NP-MRD: Showing NP-Card for pinusolide (NP0040645)

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Record Information

Version

2.0

Created at

2021-06-20 22:45:09 UTC

Updated at

2021-06-30 00:14:40 UTC

NP-MRD ID

NP0040645

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pinusolide

Provided By

JEOL Database JEOL Logo

Description

Pinusolide belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. pinusolide is found in Agathis macrophylla, Biodata orientalis, Biota orientalis, Pinus armandii, Pinus armandii var.mastersiana , Pinus koraiensis , Pinus sibirica, Pinus sibiruca and Platycladus orientalis . pinusolide was first documented in 2011 (Zaugg, J., et al.). Based on a literature review a small amount of articles have been published on Pinusolide.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212100453D          

 55 57  0  0  0  0            999 V2000
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   -3.7676    1.4450   -1.0961 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


  Mrv1652306212100453D          

 55 57  0  0  0  0            999 V2000
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   -4.4048   -3.6231   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9374   -2.7698   -1.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3009    1.2985    1.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3208   -0.1206    1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177   -0.5347    2.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3671   -1.5877    0.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8788   -0.6879    0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    0.9645    0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0361   -1.2239   -2.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9710   -1.7896   -1.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -1.8943   -1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2403    1.9566   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8928   -0.5268   -1.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6196    0.0663   -0.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6059    2.2649   -0.6758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8971    1.7672   -2.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2279    0.5242   -2.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1630    0.5338   -0.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4885   -1.1170   -1.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  6  0  0  0
 12  6  1  0  0  0  0
  6  8  1  6  0  0  0
 15 17  1  0  0  0  0
  6  7  1  0  0  0  0
  5  4  1  0  0  0  0
  5 32  1  1  0  0  0
  4  3  1  0  0  0  0
  8  9  2  0  0  0  0
  3  2  1  0  0  0  0
  8 10  1  0  0  0  0
 17  2  1  0  0  0  0
 19 20  1  0  0  0  0
 20 24  1  0  0  0  0
  6  5  1  0  0  0  0
 15 14  1  0  0  0  0
 15  5  1  0  0  0  0
 24 23  1  0  0  0  0
 23 22  1  0  0  0  0
 22 21  1  0  0  0  0
 21 20  2  0  0  0  0
 17 18  1  0  0  0  0
 24 25  2  0  0  0  0
  2  1  2  3  0  0  0
 10 11  1  0  0  0  0
 13 41  1  0  0  0  0
 13 42  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
 14 43  1  0  0  0  0
 14 44  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
 17 48  1  1  0  0  0
 19 51  1  0  0  0  0
 19 52  1  0  0  0  0
 18 49  1  0  0  0  0
 18 50  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 16 45  1  0  0  0  0
 16 46  1  0  0  0  0
 16 47  1  0  0  0  0
  7 33  1  0  0  0  0
  7 34  1  0  0  0  0
  7 35  1  0  0  0  0
 22 54  1  0  0  0  0
 22 55  1  0  0  0  0
 21 53  1  0  0  0  0
 11 36  1  0  0  0  0
 11 37  1  0  0  0  0
 11 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0040645

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C1C([H])([H])C([H])([H])[C@@]2([H])[C@](C(=O)OC([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@@]1([H])C([H])([H])C([H])([H])C1=C([H])C([H])([H])OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O4/c1-14-6-9-17-20(2,11-5-12-21(17,3)19(23)24-4)16(14)8-7-15-10-13-25-18(15)22/h10,16-17H,1,5-9,11-13H2,2-4H3/t16-,17+,20+,21-/m0/s1

> <INCHI_KEY>
WTKBZJAWPZXKJU-NLEAXPPASA-N

> <FORMULA>
C21H30O4

> <MOLECULAR_WEIGHT>
346.467

> <EXACT_MASS>
346.214409446

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.99812953296021

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-2,5-dihydrofuran-3-yl)ethyl]-decahydronaphthalene-1-carboxylate

> <ALOGPS_LOGP>
4.56

> <JCHEM_LOGP>
4.586394158333334

> <ALOGPS_LOGS>
-5.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.394091497512228

> <JCHEM_PKA_STRONGEST_BASIC>
-6.670696523422023

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
96.76509999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.32e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5H-furan-3-yl)ethyl]-hexahydro-2H-naphthalene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
    1.9772    0.8301   -4.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1570    1.2592   -3.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0735    2.0590   -3.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3308    1.3245   -2.9963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2719    0.9783   -1.4895 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6159    0.4340   -0.8803 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7676    1.4450   -1.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1126   -0.8631   -1.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1425   -1.0505   -2.7574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823   -1.7620   -0.6384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0777   -2.9741   -1.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4256    0.2980    0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2168   -0.5407    1.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0730   -0.0078    0.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0274    0.1507   -1.1164 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0437   -1.2587   -1.7567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2951    0.9761   -1.6139 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6628    0.3785   -1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8155    1.3904   -1.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1180    0.7995   -0.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1683    0.4454   -1.6364 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2562   -0.0720   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7450    0.0243    0.5393 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4869    0.5445    0.5010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7824    0.7640    1.4692 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8507    0.2179   -3.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7817    1.0651   -5.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0125    3.0427   -2.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1450    2.2454   -4.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1884    1.9698   -3.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    0.4233   -3.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1311    1.9547   -0.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6640    1.1403   -0.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0644    1.5153   -2.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4892    2.4476   -0.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2870   -3.4886   -1.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4048   -3.6231   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9374   -2.7698   -1.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3009    1.2985    1.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3208   -0.1206    1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177   -0.5347    2.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3671   -1.5877    0.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8788   -0.6879    0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    0.9645    0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0361   -1.2239   -2.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9710   -1.7896   -1.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -1.8943   -1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2403    1.9566   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8928   -0.5268   -1.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6196    0.0663   -0.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6059    2.2649   -0.6758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8971    1.7672   -2.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2279    0.5242   -2.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1630    0.5338   -0.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4885   -1.1170   -1.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 13 12  1  0
 13 14  1  0
 15 16  1  6
 12  6  1  0
  6  8  1  6
 15 17  1  0
  6  7  1  0
  5  4  1  0
  5 32  1  1
  4  3  1  0
  8  9  2  0
  3  2  1  0
  8 10  1  0
 17  2  1  0
 19 20  1  0
 20 24  1  0
  6  5  1  0
 15 14  1  0
 15  5  1  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  2  0
 17 18  1  0
 24 25  2  0
  2  1  2  3
 10 11  1  0
 13 41  1  0
 13 42  1  0
 12 39  1  0
 12 40  1  0
 14 43  1  0
 14 44  1  0
  4 30  1  0
  4 31  1  0
  3 28  1  0
  3 29  1  0
 17 48  1  1
 19 51  1  0
 19 52  1  0
 18 49  1  0
 18 50  1  0
  1 26  1  0
  1 27  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
 22 54  1  0
 22 55  1  0
 21 53  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       1.977   0.830  -4.088  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.157   1.259  -3.113  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.074   2.059  -3.459  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.331   1.325  -2.996  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.272   0.978  -1.490  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.616   0.434  -0.880  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.768   1.445  -1.096  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.113  -0.863  -1.547  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.143  -1.050  -2.757  0.00  0.00           O+0
HETATM   10  O   UNK     0      -3.582  -1.762  -0.638  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.078  -2.974  -1.209  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.426   0.298   0.653  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.217  -0.541   1.044  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.073  -0.008   0.429  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.027   0.151  -1.116  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.044  -1.259  -1.757  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.295   0.976  -1.614  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.663   0.379  -1.183  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.816   1.390  -1.304  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.118   0.800  -0.898  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.168   0.445  -1.636  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.256  -0.072  -0.788  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.745   0.024   0.539  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.487   0.545   0.501  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.782   0.764   1.469  0.00  0.00           O+0
HETATM   26  H   UNK     0       2.851   0.218  -3.898  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.782   1.065  -5.131  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.013   3.043  -2.978  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.145   2.245  -4.538  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.188   1.970  -3.211  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.453   0.423  -3.604  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.131   1.955  -0.995  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.664   1.140  -0.542  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.064   1.515  -2.148  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.489   2.448  -0.753  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.287  -3.489  -1.764  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.405  -3.623  -0.392  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.937  -2.770  -1.854  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.301   1.299   1.091  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.321  -0.121   1.130  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.118  -0.535   2.136  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.367  -1.588   0.762  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.879  -0.688   0.727  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.298   0.965   0.887  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.036  -1.224  -2.847  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.971  -1.790  -1.516  0.00  0.00           H+0
HETATM   47  H   UNK     0      -0.766  -1.894  -1.394  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.240   1.957  -1.115  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.893  -0.527  -1.758  0.00  0.00           H+0
HETATM   50  H   UNK     0       2.620   0.066  -0.136  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.606   2.265  -0.676  0.00  0.00           H+0
HETATM   52  H   UNK     0       3.897   1.767  -2.329  0.00  0.00           H+0
HETATM   53  H   UNK     0       6.228   0.524  -2.712  0.00  0.00           H+0
HETATM   54  H   UNK     0       8.163   0.534  -0.871  0.00  0.00           H+0
HETATM   55  H   UNK     0       7.489  -1.117  -1.012  0.00  0.00           H+0
CONECT    1    2   26   27                                                  
CONECT    2    3   17    1                                                  
CONECT    3    4    2   28   29                                             
CONECT    4    5    3   30   31                                             
CONECT    5    4   32    6   15                                             
CONECT    6   12    8    7    5                                             
CONECT    7    6   33   34   35                                             
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   36   37   38                                             
CONECT   12   13    6   39   40                                             
CONECT   13   12   14   41   42                                             
CONECT   14   13   15   43   44                                             
CONECT   15   16   17   14    5                                             
CONECT   16   15   45   46   47                                             
CONECT   17   15    2   18   48                                             
CONECT   18   19   17   49   50                                             
CONECT   19   18   20   51   52                                             
CONECT   20   19   24   21                                                  
CONECT   21   22   20   53                                                  
CONECT   22   23   21   54   55                                             
CONECT   23   24   22                                                       
CONECT   24   20   23   25                                                  
CONECT   25   24                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    3                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    7                                                            
CONECT   34    7                                                            
CONECT   35    7                                                            
CONECT   36   11                                                            
CONECT   37   11                                                            
CONECT   38   11                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   13                                                            
CONECT   42   13                                                            
CONECT   43   14                                                            
CONECT   44   14                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   16                                                            
CONECT   48   17                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   19                                                            
CONECT   52   19                                                            
CONECT   53   21                                                            
CONECT   54   22                                                            
CONECT   55   22                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

RDKit          3D

55 57  0  0  0  0  0  0  0  0999 V2000
    1.9772    0.8301   -4.0878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1570    1.2592   -3.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0735    2.0590   -3.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3308    1.3245   -2.9963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2719    0.9783   -1.4895 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6159    0.4340   -0.8803 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7676    1.4450   -1.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1126   -0.8631   -1.5472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1425   -1.0505   -2.7574 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5823   -1.7620   -0.6384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0777   -2.9741   -1.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4256    0.2980    0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2168   -0.5407    1.0440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0730   -0.0078    0.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0274    0.1507   -1.1164 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0437   -1.2587   -1.7567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2951    0.9761   -1.6139 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6628    0.3785   -1.1834 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8155    1.3904   -1.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1180    0.7995   -0.8979 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1683    0.4454   -1.6364 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2562   -0.0720   -0.7881 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7450    0.0243    0.5393 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4869    0.5445    0.5010 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7824    0.7640    1.4692 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8507    0.2179   -3.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7817    1.0651   -5.1308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0125    3.0427   -2.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1450    2.2454   -4.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1884    1.9698   -3.2110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    0.4233   -3.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1311    1.9547   -0.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6640    1.1403   -0.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0644    1.5153   -2.1480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4892    2.4476   -0.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2870   -3.4886   -1.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4048   -3.6231   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9374   -2.7698   -1.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3009    1.2985    1.0906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3208   -0.1206    1.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1177   -0.5347    2.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3671   -1.5877    0.7618 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8788   -0.6879    0.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2984    0.9645    0.8870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0361   -1.2239   -2.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9710   -1.7896   -1.5157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -1.8943   -1.3940 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2403    1.9566   -1.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8928   -0.5268   -1.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6196    0.0663   -0.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6059    2.2649   -0.6758 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8971    1.7672   -2.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2279    0.5242   -2.7119 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1630    0.5338   -0.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4885   -1.1170   -1.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 13 12  1  0
 13 14  1  0
 15 16  1  6
 12  6  1  0
  6  8  1  6
 15 17  1  0
  6  7  1  0
  5  4  1  0
  5 32  1  1
  4  3  1  0
  8  9  2  0
  3  2  1  0
  8 10  1  0
 17  2  1  0
 19 20  1  0
 20 24  1  0
  6  5  1  0
 15 14  1  0
 15  5  1  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 20  2  0
 17 18  1  0
 24 25  2  0
  2  1  2  3
 10 11  1  0
 13 41  1  0
 13 42  1  0
 12 39  1  0
 12 40  1  0
 14 43  1  0
 14 44  1  0
  4 30  1  0
  4 31  1  0
  3 28  1  0
  3 29  1  0
 17 48  1  1
 19 51  1  0
 19 52  1  0
 18 49  1  0
 18 50  1  0
  1 26  1  0
  1 27  1  0
 16 45  1  0
 16 46  1  0
 16 47  1  0
  7 33  1  0
  7 34  1  0
  7 35  1  0
 22 54  1  0
 22 55  1  0
 21 53  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Value	Source
Methyl (1S,4ar,5S,8ar)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-2,5-dihydrofuran-3-yl)ethyl]-decahydronaphthalene-1-carboxylic acid	Generator

Chemical Formula

C₂₁H₃₀O₄

Average Mass

346.4670 Da

Monoisotopic Mass

346.21441 Da

IUPAC Name

methyl (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-2,5-dihydrofuran-3-yl)ethyl]-decahydronaphthalene-1-carboxylate

Traditional Name

methyl (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[2-(2-oxo-5H-furan-3-yl)ethyl]-hexahydro-2H-naphthalene-1-carboxylate

CAS Registry Number

Not Available

SMILES

[H]C([H])=C1C([H])([H])C([H])([H])[C@@]2([H])[C@](C(=O)OC([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]2(C([H])([H])[H])[C@@]1([H])C([H])([H])C([H])([H])C1=C([H])C([H])([H])OC1=O

InChI Identifier

InChI=1S/C21H30O4/c1-14-6-9-17-20(2,11-5-12-21(17,3)19(23)24-4)16(14)8-7-15-10-13-25-18(15)22/h10,16-17H,1,5-9,11-13H2,2-4H3/t16-,17+,20+,21-/m0/s1

InChI Key

WTKBZJAWPZXKJU-NLEAXPPASA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Agathis macrophylla	LOTUS Database	35616633
Biodata orientalis	-	KNApSAcK
Biota orientalis	JEOL database	Zaugg, J., et al, J. Nat. Prod. 74, 1764 (2011)
Pinus armandii	LOTUS Database	35616633
Pinus armandii var.mastersiana	Plant	KNApSAcK
Pinus koraiensis	Plant	KNApSAcK
Pinus sibirica	Plant	KNApSAcK
Pinus sibiruca	Plant	KNApSAcK
Platycladus orientalis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Clerodane diterpenoid
Diterpenoid
2-furanone
Dicarboxylic acid or derivatives
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

diterpene lactone (CHEBI:69237 )

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	4.56	ALOGPS
logP	4.59	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	13.39	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	96.77 m³·mol⁻¹	ChemAxon
Polarizability	39 Å³	ChemAxon
Number of Rings	3	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

HMDB ID

HMDB0035130

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00022771

Chemspider ID

142040

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

161721

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1402371

References

General References

Zaugg, J., et al. (2011). Zaugg, J., et al, J. Nat. Prod. 74, 1764 (2011). J. Nat. Prod..

Showing NP-Card for pinusolide (NP0040645)

MOL for NP0040645 (pinusolide)

3D MOL for NP0040645 (pinusolide)

3D SDF for NP0040645 (pinusolide)

3D-SDF for NP0040645 (pinusolide)

PDB for NP0040645 (pinusolide)

3D PDB for NP0040645 (pinusolide)

SMILES for NP0040645 (pinusolide)

INCHI for NP0040645 (pinusolide)

Structure for NP0040645 (pinusolide)

3D Structure for NP0040645 (pinusolide)