NP-MRD: Showing NP-Card for makilactone J (NP0038310)

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Record Information

Version

2.0

Created at

2021-06-20 21:02:11 UTC

Updated at

2021-06-30 00:11:02 UTC

NP-MRD ID

NP0038310

Secondary Accession Numbers

None

Natural Product Identification

Common Name

makilactone J

Provided By

JEOL Database JEOL Logo

Description

Makilactone J belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. makilactone J is found in Podocarpus macrophyllus and Podocarpus macrophyllus D. DON. makilactone J was first documented in 2009 (Sato, K., et al.). Based on a literature review very few articles have been published on Makilactone J.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123023D          

 51 55  0  0  0  0            999 V2000
   -3.8832    0.3385   -0.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9511   -0.0834    0.2859 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5495    0.4016    1.6144 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7547   -0.3147    1.8748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5291    0.4600    0.0238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5024    1.8744    0.3659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353    2.5489    0.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202123023D          

 51 55  0  0  0  0            999 V2000
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    2.5707   -3.8461    3.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2929   -3.9249    2.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7603   -2.9063    2.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1424   -0.9062    2.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0936   -2.4097    0.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0  0  0  0
  6  5  1  0  0  0  0
 15 13  1  0  0  0  0
 16 18  1  0  0  0  0
 18 20  1  0  0  0  0
 18 24  1  0  0  0  0
 23 22  1  0  0  0  0
 20 22  1  0  0  0  0
 11 13  1  0  0  0  0
 20 21  2  0  0  0  0
 11 24  1  0  0  0  0
 13 14  1  0  0  0  0
 11 10  1  0  0  0  0
 18 19  1  1  0  0  0
 24 23  1  0  0  0  0
  7  8  2  0  0  0  0
 23 25  1  0  0  0  0
  5  2  1  0  0  0  0
 25 27  1  0  0  0  0
  5 35  1  6  0  0  0
 10 27  1  0  0  0  0
  2  1  1  0  0  0  0
 10  9  2  0  0  0  0
  2  3  1  0  0  0  0
 27  5  1  0  0  0  0
 27 26  1  1  0  0  0
 25 26  1  0  0  0  0
  6  7  1  0  0  0  0
 24 50  1  1  0  0  0
  7  9  1  0  0  0  0
  3  4  1  0  0  0  0
 11 12  1  6  0  0  0
 16 17  1  0  0  0  0
 15 42  1  0  0  0  0
 15 43  1  0  0  0  0
 16 44  1  1  0  0  0
 13 40  1  1  0  0  0
 23 49  1  1  0  0  0
 25 51  1  6  0  0  0
  9 36  1  0  0  0  0
 12 37  1  0  0  0  0
 12 38  1  0  0  0  0
 12 39  1  0  0  0  0
 14 41  1  0  0  0  0
 19 46  1  0  0  0  0
 19 47  1  0  0  0  0
 19 48  1  0  0  0  0
  2 31  1  1  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  3 32  1  0  0  0  0
  3 33  1  0  0  0  0
  4 34  1  0  0  0  0
 17 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038310

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]([H])(C([H])([H])[H])[C@@]1([H])OC(=O)C([H])=C2[C@@]11O[C@]1([H])[C@@]1([H])OC(=O)[C@]3(C([H])([H])[H])[C@@]1([H])[C@]2(C([H])([H])[H])[C@]([H])(O[H])C([H])([H])[C@]3([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O8/c1-7(6-20)14-19-8(4-11(23)25-14)17(2)9(21)5-10(22)18(3)13(17)12(15(19)27-19)26-16(18)24/h4,7,9-10,12-15,20-22H,5-6H2,1-3H3/t7-,9-,10+,12+,13-,14-,15-,17+,18+,19-/m1/s1

> <INCHI_KEY>
FVLDMYYKZPDQOL-NDSMYCMQSA-N

> <FORMULA>
C19H24O8

> <MOLECULAR_WEIGHT>
380.393

> <EXACT_MASS>
380.147117733

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.45671246081308

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4R,5R,10S,11R,13S,14R,17R)-11,13-dihydroxy-5-[(2R)-1-hydroxypropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0^{2,4}.0^{4,9}.0^{14,17}]heptadec-8-ene-7,15-dione

> <ALOGPS_LOGP>
-0.09

> <JCHEM_LOGP>
-0.8593072713333337

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.775228418265158

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.11921695595532

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6275902172624983

> <JCHEM_POLAR_SURFACE_AREA>
125.82000000000001

> <JCHEM_REFRACTIVITY>
89.04129999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4R,5R,10S,11R,13S,14R,17R)-11,13-dihydroxy-5-[(2R)-1-hydroxypropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0^{2,4}.0^{4,9}.0^{14,17}]heptadec-8-ene-7,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 55  0  0  0  0  0  0  0  0999 V2000
   -3.8832    0.3385   -0.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9511   -0.0834    0.2859 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5495    0.4016    1.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7547   -0.3147    1.8748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5291    0.4600    0.0238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5024    1.8744    0.3659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353    2.5489    0.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3057    3.7544    0.7414 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219    1.7851    0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9129    0.4433    0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1274   -0.4764    0.2338 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8645   -1.0841   -1.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287    0.2126    0.2011 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6156    1.1483   -0.8737 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6439   -0.8200    0.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6416   -1.8796    1.0989 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6260   -2.8653    0.8013 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2852   -2.5035    1.4567 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4402   -3.2359    2.8117 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7129   -3.5153    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3633   -4.2758   -0.2103 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3354   -3.4422    0.4918 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9353   -2.4207    1.4178 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1375   -1.4903    1.4488 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3351   -1.7366    1.0291 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7254   -0.7662    2.0139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3820   -0.2399    0.7265 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5066   -0.0323   -1.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9668    1.4285   -0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8897   -0.0709   -0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9428   -1.1793    0.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8787    0.2286    2.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7902    1.4697    1.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1248    0.0489    2.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342    0.3950   -1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072    2.3833    0.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8600   -0.2989   -1.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6206   -1.8114   -1.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8965   -1.5867   -1.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6931    0.7675    1.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149    1.5232   -0.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6066   -1.2806   -0.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -0.3087    0.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0095   -1.3707    2.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2645   -3.4805    0.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6070   -2.5206    3.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5707   -3.8461    3.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2929   -3.9249    2.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7603   -2.9063    2.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1424   -0.9062    2.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0936   -2.4097    0.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
  6  5  1  0
 15 13  1  0
 16 18  1  0
 18 20  1  0
 18 24  1  0
 23 22  1  0
 20 22  1  0
 11 13  1  0
 20 21  2  0
 11 24  1  0
 13 14  1  0
 11 10  1  0
 18 19  1  1
 24 23  1  0
  7  8  2  0
 23 25  1  0
  5  2  1  0
 25 27  1  0
  5 35  1  6
 10 27  1  0
  2  1  1  0
 10  9  2  0
  2  3  1  0
 27  5  1  0
 27 26  1  1
 25 26  1  0
  6  7  1  0
 24 50  1  1
  7  9  1  0
  3  4  1  0
 11 12  1  6
 16 17  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  1
 13 40  1  1
 23 49  1  1
 25 51  1  6
  9 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 14 41  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
  2 31  1  1
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
 17 45  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.883   0.339  -0.865  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.951  -0.083   0.286  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.550   0.402   1.614  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.755  -0.315   1.875  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.529   0.460   0.024  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.502   1.874   0.366  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.335   2.549   0.528  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.306   3.754   0.741  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.922   1.785   0.413  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.913   0.443   0.482  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.127  -0.476   0.234  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.865  -1.084  -1.183  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.529   0.213   0.201  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.616   1.148  -0.874  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.644  -0.820   0.010  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.642  -1.880   1.099  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.626  -2.865   0.801  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.285  -2.503   1.457  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.440  -3.236   2.812  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.713  -3.515   0.488  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.363  -4.276  -0.210  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.335  -3.442   0.492  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.935  -2.421   1.418  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.138  -1.490   1.449  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.335  -1.737   1.029  0.00  0.00           C+0
HETATM   26  O   UNK     0      -0.725  -0.766   2.014  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.382  -0.240   0.727  0.00  0.00           C+0
HETATM   28  H   UNK     0      -3.507  -0.032  -1.824  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.967   1.429  -0.932  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.890  -0.071  -0.730  0.00  0.00           H+0
HETATM   31  H   UNK     0      -2.943  -1.179   0.276  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.879   0.229   2.458  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.790   1.470   1.579  0.00  0.00           H+0
HETATM   34  H   UNK     0      -5.125   0.049   2.698  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.334   0.395  -1.056  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.807   2.383   0.244  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.860  -0.299  -1.950  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.621  -1.811  -1.485  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.897  -1.587  -1.272  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.693   0.768   1.133  0.00  0.00           H+0
HETATM   41  H   UNK     0       4.515   1.523  -0.880  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.607  -1.281  -0.984  0.00  0.00           H+0
HETATM   43  H   UNK     0       5.617  -0.309   0.008  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.010  -1.371   2.001  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.264  -3.481   0.129  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.607  -2.521   3.624  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.571  -3.846   3.076  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.293  -3.925   2.790  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.760  -2.906   2.385  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.142  -0.906   2.381  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.094  -2.410   0.657  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    5    1    3   31                                             
CONECT    3    2    4   32   33                                             
CONECT    4    3   34                                                       
CONECT    5    6    2   35   27                                             
CONECT    6    5    7                                                       
CONECT    7    8    6    9                                                  
CONECT    8    7                                                            
CONECT    9   10    7   36                                                  
CONECT   10   11   27    9                                                  
CONECT   11   13   24   10   12                                             
CONECT   12   11   37   38   39                                             
CONECT   13   15   11   14   40                                             
CONECT   14   13   41                                                       
CONECT   15   16   13   42   43                                             
CONECT   16   15   18   17   44                                             
CONECT   17   16   45                                                       
CONECT   18   16   20   24   19                                             
CONECT   19   18   46   47   48                                             
CONECT   20   18   22   21                                                  
CONECT   21   20                                                            
CONECT   22   23   20                                                       
CONECT   23   22   24   25   49                                             
CONECT   24   18   11   23   50                                             
CONECT   25   23   27   26   51                                             
CONECT   26   27   25                                                       
CONECT   27   25   10    5   26                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    2                                                            
CONECT   32    3                                                            
CONECT   33    3                                                            
CONECT   34    4                                                            
CONECT   35    5                                                            
CONECT   36    9                                                            
CONECT   37   12                                                            
CONECT   38   12                                                            
CONECT   39   12                                                            
CONECT   40   13                                                            
CONECT   41   14                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   17                                                            
CONECT   46   19                                                            
CONECT   47   19                                                            
CONECT   48   19                                                            
CONECT   49   23                                                            
CONECT   50   24                                                            
CONECT   51   25                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  110    0
END

RDKit          3D

51 55  0  0  0  0  0  0  0  0999 V2000
   -3.8832    0.3385   -0.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9511   -0.0834    0.2859 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5495    0.4016    1.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7547   -0.3147    1.8748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5291    0.4600    0.0238 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5024    1.8744    0.3659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3353    2.5489    0.5280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3057    3.7544    0.7414 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9219    1.7851    0.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9129    0.4433    0.4815 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1274   -0.4764    0.2338 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8645   -1.0841   -1.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287    0.2126    0.2011 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6156    1.1483   -0.8737 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6439   -0.8200    0.0100 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6416   -1.8796    1.0989 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6260   -2.8653    0.8013 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2852   -2.5035    1.4567 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4402   -3.2359    2.8117 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7129   -3.5153    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3633   -4.2758   -0.2103 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3354   -3.4422    0.4918 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9353   -2.4207    1.4178 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1375   -1.4903    1.4488 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3351   -1.7366    1.0291 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7254   -0.7662    2.0139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3820   -0.2399    0.7265 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5066   -0.0323   -1.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9668    1.4285   -0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8897   -0.0709   -0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9428   -1.1793    0.2763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8787    0.2286    2.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7902    1.4697    1.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1248    0.0489    2.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342    0.3950   -1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8072    2.3833    0.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8600   -0.2989   -1.9501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6206   -1.8114   -1.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8965   -1.5867   -1.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6931    0.7675    1.1334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149    1.5232   -0.8801 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6066   -1.2806   -0.9841 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -0.3087    0.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0095   -1.3707    2.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2645   -3.4805    0.1293 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6070   -2.5206    3.6245 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5707   -3.8461    3.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2929   -3.9249    2.7902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7603   -2.9063    2.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1424   -0.9062    2.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0936   -2.4097    0.6573 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
  6  5  1  0
 15 13  1  0
 16 18  1  0
 18 20  1  0
 18 24  1  0
 23 22  1  0
 20 22  1  0
 11 13  1  0
 20 21  2  0
 11 24  1  0
 13 14  1  0
 11 10  1  0
 18 19  1  1
 24 23  1  0
  7  8  2  0
 23 25  1  0
  5  2  1  0
 25 27  1  0
  5 35  1  6
 10 27  1  0
  2  1  1  0
 10  9  2  0
  2  3  1  0
 27  5  1  0
 27 26  1  1
 25 26  1  0
  6  7  1  0
 24 50  1  1
  7  9  1  0
  3  4  1  0
 11 12  1  6
 16 17  1  0
 15 42  1  0
 15 43  1  0
 16 44  1  1
 13 40  1  1
 23 49  1  1
 25 51  1  6
  9 36  1  0
 12 37  1  0
 12 38  1  0
 12 39  1  0
 14 41  1  0
 19 46  1  0
 19 47  1  0
 19 48  1  0
  2 31  1  1
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
 17 45  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₄O₈

Average Mass

380.3930 Da

Monoisotopic Mass

380.14712 Da

IUPAC Name

(1S,2R,4R,5R,10S,11R,13S,14R,17R)-11,13-dihydroxy-5-[(2R)-1-hydroxypropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0^{2,4}.0^{4,9}.0^{14,17}]heptadec-8-ene-7,15-dione

Traditional Name

(1S,2R,4R,5R,10S,11R,13S,14R,17R)-11,13-dihydroxy-5-[(2R)-1-hydroxypropan-2-yl]-10,14-dimethyl-3,6,16-trioxapentacyclo[8.6.1.0^{2,4}.0^{4,9}.0^{14,17}]heptadec-8-ene-7,15-dione

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])[C@@]([H])(C([H])([H])[H])[C@@]1([H])OC(=O)C([H])=C2[C@@]11O[C@]1([H])[C@@]1([H])OC(=O)[C@]3(C([H])([H])[H])[C@@]1([H])[C@]2(C([H])([H])[H])[C@]([H])(O[H])C([H])([H])[C@]3([H])O[H]

InChI Identifier

InChI=1S/C19H24O8/c1-7(6-20)14-19-8(4-11(23)25-14)17(2)9(21)5-10(22)18(3)13(17)12(15(19)27-19)26-16(18)24/h4,7,9-10,12-15,20-22H,5-6H2,1-3H3/t7-,9-,10+,12+,13-,14-,15-,17+,18+,19-/m1/s1

InChI Key

FVLDMYYKZPDQOL-NDSMYCMQSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, 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
Podocarpus macrophyllus	LOTUS Database	35616633
Podocarpus macrophyllus D. DON	JEOL database	Sato, K., et al, Chem. Pharm. Bull. 57, 668 (2009)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Oxepane
Dihydropyranone
Pyran
Gamma butyrolactone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-0.09	ALOGPS
logP	-0.86	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	14.12	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	125.82 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	89.04 m³·mol⁻¹	ChemAxon
Polarizability	37.46 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

44179141

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sato, K., et al. (2009). Sato, K., et al, Chem. Pharm. Bull. 57, 668 (2009). Chem. Pharm. Bull..

Showing NP-Card for makilactone J (NP0038310)

MOL for NP0038310 (makilactone J)

3D MOL for NP0038310 (makilactone J)

3D SDF for NP0038310 (makilactone J)

3D-SDF for NP0038310 (makilactone J)

PDB for NP0038310 (makilactone J)

3D PDB for NP0038310 (makilactone J)

SMILES for NP0038310 (makilactone J)

INCHI for NP0038310 (makilactone J)

Structure for NP0038310 (makilactone J)

3D Structure for NP0038310 (makilactone J)