1.7476   -8.7355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5681   -8.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0525   -8.1533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8731   -8.2389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3575   -7.5711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0213   -6.8177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2008   -6.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7164   -7.3999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8646   -5.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0441   -5.8930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3491   -5.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0129   -4.5574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4973   -3.8896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3179   -3.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8023   -3.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4661   -2.5540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9505   -1.8862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7711   -1.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1072   -2.7252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9278   -2.8108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6722   -2.0264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5404   -2.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2552   -2.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0397   -2.4147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6532   -2.9662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4823   -3.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6978   -4.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0857   -4.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0481   -4.5373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0843   -3.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2639   -3.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6770   -4.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7795   -4.2320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9590   -4.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4746   -4.8142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6228   -3.3930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1384   -4.0608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4376   -2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0511   -3.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8355   -3.0067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8802   -4.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6456   -2.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8724   -1.6752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9038   -2.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1612   -3.1362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3406   -3.0506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1696   -5.3964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5057   -6.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3263   -6.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6624   -6.9889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2092   -8.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0297   -9.0779    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7248   -9.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0609  -10.4135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9042   -9.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198  -10.2423    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
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 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
 25 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
 27 30  1  0  0  0  0
 23 30  1  0  0  0  0
 30 31  1  0  0  0  0
 20 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 15 36  1  0  0  0  0
 19 36  1  0  0  0  0
 36 37  1  0  0  0  0
 25 38  1  0  0  0  0
 38 39  2  0  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 16 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
 42 45  1  0  0  0  0
 13 45  1  0  0  0  0
 45 46  2  0  0  0  0
 11 47  1  0  0  0  0
 47 48  1  0  0  0  0
  6 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
  4 51  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 55  1  0  0  0  0
  2 55  1  0  0  0  0
 55 56  1  0  0  0  0
M  END

     RDKit          3D

118124  0  0  0  0  0  0  0  0999 V2000
  -10.7195   -0.8553   -2.0862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3932   -1.4393   -2.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4065   -1.9603   -3.9326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3750   -1.4399   -1.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0163   -1.9539   -1.9611 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.6727   -2.9445   -0.8689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3712   -2.2915    0.4546 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.6744   -2.4128    1.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4574   -3.1389    1.0822 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9747   -0.8838    0.3137 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8148   -0.2833   -1.0249 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3677    0.3050   -1.0408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3436    0.8003    0.3792 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3555    1.8992    0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0163    1.3413    0.8053 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5860    2.5716    0.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3502    3.0731    0.6842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5461    2.3286    1.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8017    0.9222    1.6925 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4796    0.1497    1.4793 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6068    0.6658    1.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7914    0.0239    1.7745 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8147    0.1371    0.8722 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4538   -0.0986   -0.4568 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5734   -0.5942   -1.1215 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3228   -0.7269   -2.6084 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4585   -1.2198   -3.2458 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7970    0.2609   -0.8796 C   0  0  2  0  0  0  0  0  0  0  0  0
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    7.8980   -0.5234   -0.3063 C   0  0  1  0  0  0  0  0  0  0  0  0
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   10.0575    0.1356   -0.2409 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1305    0.8747    0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5902   -1.2655   -0.4510 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.5791   -1.1828   -1.4304 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5466   -2.2170   -0.9281 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2607   -1.9677   -2.2689 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.3281    1.5991   -0.4125 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4301    2.4101   -0.1595 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6133    1.4086    0.9192 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6403    1.2673    1.8802 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5720    1.9634    2.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2746    2.1856    3.6421 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860    2.9925    2.0288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3514    3.8222    0.9826 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2036    3.8682    3.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8748    0.3808    0.7618 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.4730   -1.6069    1.8811 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1402   -0.1488    2.5451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0364   -1.0220   -2.1227 O   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.0608   -2.8843   -3.9482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8844   -1.2358   -4.6348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5441   -1.0056   -0.7181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0793   -2.5405   -2.9311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4540   -3.7070   -0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7833   -3.5370   -1.2389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4758   -2.9143    0.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5140   -3.0824    2.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0311   -1.4224    1.5669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8351   -3.6041    1.8673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8178   -0.3124    0.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5122    0.6273   -1.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3158    1.0911   -1.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7468   -0.5640   -1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4135    2.4431   -0.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0363    2.7007    1.2006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3870    1.5885    0.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1389    1.6484    1.8888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5295    2.4526   -1.0199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3452    3.4140    0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0960    4.1354    0.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422    0.7680    2.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5540   -0.6878    1.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7468   -1.6347   -0.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9191   -1.8099   -2.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1533004171507312D          

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M  END
> <DATABASE_ID>
NP0211833

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC2C(CO)OC(OC3=CC4C(=CCC5C6(C)CC7OC(CC(C)(O)C7C6(C)CC(=O)C45C)C=C(C)C)C(C)(C)C3=O)C(O)C2O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C42H62O14/c1-18(2)12-20-14-41(8,51)34-24(53-20)15-39(6)26-11-10-21-22(42(26,9)27(44)16-40(34,39)7)13-23(35(50)38(21,4)5)54-37-32(49)30(47)33(25(17-43)55-37)56-36-31(48)29(46)28(45)19(3)52-36/h10,12-13,19-20,22,24-26,28-34,36-37,43,45-49,51H,11,14-17H2,1-9H3

> <INCHI_KEY>
JWSFCGPOADZMNW-UHFFFAOYSA-N

> <FORMULA>
C42H62O14

> <MOLECULAR_WEIGHT>
790.944

> <EXACT_MASS>
790.413956676

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
118

> <JCHEM_AVERAGE_POLARIZABILITY>
85.06683257173081

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
1.2984095336666654

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.491225494938721

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.940323581854527

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9760429698901945

> <JCHEM_POLAR_SURFACE_AREA>
221.89999999999995

> <JCHEM_REFRACTIVITY>
202.24040000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-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       3.262 -16.306   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.794 -16.466   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.698 -15.219   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       7.230 -15.379   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.134 -14.133   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.506 -12.726   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.975 -12.567   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.071 -13.813   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.347 -11.160   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.816 -11.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.252  -9.914   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.624  -8.507   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.528  -7.261   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.060  -7.420   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.964  -6.174   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.337  -4.767   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.241  -3.521   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.773  -3.681   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.400  -5.087   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.932  -5.247   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.455  -3.783   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.075  -4.215   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.410  -4.984   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      16.874  -4.507   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      18.019  -5.537   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.700  -7.044   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.236  -7.521   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.960  -8.880   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      15.023  -8.470   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      15.091  -6.491   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.559  -6.653   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.330  -7.986   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.655  -7.900   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      11.123  -7.740   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.219  -8.987   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      10.496  -6.334   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.592  -7.580   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      19.484  -5.060   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      20.629  -6.090   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      22.093  -5.613   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      20.310  -7.596   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.805  -4.608   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       7.228  -3.127   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.420  -3.934   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       5.901  -5.854   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       4.369  -5.694   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       7.783 -10.073   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       8.411 -11.480   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       9.942 -11.640   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      10.570 -13.046   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       7.857 -16.786   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       9.389 -16.945   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       6.953 -18.032   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       7.580 -19.439   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       5.421 -17.872   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       4.517 -19.119   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   55                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   51                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   48                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   47                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   45                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   36                                                  
CONECT   16   15   17   42                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   36                                                  
CONECT   20   19   21   22   31                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   38                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   23   31                                                  
CONECT   31   30   20   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   15   19   37                                             
CONECT   37   36                                                            
CONECT   38   25   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39                                                            
CONECT   42   16   43   44   45                                             
CONECT   43   42                                                            
CONECT   44   42                                                            
CONECT   45   42   13   46                                                  
CONECT   46   45                                                            
CONECT   47   11   48                                                       
CONECT   48   47    6   49                                                  
CONECT   49   48   50                                                       
CONECT   50   49                                                            
CONECT   51    4   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53    2   56                                                  
CONECT   56   55                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  124    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₂H₆₂O₁₄

Average Mass

790.9440 Da

Monoisotopic Mass

790.41396 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

CC1OC(OC2C(CO)OC(OC3=CC4C(=CCC5C6(C)CC7OC(CC(C)(O)C7C6(C)CC(=O)C45C)C=C(C)C)C(C)(C)C3=O)C(O)C2O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C42H62O14/c1-18(2)12-20-14-41(8,51)34-24(53-20)15-39(6)26-11-10-21-22(42(26,9)27(44)16-40(34,39)7)13-23(35(50)38(21,4)5)54-37-32(49)30(47)33(25(17-43)55-37)56-36-31(48)29(46)28(45)19(3)52-36/h10,12-13,19-20,22,24-26,28-34,36-37,43,45-49,51H,11,14-17H2,1-9H3

InChI Key

JWSFCGPOADZMNW-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
Bryonia alba	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
Diterpene glycoside
20-hydroxysteroid
Diterpenoid
3-oxo-delta-1-steroid
3-oxosteroid
Hydroxysteroid
11-oxosteroid
Oxosteroid
Delta-1-steroid
Terpene glycoside
Disaccharide
Glycosyl compound
O-glycosyl compound
Cyclohexenone
Oxane
Tertiary alcohol
Secondary alcohol
Ketone
Cyclic ketone
Polyol
Acetal
Dialkyl ether
Oxacycle
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
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	2.14	ALOGPS
logP	1.3	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	11.94	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	221.9 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	202.24 m³·mol⁻¹	ChemAxon
Polarizability	85.07 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione (NP0211833)

MOL for NP0211833 (16-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

3D MOL for NP0211833 (16-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

3D SDF for NP0211833 (16-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

3D-SDF for NP0211833 (16-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

PDB for NP0211833 (16-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

3D PDB for NP0211833 (16-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

SMILES for NP0211833 (16-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

INCHI for NP0211833 (16-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

Structure for NP0211833 (16-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)

3D Structure for NP0211833 (16-{[3,4-dihydroxy-6-(hydroxymethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-8-hydroxy-2,8,10,13,18,18-hexamethyl-6-(2-methylprop-1-en-1-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-15,19-diene-12,17-dione)