NP-MRD: Showing NP-Card for Neosarcodonin C (NP0004060)

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Record Information

Version

2.0

Created at

2020-12-09 01:33:49 UTC

Updated at

2021-07-15 16:48:07 UTC

NP-MRD ID

NP0004060

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Neosarcodonin C

Provided By

NPAtlas

Description

(1R,2R,5R,10R,12R,13S,16S)-8-(1-hydroxypropan-2-yl)-12,16-dimethoxy-2,5-dimethyl-15-oxatetracyclo[11.2.1.0²,¹⁰.0⁵,⁹]Hexadec-8-en-14-ol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Neosarcodonin C is found in Sarcodon scabrosus. Neosarcodonin C was first documented in 2002 (PMID: 11866103). Based on a literature review very few articles have been published on (1R,2R,5R,10R,12R,13S,16S)-8-(1-hydroxypropan-2-yl)-12,16-dimethoxy-2,5-dimethyl-15-oxatetracyclo[11.2.1.0²,¹⁰.0⁵,⁹]Hexadec-8-en-14-ol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118033D          

 63 66  0  0  0  0            999 V2000
    4.1202   -0.8603    2.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9953   -0.8787    1.1801 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7981   -0.3076    0.7573 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1528    0.7631   -0.2530 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6833   -0.1785   -1.3590 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7778   -0.8901   -0.9311 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5418   -1.0117   -1.4616 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8840   -1.8591    1.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6801   -3.3031   -0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4941   -3.0724   -2.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
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  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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
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 27 61  1  0  0  0  0
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M  END

     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242118033D          

 63 66  0  0  0  0            999 V2000
    4.1202   -0.8603    2.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5848   -0.0622   -2.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4383   -1.6692   -3.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2033   -2.3844    0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0630   -1.9699   -1.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1778    3.1905   -2.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9735    2.9245   -2.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3744    4.4169   -2.0947 H   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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
  8  3  1  0  0  0  0
 23  9  1  0  0  0  0
 25  4  1  0  0  0  0
 22 13  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
  3 31  1  1  0  0  0
  4 32  1  1  0  0  0
  5 33  1  6  0  0  0
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  8 35  1  1  0  0  0
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 25 60  1  6  0  0  0
 27 61  1  0  0  0  0
 27 62  1  0  0  0  0
 27 63  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004060

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@@]([H])(C1=C2[C@@]3([H])C([H])([H])[C@@]([H])(OC([H])([H])[H])[C@]4([H])[C@@]([H])(O[H])O[C@@]([H])([C@@]4([H])OC([H])([H])[H])[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]2(C([H])([H])[H])C([H])([H])C1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H36O5/c1-12(11-23)13-6-7-21(2)8-9-22(3)14(17(13)21)10-15(25-4)16-18(26-5)19(22)27-20(16)24/h12,14-16,18-20,23-24H,6-11H2,1-5H3/t12-,14+,15+,16-,18-,19-,20-,21+,22+/m0/s1

> <INCHI_KEY>
BRTUEJWZRSMTSY-LBNQWDEXSA-N

> <FORMULA>
C22H36O5

> <MOLECULAR_WEIGHT>
380.525

> <EXACT_MASS>
380.256274259

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
42.73748306458806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,5R,10R,12R,13S,14S,16S)-8-[(2R)-1-hydroxypropan-2-yl]-12,16-dimethoxy-2,5-dimethyl-15-oxatetracyclo[11.2.1.0^{2,10}.0^{5,9}]hexadec-8-en-14-ol

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
1.886375579666666

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.585446505018684

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.010342051488601

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6641078385369865

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
103.19289999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5R,10R,12R,13S,14S,16S)-8-[(2R)-1-hydroxypropan-2-yl]-12,16-dimethoxy-2,5-dimethyl-15-oxatetracyclo[11.2.1.0^{2,10}.0^{5,9}]hexadec-8-en-14-ol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 63 66  0  0  0  0  0  0  0  0999 V2000
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    0.1886   -1.6580    1.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1981   -2.3976   -1.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2633   -2.5408   -1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0290    0.0324   -0.5473 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6539    1.2252   -0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6801   -3.3031   -0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1089    0.0094   -1.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8346    1.3783    0.9733 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7420    1.1524   -1.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1778    3.1905   -2.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3744    4.4169   -2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
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 13 14  1  6
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 24 25  1  0
 25 26  1  0
 26 27  1  0
  8  3  1  0
 23  9  1  0
 25  4  1  0
 22 13  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  1
  4 32  1  1
  5 33  1  6
  6 34  1  0
  8 35  1  1
 10 36  1  0
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 23 57  1  6
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 25 60  1  6
 27 61  1  0
 27 62  1  0
 27 63  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.120  -0.860   2.566  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.995  -0.879   1.180  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.798  -0.308   0.757  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.153   0.763  -0.253  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.683  -0.179  -1.359  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.778  -0.890  -0.931  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.542  -1.012  -1.462  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.118  -1.270  -0.172  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.640  -1.252  -0.105  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.189  -1.658   1.282  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.198  -2.398  -1.038  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.263  -2.541  -1.122  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.049  -1.277  -1.145  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.351  -0.798  -2.552  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.375  -1.617  -0.510  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.747  -0.325   0.097  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.453   0.377   0.376  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.361   1.491   1.319  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.388   2.572   0.889  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.767   1.167   2.738  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.060   0.741   2.893  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.471  -0.159  -0.333  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.029   0.032  -0.547  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.654   1.225  -0.088  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.975   1.436  -0.850  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.296   2.813  -0.894  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.216   3.325  -2.173  0.00  0.00           C+0
HETATM   28  H   UNK     0       3.337  -1.400   3.096  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.126   0.212   2.870  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.103  -1.268   2.870  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.223   0.027   1.601  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.964   1.414   0.071  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.816   0.358  -2.305  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.494  -0.258  -0.716  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.452  -2.302   0.072  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.476  -0.925   2.057  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.754  -2.594   1.528  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.884  -1.859   1.349  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.603  -2.130  -2.036  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.680  -3.303  -0.620  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.494  -3.072  -2.088  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.641  -3.248  -0.335  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.585  -0.062  -2.897  0.00  0.00           H+0
HETATM   44  H   UNK     0      -2.438  -1.669  -3.206  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.318  -0.254  -2.570  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.203  -2.384   0.269  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.063  -1.970  -1.306  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.415   0.302  -0.532  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.326  -0.539   1.018  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.426   2.083   1.283  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.408   2.183   0.970  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.129   2.772  -0.187  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.192   3.463   1.521  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.105   0.349   3.151  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.642   2.098   3.327  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.119   0.232   3.741  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.109   0.009  -1.682  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.835   1.378   0.973  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.108   2.154  -0.451  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.742   1.152  -1.896  0.00  0.00           H+0
HETATM   61  H   UNK     0       1.178   3.191  -2.543  0.00  0.00           H+0
HETATM   62  H   UNK     0       2.974   2.925  -2.867  0.00  0.00           H+0
HETATM   63  H   UNK     0       2.374   4.417  -2.095  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    8   31                                             
CONECT    4    3    5   25   32                                             
CONECT    5    4    6    7   33                                             
CONECT    6    5   34                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9    3   35                                             
CONECT    9    8   10   11   23                                             
CONECT   10    9   36   37   38                                             
CONECT   11    9   12   39   40                                             
CONECT   12   11   13   41   42                                             
CONECT   13   12   14   15   22                                             
CONECT   14   13   43   44   45                                             
CONECT   15   13   16   46   47                                             
CONECT   16   15   17   48   49                                             
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20   50                                             
CONECT   19   18   51   52   53                                             
CONECT   20   18   21   54   55                                             
CONECT   21   20   56                                                       
CONECT   22   17   23   13                                                  
CONECT   23   22   24    9   57                                             
CONECT   24   23   25   58   59                                             
CONECT   25   24   26    4   60                                             
CONECT   26   25   27                                                       
CONECT   27   26   61   62   63                                             
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    6                                                            
CONECT   35    8                                                            
CONECT   36   10                                                            
CONECT   37   10                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   12                                                            
CONECT   42   12                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   14                                                            
CONECT   46   15                                                            
CONECT   47   15                                                            
CONECT   48   16                                                            
CONECT   49   16                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   19                                                            
CONECT   53   19                                                            
CONECT   54   20                                                            
CONECT   55   20                                                            
CONECT   56   21                                                            
CONECT   57   23                                                            
CONECT   58   24                                                            
CONECT   59   24                                                            
CONECT   60   25                                                            
CONECT   61   27                                                            
CONECT   62   27                                                            
CONECT   63   27                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  132    0
END

RDKit          3D

63 66  0  0  0  0  0  0  0  0999 V2000
    4.1202   -0.8603    2.5662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9953   -0.8787    1.1801 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7981   -0.3076    0.7573 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1528    0.7631   -0.2530 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6833   -0.1785   -1.3590 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7778   -0.8901   -0.9311 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5418   -1.0117   -1.4616 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1184   -1.2698   -0.1717 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6395   -1.2525   -0.1046 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1886   -1.6580    1.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1981   -2.3976   -1.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2633   -2.5408   -1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0494   -1.2767   -1.1451 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3511   -0.7976   -2.5519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3750   -1.6174   -0.5099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7474   -0.3253    0.0971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4526    0.3767    0.3756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3605    1.4909    1.3191 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3881    2.5720    0.8893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7670    1.1668    2.7383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0601    0.7412    2.8928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4710   -0.1587   -0.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0290    0.0324   -0.5473 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6539    1.2252   -0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750    1.4360   -0.8498 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2963    2.8135   -0.8941 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2159    3.3245   -2.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -1.4001    3.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1256    0.2117    2.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1032   -1.2684    2.8700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2232    0.0274    1.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9643    1.4140    0.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8157    0.3576   -2.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4940   -0.2582   -0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4524   -2.3019    0.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4756   -0.9249    2.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7542   -2.5942    1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8840   -1.8591    1.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6025   -2.1304   -2.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6801   -3.3031   -0.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4941   -3.0724   -2.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6405   -3.2484   -0.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848   -0.0622   -2.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4383   -1.6692   -3.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3185   -0.2542   -2.5700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2033   -2.3844    0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0630   -1.9699   -1.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4153    0.3016   -0.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3258   -0.5391    1.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4257    2.0832    1.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4076    2.1830    0.9695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1292    2.7717   -0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1925    3.4634    1.5209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1053    0.3490    3.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6415    2.0984    3.3270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1190    0.2318    3.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1089    0.0094   -1.6817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8346    1.3783    0.9733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1081    2.1539   -0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7420    1.1524   -1.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1778    3.1905   -2.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9735    2.9245   -2.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3744    4.4169   -2.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 17 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  8  3  1  0
 23  9  1  0
 25  4  1  0
 22 13  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  1
  4 32  1  1
  5 33  1  6
  6 34  1  0
  8 35  1  1
 10 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 14 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 18 50  1  1
 19 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 23 57  1  6
 24 58  1  0
 24 59  1  0
 25 60  1  6
 27 61  1  0
 27 62  1  0
 27 63  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₂H₃₆O₅

Average Mass

380.5250 Da

Monoisotopic Mass

380.25627 Da

IUPAC Name

(1R,2R,5R,10R,12R,13S,14S,16S)-8-[(2R)-1-hydroxypropan-2-yl]-12,16-dimethoxy-2,5-dimethyl-15-oxatetracyclo[11.2.1.0^{2,10}.0^{5,9}]hexadec-8-en-14-ol

Traditional Name

(1R,2R,5R,10R,12R,13S,14S,16S)-8-[(2R)-1-hydroxypropan-2-yl]-12,16-dimethoxy-2,5-dimethyl-15-oxatetracyclo[11.2.1.0^{2,10}.0^{5,9}]hexadec-8-en-14-ol

CAS Registry Number

Not Available

SMILES

CO[C@@H]1[C@@H]2OC(O)[C@H]1[C@@H](C[C@@H]1C3=C(CC[C@]3(C)CC[C@@]21C)C(C)CO)OC

InChI Identifier

InChI=1S/C22H36O5/c1-12(11-23)13-6-7-21(2)8-9-22(3)14(17(13)21)10-15(25-4)16-18(26-5)19(22)27-20(16)24/h12,14-16,18-20,23-24H,6-11H2,1-5H3/t12?,14-,15-,16+,18+,19+,20?,21-,22-/m1/s1

InChI Key

BRTUEJWZRSMTSY-LBNQWDEXSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Sarcodon scabrosus	NPAtlas	11866103

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Monosaccharide
Oxolane
Hemiacetal
Oxacycle
Organoheterocyclic compound
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	2.1	ALOGPS
logP	1.89	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	12.01	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.19 m³·mol⁻¹	ChemAxon
Polarizability	42.74 Å³	ChemAxon
Number of Rings	4	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

NPAtlas ID

NPA001405

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8198260

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10022687

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hirota M, Morimura K, Shibata H: Anti-inflammatory compounds from the bitter mushroom, Sarcodon scabrosus. Biosci Biotechnol Biochem. 2002 Jan;66(1):179-84. doi: 10.1271/bbb.66.179. [PubMed:11866103 ]

Showing NP-Card for Neosarcodonin C (NP0004060)

MOL for NP0004060 (Neosarcodonin C)

3D MOL for NP0004060 (Neosarcodonin C)

3D SDF for NP0004060 (Neosarcodonin C)

3D-SDF for NP0004060 (Neosarcodonin C)

PDB for NP0004060 (Neosarcodonin C)

3D PDB for NP0004060 (Neosarcodonin C)

SMILES for NP0004060 (Neosarcodonin C)

INCHI for NP0004060 (Neosarcodonin C)

Structure for NP0004060 (Neosarcodonin C)

3D Structure for NP0004060 (Neosarcodonin C)