NP-MRD: Showing NP-Card for makilactone F (NP0038306)

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Record Information

Version

2.0

Created at

2021-06-20 21:02:02 UTC

Updated at

2021-06-30 00:11:01 UTC

NP-MRD ID

NP0038306

Secondary Accession Numbers

None

Natural Product Identification

Common Name

makilactone F

Provided By

JEOL Database JEOL Logo

Description

Makilactone F 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 F is found in Podocarpus macrophyllus and Podocarpus macrophyllus D. DON. makilactone F was first documented in 2009 (Sato, K., et al.). Based on a literature review very few articles have been published on Makilactone F.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123023D          

 49 53  0  0  0  0            999 V2000
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   -3.3992   -0.7374   -4.3955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0160   -2.1150   -4.3038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4180    0.1330   -3.5805 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6521    1.5331   -3.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1047    2.5271   -3.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1715    3.7027   -3.4930 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306202123023D          

 49 53  0  0  0  0            999 V2000
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 18 27  1  0  0  0  0
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 10 12  1  0  0  0  0
 23 22  1  0  0  0  0
 20 22  1  0  0  0  0
 10 27  1  0  0  0  0
 20 21  2  0  0  0  0
 10  9  1  0  0  0  0
 14 15  1  0  0  0  0
 27 23  1  0  0  0  0
 12 13  1  0  0  0  0
 23 24  1  0  0  0  0
 18 19  1  1  0  0  0
 24 26  1  0  0  0  0
  6  7  2  0  0  0  0
  9 26  1  0  0  0  0
  4  2  1  0  0  0  0
  9  8  2  0  0  0  0
  4 33  1  6  0  0  0
 26  4  1  0  0  0  0
  2  3  1  0  0  0  0
  5  6  1  0  0  0  0
  2  1  1  0  0  0  0
  6  8  1  0  0  0  0
 26 25  1  1  0  0  0
 24 25  1  0  0  0  0
 10 11  1  6  0  0  0
 27 49  1  1  0  0  0
 14 40  1  6  0  0  0
 16 42  1  1  0  0  0
 12 38  1  1  0  0  0
 23 47  1  1  0  0  0
 24 48  1  6  0  0  0
  8 34  1  0  0  0  0
 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
 11 37  1  0  0  0  0
 17 43  1  0  0  0  0
 15 41  1  0  0  0  0
 13 39  1  0  0  0  0
 19 44  1  0  0  0  0
 19 45  1  0  0  0  0
 19 46  1  0  0  0  0
  2 31  1  1  0  0  0
  3 32  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038306

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[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])(O[H])[C@]3([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O9/c1-5(19)13-18-6(4-7(20)25-13)16(2)10-9(14(18)27-18)26-15(24)17(10,3)12(23)8(21)11(16)22/h4-5,8-14,19,21-23H,1-3H3/t5-,8-,9+,10-,11-,12+,13-,14-,16-,17-,18-/m1/s1

> <INCHI_KEY>
XPNMRKYBBVWJQO-YHLPLSSQSA-N

> <FORMULA>
C18H22O9

> <MOLECULAR_WEIGHT>
382.365

> <EXACT_MASS>
382.126382288

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
36.376210140100255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4S,5R,10S,11S,12R,13R,14R,17R)-11,12,13-trihydroxy-5-[(1R)-1-hydroxyethyl]-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>
-0.52

> <JCHEM_LOGP>
-1.6723102259999996

> <ALOGPS_LOGS>
-1.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.837695461002934

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.8718588463901

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0732101461780488

> <JCHEM_POLAR_SURFACE_AREA>
146.05

> <JCHEM_REFRACTIVITY>
85.27539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.73e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,5R,10S,11S,12R,13R,14R,17R)-11,12,13-trihydroxy-5-[(1R)-1-hydroxyethyl]-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

 49 53  0  0  0  0  0  0  0  0999 V2000
   -3.4137   -0.3564   -5.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3992   -0.7374   -4.3955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0160   -2.1150   -4.3038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4180    0.1330   -3.5805 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6521    1.5331   -3.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1047    2.5271   -3.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1715    3.7027   -3.4930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4043    2.1485   -1.9121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5734    0.9232   -1.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8335    0.3539   -0.1620 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1731   -0.6803   -0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0162    1.3683    0.6902 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0487    1.9579   -0.0658 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6146    0.6756    1.9108 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3280    1.6738    2.6652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405    0.0299    2.8059 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2198   -0.6746    3.8647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5065   -0.8206    2.1033 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6619   -1.0594    3.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780   -2.1824    1.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2237   -2.8806    2.1307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7767   -2.5112    0.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6631   -1.4268    0.1448 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9068   -1.2764   -1.3219 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8395   -0.2170   -1.5968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984   -0.0130   -2.0731 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9747   -0.2238    0.7726 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4128   -0.4504   -6.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7707    0.6661   -6.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0659   -1.0326   -6.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4189   -0.6404   -4.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6513   -2.6280   -4.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3965   -0.1130   -3.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7599    2.9099   -1.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7385   -1.2226   -0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9091   -0.1794   -1.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3007   -1.4380   -1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6558    2.1964    1.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6175    2.4047    0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3829   -0.0473    1.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427    1.2512    3.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9574    0.8573    3.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4815   -1.5621    3.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2827   -1.4533    4.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1929   -0.1248    3.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3969   -1.7896    2.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6295   -1.6443    0.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0452   -2.2158   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7043    0.5784    0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 16  1  0
  5  4  1  0
 14 12  1  0
 16 18  1  0
 16 17  1  0
 18 27  1  0
 18 20  1  0
 10 12  1  0
 23 22  1  0
 20 22  1  0
 10 27  1  0
 20 21  2  0
 10  9  1  0
 14 15  1  0
 27 23  1  0
 12 13  1  0
 23 24  1  0
 18 19  1  1
 24 26  1  0
  6  7  2  0
  9 26  1  0
  4  2  1  0
  9  8  2  0
  4 33  1  6
 26  4  1  0
  2  3  1  0
  5  6  1  0
  2  1  1  0
  6  8  1  0
 26 25  1  1
 24 25  1  0
 10 11  1  6
 27 49  1  1
 14 40  1  6
 16 42  1  1
 12 38  1  1
 23 47  1  1
 24 48  1  6
  8 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 17 43  1  0
 15 41  1  0
 13 39  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
  2 31  1  1
  3 32  1  0
  1 28  1  0
  1 29  1  0
  1 30  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      -3.414  -0.356  -5.876  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.399  -0.737  -4.396  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.016  -2.115  -4.304  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.418   0.133  -3.580  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.652   1.533  -3.903  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.105   2.527  -3.156  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.172   3.703  -3.493  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.404   2.148  -1.912  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.573   0.923  -1.387  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.834   0.354  -0.162  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.173  -0.680  -0.764  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.016   1.368   0.690  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.049   1.958  -0.066  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.615   0.676   1.911  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.328   1.674   2.665  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.441   0.030   2.806  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.220  -0.675   3.865  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.506  -0.821   2.103  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.662  -1.059   3.104  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.078  -2.182   1.609  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.224  -2.881   2.131  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.777  -2.511   0.468  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.663  -1.427   0.145  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.907  -1.276  -1.322  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.840  -0.217  -1.597  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.498  -0.013  -2.073  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.975  -0.224   0.773  0.00  0.00           C+0
HETATM   28  H   UNK     0      -2.413  -0.450  -6.311  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.771   0.666  -6.029  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.066  -1.033  -6.439  0.00  0.00           H+0
HETATM   31  H   UNK     0      -4.419  -0.640  -4.007  0.00  0.00           H+0
HETATM   32  H   UNK     0      -3.651  -2.628  -4.835  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.397  -0.113  -3.903  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.760   2.910  -1.493  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.739  -1.223  -0.004  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.909  -0.179  -1.406  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.301  -1.438  -1.395  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.656   2.196   1.022  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.617   2.405   0.596  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.383  -0.047   1.621  0.00  0.00           H+0
HETATM   41  H   UNK     0       1.543   1.251   3.523  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.957   0.857   3.312  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.482  -1.562   3.538  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.283  -1.453   4.055  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.193  -0.125   3.316  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.397  -1.790   2.751  0.00  0.00           H+0
HETATM   47  H   UNK     0      -3.630  -1.644   0.614  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.045  -2.216  -1.836  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.704   0.578   0.956  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    4    3    1   31                                             
CONECT    3    2   32                                                       
CONECT    4    5    2   33   26                                             
CONECT    5    4    6                                                       
CONECT    6    7    5    8                                                  
CONECT    7    6                                                            
CONECT    8    9    6   34                                                  
CONECT    9   10   26    8                                                  
CONECT   10   12   27    9   11                                             
CONECT   11   10   35   36   37                                             
CONECT   12   14   10   13   38                                             
CONECT   13   12   39                                                       
CONECT   14   16   12   15   40                                             
CONECT   15   14   41                                                       
CONECT   16   14   18   17   42                                             
CONECT   17   16   43                                                       
CONECT   18   16   27   20   19                                             
CONECT   19   18   44   45   46                                             
CONECT   20   18   22   21                                                  
CONECT   21   20                                                            
CONECT   22   23   20                                                       
CONECT   23   22   27   24   47                                             
CONECT   24   23   26   25   48                                             
CONECT   25   26   24                                                       
CONECT   26   24    9    4   25                                             
CONECT   27   18   10   23   49                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    2                                                            
CONECT   32    3                                                            
CONECT   33    4                                                            
CONECT   34    8                                                            
CONECT   35   11                                                            
CONECT   36   11                                                            
CONECT   37   11                                                            
CONECT   38   12                                                            
CONECT   39   13                                                            
CONECT   40   14                                                            
CONECT   41   15                                                            
CONECT   42   16                                                            
CONECT   43   17                                                            
CONECT   44   19                                                            
CONECT   45   19                                                            
CONECT   46   19                                                            
CONECT   47   23                                                            
CONECT   48   24                                                            
CONECT   49   27                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  106    0
END

RDKit          3D

49 53  0  0  0  0  0  0  0  0999 V2000
   -3.4137   -0.3564   -5.8756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3992   -0.7374   -4.3955 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0160   -2.1150   -4.3038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4180    0.1330   -3.5805 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6521    1.5331   -3.9033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1047    2.5271   -3.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1715    3.7027   -3.4930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4043    2.1485   -1.9121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5734    0.9232   -1.3870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8335    0.3539   -0.1620 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1731   -0.6803   -0.7639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0162    1.3683    0.6902 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0487    1.9579   -0.0658 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6146    0.6756    1.9108 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3280    1.6738    2.6652 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4405    0.0299    2.8059 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2198   -0.6746    3.8647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5065   -0.8206    2.1033 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6619   -1.0594    3.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0780   -2.1824    1.6094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2237   -2.8806    2.1307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7767   -2.5112    0.4684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6631   -1.4268    0.1448 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9068   -1.2764   -1.3219 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8395   -0.2170   -1.5968 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984   -0.0130   -2.0731 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9747   -0.2238    0.7726 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4128   -0.4504   -6.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7707    0.6661   -6.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0659   -1.0326   -6.4393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4189   -0.6404   -4.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6513   -2.6280   -4.8350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3965   -0.1130   -3.9032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7599    2.9099   -1.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7385   -1.2226   -0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9091   -0.1794   -1.4056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3007   -1.4380   -1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6558    2.1964    1.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6175    2.4047    0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3829   -0.0473    1.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5427    1.2512    3.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9574    0.8573    3.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4815   -1.5621    3.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2827   -1.4533    4.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1929   -0.1248    3.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3969   -1.7896    2.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6295   -1.6443    0.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0452   -2.2158   -1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7043    0.5784    0.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 16  1  0
  5  4  1  0
 14 12  1  0
 16 18  1  0
 16 17  1  0
 18 27  1  0
 18 20  1  0
 10 12  1  0
 23 22  1  0
 20 22  1  0
 10 27  1  0
 20 21  2  0
 10  9  1  0
 14 15  1  0
 27 23  1  0
 12 13  1  0
 23 24  1  0
 18 19  1  1
 24 26  1  0
  6  7  2  0
  9 26  1  0
  4  2  1  0
  9  8  2  0
  4 33  1  6
 26  4  1  0
  2  3  1  0
  5  6  1  0
  2  1  1  0
  6  8  1  0
 26 25  1  1
 24 25  1  0
 10 11  1  6
 27 49  1  1
 14 40  1  6
 16 42  1  1
 12 38  1  1
 23 47  1  1
 24 48  1  6
  8 34  1  0
 11 35  1  0
 11 36  1  0
 11 37  1  0
 17 43  1  0
 15 41  1  0
 13 39  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
  2 31  1  1
  3 32  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₂O₉

Average Mass

382.3650 Da

Monoisotopic Mass

382.12638 Da

IUPAC Name

(1S,2R,4S,5R,10S,11S,12R,13R,14R,17R)-11,12,13-trihydroxy-5-[(1R)-1-hydroxyethyl]-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,4S,5R,10S,11S,12R,13R,14R,17R)-11,12,13-trihydroxy-5-[(1R)-1-hydroxyethyl]-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]O[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])(O[H])[C@]3([H])O[H]

InChI Identifier

InChI=1S/C18H22O9/c1-5(19)13-18-6(4-7(20)25-13)16(2)10-9(14(18)27-18)26-15(24)17(10,3)12(23)8(21)11(16)22/h4-5,8-14,19,21-23H,1-3H3/t5-,8-,9+,10-,11-,12+,13-,14-,16-,17-,18-/m1/s1

InChI Key

XPNMRKYBBVWJQO-YHLPLSSQSA-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

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	-0.52	ALOGPS
logP	-1.7	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	12.87	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	146.05 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.28 m³·mol⁻¹	ChemAxon
Polarizability	36.38 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

44179070

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 F (NP0038306)

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