NP-MRD: Showing NP-Card for xestosaprol D (NP0039753)

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Record Information

Version

2.0

Created at

2021-06-20 22:05:38 UTC

Updated at

2021-06-30 00:13:16 UTC

NP-MRD ID

NP0039753

Secondary Accession Numbers

None

Natural Product Identification

Common Name

xestosaprol D

Provided By

JEOL Database JEOL Logo

Description

xestosaprol D is found in Xestospongia sp. xestosaprol D was first documented in 2010 (Millan-Aguinaga, M., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100053D          

 42 46  0  0  0  0            999 V2000
    2.5965    0.4781    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3320   -0.3664    0.2181 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7208   -1.8262   -0.1741 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2989   -2.6313    1.0205 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3561   -2.7266    2.2415 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5342   -1.5002    2.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789   -1.1372    3.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196    0.0194    3.0237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5054    0.3862    1.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5019   -0.4615    1.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332    1.4299    0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8068    2.3115    1.3471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5773    1.3011   -0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2570    2.0502   -1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9196    1.9240   -2.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1095    1.0574   -3.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7815    0.3006   -2.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4651    0.3994   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4626    0.9052   -4.6207 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8517    0.6243   -4.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449    2.1788   -5.3964 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3116    2.5641   -5.2209 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6826    2.7130   -3.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6240    3.4200   -3.4166 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2402    0.5188   -0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1921    0.0792    1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3438    1.5122    0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4602   -1.8243   -0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -2.3595   -0.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -3.6442    0.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2430   -2.1720    1.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6798   -3.5783    2.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9410   -2.9271    3.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7166   -1.5865    4.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0619    2.7220   -1.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5899   -0.3550   -2.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0985    0.0551   -5.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0382    0.5354   -5.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3728    2.0385   -6.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7949    2.9963   -5.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9722    1.8124   -5.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4910    3.5219   -5.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
 18  2  1  0  0  0  0
  9 11  1  0  0  0  0
 10  2  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 16 15  1  0  0  0  0
 16 19  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
 10  6  1  0  0  0  0
 15 23  1  0  0  0  0
 23 22  1  0  0  0  0
 22 21  1  0  0  0  0
 21 19  1  0  0  0  0
 13 18  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 13 14  1  0  0  0  0
 11 12  2  0  0  0  0
 14 15  2  0  0  0  0
  2  1  1  1  0  0  0
 23 24  2  0  0  0  0
 13 11  1  0  0  0  0
 19 20  1  0  0  0  0
 14 35  1  0  0  0  0
 17 36  1  0  0  0  0
 22 41  1  0  0  0  0
 22 42  1  0  0  0  0
 21 39  1  0  0  0  0
 21 40  1  0  0  0  0
 19 37  1  6  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  7 34  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 20 38  1  0  0  0  0
M  END

     RDKit          3D

 42 46  0  0  0  0  0  0  0  0999 V2000
    2.5965    0.4781    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3320   -0.3664    0.2181 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7208   -1.8262   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2989   -2.6313    1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561   -2.7266    2.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5342   -1.5002    2.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789   -1.1372    3.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196    0.0194    3.0237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5054    0.3862    1.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5019   -0.4615    1.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332    1.4299    0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8068    2.3115    1.3471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5773    1.3011   -0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2570    2.0502   -1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9196    1.9240   -2.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1095    1.0574   -3.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7815    0.3006   -2.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4651    0.3994   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4626    0.9052   -4.6207 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8517    0.6243   -4.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449    2.1788   -5.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116    2.5641   -5.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826    2.7130   -3.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6240    3.4200   -3.4166 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2402    0.5188   -0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1921    0.0792    1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3438    1.5122    0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4602   -1.8243   -0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -2.3595   -0.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -3.6442    0.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2430   -2.1720    1.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6798   -3.5783    2.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9410   -2.9271    3.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7166   -1.5865    4.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0619    2.7220   -1.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5899   -0.3550   -2.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0985    0.0551   -5.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0382    0.5354   -5.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3728    2.0385   -6.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7949    2.9963   -5.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9722    1.8124   -5.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4910    3.5219   -5.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
 18  2  1  0
  9 11  1  0
 10  2  1  0
 16 17  2  0
 17 18  1  0
 16 15  1  0
 16 19  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
 10  6  1  0
 15 23  1  0
 23 22  1  0
 22 21  1  0
 21 19  1  0
 13 18  2  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 13 14  1  0
 11 12  2  0
 14 15  2  0
  2  1  1  1
 23 24  2  0
 13 11  1  0
 19 20  1  0
 14 35  1  0
 17 36  1  0
 22 41  1  0
 22 42  1  0
 21 39  1  0
 21 40  1  0
 19 37  1  6
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  7 34  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 20 38  1  0
M  END


  Mrv1652306212100053D          

 42 46  0  0  0  0            999 V2000
    2.5965    0.4781    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3320   -0.3664    0.2181 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7208   -1.8262   -0.1741 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2989   -2.6313    1.0205 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3561   -2.7266    2.2415 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5342   -1.5002    2.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789   -1.1372    3.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196    0.0194    3.0237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5054    0.3862    1.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5019   -0.4615    1.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332    1.4299    0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8068    2.3115    1.3471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5773    1.3011   -0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2570    2.0502   -1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9196    1.9240   -2.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1095    1.0574   -3.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7815    0.3006   -2.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4651    0.3994   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4626    0.9052   -4.6207 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8517    0.6243   -4.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449    2.1788   -5.3964 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3116    2.5641   -5.2209 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6826    2.7130   -3.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6240    3.4200   -3.4166 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2402    0.5188   -0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1921    0.0792    1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3438    1.5122    0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4602   -1.8243   -0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -2.3595   -0.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -3.6442    0.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2430   -2.1720    1.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6798   -3.5783    2.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9410   -2.9271    3.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7166   -1.5865    4.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0619    2.7220   -1.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5899   -0.3550   -2.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0985    0.0551   -5.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0382    0.5354   -5.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3728    2.0385   -6.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7949    2.9963   -5.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9722    1.8124   -5.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4910    3.5219   -5.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
 18  2  1  0  0  0  0
  9 11  1  0  0  0  0
 10  2  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 16 15  1  0  0  0  0
 16 19  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
 10  6  1  0  0  0  0
 15 23  1  0  0  0  0
 23 22  1  0  0  0  0
 22 21  1  0  0  0  0
 21 19  1  0  0  0  0
 13 18  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 13 14  1  0  0  0  0
 11 12  2  0  0  0  0
 14 15  2  0  0  0  0
  2  1  1  1  0  0  0
 23 24  2  0  0  0  0
 13 11  1  0  0  0  0
 19 20  1  0  0  0  0
 14 35  1  0  0  0  0
 17 36  1  0  0  0  0
 22 41  1  0  0  0  0
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 21 39  1  0  0  0  0
 21 40  1  0  0  0  0
 19 37  1  6  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  7 34  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 20 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0039753

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C2=C([H])C3=C(C([H])=C2C(=O)C([H])([H])C1([H])[H])C(=O)C1=C2C(=C([H])O1)C([H])([H])C([H])([H])C([H])([H])[C@@]32C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O4/c1-20-6-2-3-10-9-24-19(17(10)20)18(23)13-7-11-12(8-14(13)20)16(22)5-4-15(11)21/h7-9,16,22H,2-6H2,1H3/t16-,20+/m1/s1

> <INCHI_KEY>
PWKVGKRTNJJKTQ-UZLBHIALSA-N

> <FORMULA>
C20H18O4

> <MOLECULAR_WEIGHT>
322.36

> <EXACT_MASS>
322.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
34.695888683171475

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R)-5-hydroxy-1-methyl-14-oxapentacyclo[11.6.1.0^{2,11}.0^{4,9}.0^{16,20}]icosa-2(11),3,9,13(20),15-pentaene-8,12-dione

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
2.7697918616666666

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.662106032860564

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.040140314469507

> <JCHEM_PKA_STRONGEST_BASIC>
-2.890260975007353

> <JCHEM_POLAR_SURFACE_AREA>
67.50999999999999

> <JCHEM_REFRACTIVITY>
99.84589999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R)-5-hydroxy-1-methyl-14-oxapentacyclo[11.6.1.0^{2,11}.0^{4,9}.0^{16,20}]icosa-2(11),3,9,13(20),15-pentaene-8,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 42 46  0  0  0  0  0  0  0  0999 V2000
    2.5965    0.4781    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3320   -0.3664    0.2181 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7208   -1.8262   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2989   -2.6313    1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561   -2.7266    2.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5342   -1.5002    2.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789   -1.1372    3.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196    0.0194    3.0237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5054    0.3862    1.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5019   -0.4615    1.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332    1.4299    0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8068    2.3115    1.3471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5773    1.3011   -0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2570    2.0502   -1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9196    1.9240   -2.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1095    1.0574   -3.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7815    0.3006   -2.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4651    0.3994   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4626    0.9052   -4.6207 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8517    0.6243   -4.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449    2.1788   -5.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116    2.5641   -5.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826    2.7130   -3.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6240    3.4200   -3.4166 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2402    0.5188   -0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1921    0.0792    1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3438    1.5122    0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4602   -1.8243   -0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -2.3595   -0.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -3.6442    0.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2430   -2.1720    1.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6798   -3.5783    2.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9410   -2.9271    3.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7166   -1.5865    4.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0619    2.7220   -1.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5899   -0.3550   -2.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0985    0.0551   -5.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0382    0.5354   -5.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3728    2.0385   -6.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7949    2.9963   -5.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9722    1.8124   -5.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4910    3.5219   -5.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
 18  2  1  0
  9 11  1  0
 10  2  1  0
 16 17  2  0
 17 18  1  0
 16 15  1  0
 16 19  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
 10  6  1  0
 15 23  1  0
 23 22  1  0
 22 21  1  0
 21 19  1  0
 13 18  2  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 13 14  1  0
 11 12  2  0
 14 15  2  0
  2  1  1  1
 23 24  2  0
 13 11  1  0
 19 20  1  0
 14 35  1  0
 17 36  1  0
 22 41  1  0
 22 42  1  0
 21 39  1  0
 21 40  1  0
 19 37  1  6
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  7 34  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 20 38  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       2.596   0.478   0.485  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.332  -0.366   0.218  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.721  -1.826  -0.174  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.299  -2.631   1.020  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.356  -2.727   2.241  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.534  -1.500   2.408  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.379  -1.137   3.376  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.020   0.019   3.024  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.505   0.386   1.821  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.502  -0.462   1.450  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.033   1.430   0.996  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.807   2.312   1.347  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.577   1.301  -0.436  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.257   2.050  -1.405  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.920   1.924  -2.757  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.110   1.057  -3.158  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.782   0.301  -2.179  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.465   0.399  -0.809  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.463   0.905  -4.621  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.852   0.624  -4.761  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.145   2.179  -5.396  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.312   2.564  -5.221  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.683   2.713  -3.764  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.624   3.420  -3.417  0.00  0.00           O+0
HETATM   25  H   UNK     0       3.240   0.519  -0.401  0.00  0.00           H+0
HETATM   26  H   UNK     0       3.192   0.079   1.313  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.344   1.512   0.752  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.460  -1.824  -0.984  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.839  -2.360  -0.556  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.555  -3.644   0.688  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.243  -2.172   1.337  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.680  -3.578   2.097  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.941  -2.927   3.146  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.717  -1.587   4.300  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.062   2.722  -1.105  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.590  -0.355  -2.502  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.099   0.055  -5.027  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.038   0.535  -5.712  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.373   2.038  -6.460  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.795   2.996  -5.055  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.972   1.812  -5.667  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.491   3.522  -5.721  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2   18   10    3    1                                             
CONECT    3    2    4   28   29                                             
CONECT    4    3    5   30   31                                             
CONECT    5    4    6   32   33                                             
CONECT    6    5   10    7                                                  
CONECT    7    6    8   34                                                  
CONECT    8    7    9                                                       
CONECT    9   11    8   10                                                  
CONECT   10    2    6    9                                                  
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   18   14   11                                                  
CONECT   14   13   15   35                                                  
CONECT   15   16   23   14                                                  
CONECT   16   17   15   19                                                  
CONECT   17   16   18   36                                                  
CONECT   18    2   17   13                                                  
CONECT   19   16   21   20   37                                             
CONECT   20   19   38                                                       
CONECT   21   22   19   39   40                                             
CONECT   22   23   21   41   42                                             
CONECT   23   15   22   24                                                  
CONECT   24   23                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    3                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    5                                                            
CONECT   34    7                                                            
CONECT   35   14                                                            
CONECT   36   17                                                            
CONECT   37   19                                                            
CONECT   38   20                                                            
CONECT   39   21                                                            
CONECT   40   21                                                            
CONECT   41   22                                                            
CONECT   42   22                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

RDKit          3D

42 46  0  0  0  0  0  0  0  0999 V2000
    2.5965    0.4781    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3320   -0.3664    0.2181 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7208   -1.8262   -0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2989   -2.6313    1.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561   -2.7266    2.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5342   -1.5002    2.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3789   -1.1372    3.3762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196    0.0194    3.0237 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5054    0.3862    1.8205 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5019   -0.4615    1.4503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0332    1.4299    0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8068    2.3115    1.3471 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5773    1.3011   -0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2570    2.0502   -1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9196    1.9240   -2.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1095    1.0574   -3.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7815    0.3006   -2.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4651    0.3994   -0.8089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4626    0.9052   -4.6207 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8517    0.6243   -4.7614 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449    2.1788   -5.3964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3116    2.5641   -5.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6826    2.7130   -3.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6240    3.4200   -3.4166 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2402    0.5188   -0.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1921    0.0792    1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3438    1.5122    0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4602   -1.8243   -0.9840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -2.3595   -0.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -3.6442    0.6875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2430   -2.1720    1.3371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6798   -3.5783    2.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9410   -2.9271    3.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7166   -1.5865    4.3001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0619    2.7220   -1.1055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5899   -0.3550   -2.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0985    0.0551   -5.0269 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0382    0.5354   -5.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3728    2.0385   -6.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7949    2.9963   -5.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9722    1.8124   -5.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4910    3.5219   -5.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
 18  2  1  0
  9 11  1  0
 10  2  1  0
 16 17  2  0
 17 18  1  0
 16 15  1  0
 16 19  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
 10  6  1  0
 15 23  1  0
 23 22  1  0
 22 21  1  0
 21 19  1  0
 13 18  2  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 13 14  1  0
 11 12  2  0
 14 15  2  0
  2  1  1  1
 23 24  2  0
 13 11  1  0
 19 20  1  0
 14 35  1  0
 17 36  1  0
 22 41  1  0
 22 42  1  0
 21 39  1  0
 21 40  1  0
 19 37  1  6
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  7 34  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 20 38  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈O₄

Average Mass

322.3600 Da

Monoisotopic Mass

322.12051 Da

IUPAC Name

(1S,5R)-5-hydroxy-1-methyl-14-oxapentacyclo[11.6.1.0^{2,11}.0^{4,9}.0^{16,20}]icosa-2(11),3,9,13(20),15-pentaene-8,12-dione

Traditional Name

(1S,5R)-5-hydroxy-1-methyl-14-oxapentacyclo[11.6.1.0^{2,11}.0^{4,9}.0^{16,20}]icosa-2(11),3,9,13(20),15-pentaene-8,12-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C2=C([H])C3=C(C([H])=C2C(=O)C([H])([H])C1([H])[H])C(=O)C1=C2C(=C([H])O1)C([H])([H])C([H])([H])C([H])([H])[C@@]32C([H])([H])[H]

InChI Identifier

InChI=1S/C20H18O4/c1-20-6-2-3-10-9-24-19(17(10)20)18(23)13-7-11-12(8-14(13)20)16(22)5-4-15(11)21/h7-9,16,22H,2-6H2,1H3/t16-,20+/m1/s1

InChI Key

PWKVGKRTNJJKTQ-UZLBHIALSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Xestospongia sp.	JEOL database	Millan-Aguinaga, M., et al, Tetrahedron Lett. 51, 751 (2010)

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.03	ALOGPS
logP	2.77	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	14.04	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	67.51 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	99.85 m³·mol⁻¹	ChemAxon
Polarizability	34.7 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Millan-Aguinaga, M., et al. (2010). Millan-Aguinaga, M., et al, Tetrahedron Lett. 51, 751 (2010). Tetrahedron Lett.

Showing NP-Card for xestosaprol D (NP0039753)

MOL for NP0039753 (xestosaprol D)

3D MOL for NP0039753 (xestosaprol D)

3D SDF for NP0039753 (xestosaprol D)

3D-SDF for NP0039753 (xestosaprol D)

PDB for NP0039753 (xestosaprol D)

3D PDB for NP0039753 (xestosaprol D)

SMILES for NP0039753 (xestosaprol D)

INCHI for NP0039753 (xestosaprol D)

Structure for NP0039753 (xestosaprol D)

3D Structure for NP0039753 (xestosaprol D)