NP-MRD: Showing NP-Card for (1s,5s,7s,9s,10s,11s,15s,17s,19s,20s)-10,20-dimethyl-5,15-bis[(1s,2s)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1⁷,¹¹]docosane-3,13-dione (NP0269936)

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Record Information

Version

2.0

Created at

2022-09-08 15:34:09 UTC

Updated at

2022-09-08 15:34:09 UTC

NP-MRD ID

NP0269936

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,5s,7s,9s,10s,11s,15s,17s,19s,20s)-10,20-dimethyl-5,15-bis[(1s,2s)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1⁷,¹¹]docosane-3,13-dione

Description

Clavosolide A belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. (1s,5s,7s,9s,10s,11s,15s,17s,19s,20s)-10,20-dimethyl-5,15-bis[(1s,2s)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1⁷,¹¹]docosane-3,13-dione is found in Stelletta clavosa. (1s,5s,7s,9s,10s,11s,15s,17s,19s,20s)-10,20-dimethyl-5,15-bis[(1s,2s)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1⁷,¹¹]docosane-3,13-dione was first documented in 2015 (PMID: 26553131). Based on a literature review a small amount of articles have been published on Clavosolide A (PMID: 31166641) (PMID: 27455048) (PMID: 26766494) (PMID: 26236051).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082217342D          

 60 66  0  0  1  0            999 V2000
   -3.3979   -4.2980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5736   -4.3310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328   -3.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3085   -3.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8678   -2.9691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2514   -2.2388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8106   -1.5413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0137   -1.5743    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4544   -0.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2788   -0.9099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7718   -0.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4755    0.3769    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1905    1.1511    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5566    1.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3308    1.9641    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8588    2.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2904    0.5054    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0925    0.3122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4384    1.0612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7596   -0.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1901   -0.8769    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7494   -1.5743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1330   -2.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9573   -2.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3981   -1.6403    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.2224   -1.6733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6060   -2.4037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4304   -2.4367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8140   -3.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3732   -3.8645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7568   -4.5949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5812   -4.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5489   -3.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2838   -4.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3409   -3.0681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9002   -3.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0145   -0.9099    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.4552   -0.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6400   -3.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9363   -3.5916    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2213   -4.3658    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8552   -4.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0810   -5.1788    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5530   -5.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1214   -3.7200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193   -3.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9733   -4.2758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6522   -3.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2216   -2.3377    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6624   -1.6403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3973   -2.3047    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0434   -3.0021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0757   -2.2058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5165   -2.9032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3408   -2.8702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7815   -3.5676    0.0000 C   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
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  6  0  0  0
 12 17  1  0  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  1  0  0  0
 23 22  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  1  0  0  0  0
 27 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 25 39  1  0  0  0  0
 21 39  1  0  0  0  0
 39 40  1  6  0  0  0
 23 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  1  0  0  0
 43 44  1  1  0  0  0
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 45 46  1  6  0  0  0
 42 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  1  0  0  0
 10 52  1  1  0  0  0
 51 53  1  0  0  0  0
  8 53  1  0  0  0  0
 53 54  1  6  0  0  0
  6 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 55 58  1  0  0  0  0
  3 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
M  END

     RDKit          3D

132138  0  0  0  0  0  0  0  0999 V2000
   10.6571   -1.5272    1.9385 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9826   -0.6518    1.1246 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6194   -0.6448    1.3839 C   0  0  1  0  0  0  0  0  0  0  0  0
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    6.7538    0.6746    1.7722 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2751    0.8265    0.5083 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9283    0.5648    0.3655 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1388    1.6207   -0.0205 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5210    1.4735   -1.3698 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4077    0.4315   -1.2507 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0214   -0.8867   -1.5310 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1875   -2.1002   -1.2964 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9218   -2.3801    0.1418 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1136   -3.6257    0.5080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5803   -3.6138    0.7087 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0594   -3.5891    2.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0879   -2.0845   -2.1402 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309082217342D          

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M  END
> <DATABASE_ID>
NP0269936

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1COC(O[C@H]2C[C@H]3C[C@H](OC(=O)C[C@@H]4O[C@@H](C[C@H](OC5OCC(OC)C(OC)C5OC)[C@H]4C)C[C@H](OC(=O)C[C@H](O3)[C@@H]2C)[C@H]2C[C@@H]2C)[C@H]2C[C@@H]2C)C(OC)C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C44H72O16/c1-21-11-27(21)33-15-25-13-29(59-43-41(51-9)39(49-7)35(47-5)19-53-43)23(3)32(55-25)18-38(46)58-34(28-12-22(28)2)16-26-14-30(24(4)31(56-26)17-37(45)57-33)60-44-42(52-10)40(50-8)36(48-6)20-54-44/h21-36,39-44H,11-20H2,1-10H3/t21-,22-,23+,24+,25-,26-,27-,28-,29-,30-,31-,32-,33-,34-,35?,36?,39?,40?,41?,42?,43?,44?/m0/s1

> <INCHI_KEY>
CTMDQMUAHLSXCW-UHKIEBKESA-N

> <FORMULA>
C44H72O16

> <MOLECULAR_WEIGHT>
857.044

> <EXACT_MASS>
856.482036238

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
132

> <JCHEM_AVERAGE_POLARIZABILITY>
96.09342736385743

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,5S,7S,9S,10S,11S,15S,17S,19S,20S)-10,20-dimethyl-5,15-bis[(1S,2S)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1^{7,11}]docosane-3,13-dione

> <JCHEM_LOGP>
3.414067740666663

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.264344070295088

> <JCHEM_POLAR_SURFACE_AREA>
163.35999999999999

> <JCHEM_REFRACTIVITY>
211.61659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5S,7S,9S,10S,11S,15S,17S,19S,20S)-10,20-dimethyl-5,15-bis[(1S,2S)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1^{7,11}]docosane-3,13-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.343  -8.023   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.804  -8.084   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.981  -6.783   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.443  -6.844   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.620  -5.542   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.336  -4.179   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.513  -2.877   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.026  -2.939   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.848  -1.637   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.387  -1.699   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.307  -0.100   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.621   0.704   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.089   2.149   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.906   3.134   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.351   3.666   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.336   4.850   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.142   0.943   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.639   0.583   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.285   1.981   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.885  -0.323   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.688  -1.637   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.866  -2.939   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.582  -4.302   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.120  -4.364   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.943  -3.062   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      13.482  -3.123   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.198  -4.487   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      15.737  -4.548   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      16.453  -5.912   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.630  -7.214   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      16.346  -8.577   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      17.885  -8.639   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      14.091  -7.152   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      13.269  -8.454   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      11.730  -8.392   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      13.375  -5.789   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      11.836  -5.727   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      11.014  -7.029   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.227  -1.699   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.050  -0.397   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       8.661  -5.901   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       7.348  -6.704   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       7.880  -8.149   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       9.063  -9.135   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       7.618  -9.667   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       6.632 -10.850   0.000  0.00  0.00           C+0
HETATM   47  O   UNK     0       5.827  -6.944   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0       4.329  -6.583   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       3.684  -7.982   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       3.084  -5.677   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       2.280  -4.364   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       3.103  -3.062   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       0.742  -4.302   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -0.081  -5.604   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -3.875  -4.117   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -4.591  -2.754   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      -6.129  -2.692   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -4.697  -5.419   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      -6.236  -5.358   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      -7.059  -6.660   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   58                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   55                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   53                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   52                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13   15                                                       
CONECT   15   14   13   16                                                  
CONECT   16   15                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   39                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   41                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   39                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   36                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   27   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   25   21   40                                                  
CONECT   40   39                                                            
CONECT   41   23   42                                                       
CONECT   42   41   43   47                                                  
CONECT   43   42   44   45                                                  
CONECT   44   43   45                                                       
CONECT   45   44   43   46                                                  
CONECT   46   45                                                            
CONECT   47   42   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51                                                       
CONECT   51   50   52   53                                                  
CONECT   52   51   10                                                       
CONECT   53   51    8   54                                                  
CONECT   54   53                                                            
CONECT   55    6   56   58                                                  
CONECT   56   55   57                                                       
CONECT   57   56                                                            
CONECT   58   55    3   59                                                  
CONECT   59   58   60                                                       
CONECT   60   59                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  132    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₄H₇₂O₁₆

Average Mass

857.0440 Da

Monoisotopic Mass

856.48204 Da

IUPAC Name

(1S,5S,7S,9S,10S,11S,15S,17S,19S,20S)-10,20-dimethyl-5,15-bis[(1S,2S)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1^{7,11}]docosane-3,13-dione

Traditional Name

(1S,5S,7S,9S,10S,11S,15S,17S,19S,20S)-10,20-dimethyl-5,15-bis[(1S,2S)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1^{7,11}]docosane-3,13-dione

CAS Registry Number

Not Available

SMILES

COC1COC(O[C@H]2C[C@H]3C[C@H](OC(=O)C[C@@H]4O[C@@H](C[C@H](OC5OCC(OC)C(OC)C5OC)[C@H]4C)C[C@H](OC(=O)C[C@H](O3)[C@@H]2C)[C@H]2C[C@@H]2C)[C@H]2C[C@@H]2C)C(OC)C1OC

InChI Identifier

InChI=1S/C44H72O16/c1-21-11-27(21)33-15-25-13-29(59-43-41(51-9)39(49-7)35(47-5)19-53-43)23(3)32(55-25)18-38(46)58-34(28-12-22(28)2)16-26-14-30(24(4)31(56-26)17-37(45)57-33)60-44-42(52-10)40(50-8)36(48-6)20-54-44/h21-36,39-44H,11-20H2,1-10H3/t21-,22-,23+,24+,25-,26-,27-,28-,29-,30-,31-,32-,33-,34-,35?,36?,39?,40?,41?,42?,43?,44?/m0/s1

InChI Key

CTMDQMUAHLSXCW-UHKIEBKESA-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
Stelletta clavosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Glycosyl compound
O-glycosyl compound
Dicarboxylic acid or derivatives
Oxane
Monosaccharide
Carboxylic acid ester
Lactone
Acetal
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.41	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	163.36 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	211.62 m³·mol⁻¹	ChemAxon
Polarizability	96.09 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

C00045263

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

45027815

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cabrera JM, Krische MJ: Total Synthesis of Clavosolide A via Asymmetric Alcohol-Mediated Carbonyl Allylation: Beyond Protecting Groups or Chiral Auxiliaries in Polyketide Construction. Angew Chem Int Ed Engl. 2019 Jul 29;58(31):10718-10722. doi: 10.1002/anie.201906259. Epub 2019 Jun 24. [PubMed:31166641 ]
Koschker P, Breit B: Branching Out: Rhodium-Catalyzed Allylation with Alkynes and Allenes. Acc Chem Res. 2016 Aug 16;49(8):1524-36. doi: 10.1021/acs.accounts.6b00252. Epub 2016 Jul 25. [PubMed:27455048 ]
Millan A, Smith JR, Chen JL, Aggarwal VK: Tandem Allylboration-Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (-)-Clavosolide A. Angew Chem Int Ed Engl. 2016 Feb 12;55(7):2498-502. doi: 10.1002/anie.201511140. Epub 2016 Jan 14. [PubMed:26766494 ]
Haydl AM, Breit B: Atom-Economical Dimerization Strategy by the Rhodium-Catalyzed Addition of Carboxylic Acids to Allenes: Protecting-Group-Free Synthesis of Clavosolide A and Late-Stage Modification. Angew Chem Int Ed Engl. 2015 Dec 14;54(51):15530-4. doi: 10.1002/anie.201506618. Epub 2015 Nov 10. [PubMed:26553131 ]
Baker JB, Kim H, Hong J: Total Synthesis of Clavosolide A via Tandem Allylic Oxidation/Oxa-Conjugate Addition Reaction. Tetrahedron Lett. 2015 Jun 3;56(23):3120-3122. doi: 10.1016/j.tetlet.2014.11.135. [PubMed:26236051 ]
LOTUS database [Link]

Showing NP-Card for (1s,5s,7s,9s,10s,11s,15s,17s,19s,20s)-10,20-dimethyl-5,15-bis[(1s,2s)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1⁷,¹¹]docosane-3,13-dione (NP0269936)

MOL for NP0269936 ((1s,5s,7s,9s,10s,11s,15s,17s,19s,20s)-10,20-dimethyl-5,15-bis[(1s,2s)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1⁷,¹¹]docosane-3,13-dione)

3D MOL for NP0269936 ((1s,5s,7s,9s,10s,11s,15s,17s,19s,20s)-10,20-dimethyl-5,15-bis[(1s,2s)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1⁷,¹¹]docosane-3,13-dione)

3D SDF for NP0269936 ((1s,5s,7s,9s,10s,11s,15s,17s,19s,20s)-10,20-dimethyl-5,15-bis[(1s,2s)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1⁷,¹¹]docosane-3,13-dione)

3D-SDF for NP0269936 ((1s,5s,7s,9s,10s,11s,15s,17s,19s,20s)-10,20-dimethyl-5,15-bis[(1s,2s)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1⁷,¹¹]docosane-3,13-dione)

PDB for NP0269936 ((1s,5s,7s,9s,10s,11s,15s,17s,19s,20s)-10,20-dimethyl-5,15-bis[(1s,2s)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1⁷,¹¹]docosane-3,13-dione)

3D PDB for NP0269936 ((1s,5s,7s,9s,10s,11s,15s,17s,19s,20s)-10,20-dimethyl-5,15-bis[(1s,2s)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1⁷,¹¹]docosane-3,13-dione)

SMILES for NP0269936 ((1s,5s,7s,9s,10s,11s,15s,17s,19s,20s)-10,20-dimethyl-5,15-bis[(1s,2s)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1⁷,¹¹]docosane-3,13-dione)

INCHI for NP0269936 ((1s,5s,7s,9s,10s,11s,15s,17s,19s,20s)-10,20-dimethyl-5,15-bis[(1s,2s)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1⁷,¹¹]docosane-3,13-dione)

Structure for NP0269936 ((1s,5s,7s,9s,10s,11s,15s,17s,19s,20s)-10,20-dimethyl-5,15-bis[(1s,2s)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1⁷,¹¹]docosane-3,13-dione)

3D Structure for NP0269936 ((1s,5s,7s,9s,10s,11s,15s,17s,19s,20s)-10,20-dimethyl-5,15-bis[(1s,2s)-2-methylcyclopropyl]-9,19-bis[(3,4,5-trimethoxyoxan-2-yl)oxy]-4,14,21,22-tetraoxatricyclo[15.3.1.1⁷,¹¹]docosane-3,13-dione)