NP-MRD: Showing NP-Card for sikkimenoid C (NP0043252)

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Record Information

Version

1.0

Created at

2021-06-21 00:42:50 UTC

Updated at

2021-06-30 00:18:50 UTC

NP-MRD ID

NP0043252

Secondary Accession Numbers

None

Natural Product Identification

Common Name

sikkimenoid C

Provided By

JEOL Database JEOL Logo

Description

Sikkimenoid C belongs to the class of organic compounds known as jatropholane and crotopholane diterpenoids. These are diterpenoids with a structure based either on the jatropholane or the crotopholane skeleton. Jatropholanes arise by 5,13- and 6,10-cyclisation of a casbane precursor. Subsequent cleavage of the 2,15-cyclopropane bond affords crotofolane. sikkimenoid C is found in Euphorbia sikkimensis. It was first documented in 2018 (PMID: 29493237). Based on a literature review very few articles have been published on Sikkimenoid C.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102423D          

 49 52  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306212102423D          

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  6 21  1  0  0  0  0
 16 14  1  0  0  0  0
 14 13  1  0  0  0  0
 13 12  2  0  0  0  0
  8  9  1  0  0  0  0
 20  7  1  0  0  0  0
  7 32  1  1  0  0  0
  7  6  1  0  0  0  0
 16 17  1  0  0  0  0
 12 10  1  0  0  0  0
 21 22  1  1  0  0  0
 20  2  1  0  0  0  0
 20 43  1  6  0  0  0
 13 20  1  0  0  0  0
  6 31  1  1  0  0  0
  2  3  1  0  0  0  0
  5 30  1  1  0  0  0
  7  8  1  0  0  0  0
 21 23  1  0  0  0  0
  5  4  1  0  0  0  0
 16 18  1  6  0  0  0
  8 33  1  6  0  0  0
 19 41  1  0  0  0  0
 19 42  1  0  0  0  0
  3 26  1  0  0  0  0
  3 27  1  0  0  0  0
  4 28  1  0  0  0  0
  4 29  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  9 34  1  0  0  0  0
  9 35  1  0  0  0  0
  9 36  1  0  0  0  0
 17 37  1  0  0  0  0
 17 38  1  0  0  0  0
 17 39  1  0  0  0  0
 22 44  1  0  0  0  0
 22 45  1  0  0  0  0
 22 46  1  0  0  0  0
 23 47  1  0  0  0  0
 23 48  1  0  0  0  0
 23 49  1  0  0  0  0
 18 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043252

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1(C(=O)C2=C(C(=O)[C@@]([H])(C([H])([H])[H])[C@]3([H])[C@]4([H])[C@]([H])(C([H])([H])C([H])([H])C(=C([H])[H])[C@@]23[H])C4(C([H])([H])[H])C([H])([H])[H])C1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O3/c1-9-6-7-12-16(19(12,3)4)14-10(2)17(21)11-8-20(5,23)18(22)15(11)13(9)14/h10,12-14,16,23H,1,6-8H2,2-5H3/t10-,12-,13+,14-,16-,20-/m0/s1

> <INCHI_KEY>
AKYCTHTXCPVVOB-STPYIFJPSA-N

> <FORMULA>
C20H26O3

> <MOLECULAR_WEIGHT>
314.425

> <EXACT_MASS>
314.188194697

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
35.58342194972913

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4S,8S,9R,10R,12S)-4-hydroxy-4,8,11,11-tetramethyl-15-methylidenetetracyclo[7.6.0.0^{2,6}.0^{10,12}]pentadec-2(6)-ene-3,7-dione

> <ALOGPS_LOGP>
2.75

> <JCHEM_LOGP>
3.1793765716666664

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.61111759036148

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.158415090468619

> <JCHEM_PKA_STRONGEST_BASIC>
-3.604309161024278

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
89.39359999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,8S,9R,10R,12S)-4-hydroxy-4,8,11,11-tetramethyl-15-methylidenetetracyclo[7.6.0.0^{2,6}.0^{10,12}]pentadec-2(6)-ene-3,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 49 52  0  0  0  0  0  0  0  0999 V2000
   -3.8573    0.1304   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7152   -0.2523    0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7044   -1.5125    1.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6798   -1.1918    2.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3098   -0.8046    3.1585 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5877    0.4277    2.6517 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1935    1.3341    1.5872 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2913    2.5883    1.4005 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2691    3.4754    2.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7185    3.4122    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7178    4.6389    0.1565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0214    2.6630   -1.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2610    1.3562   -0.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3450    0.9037   -2.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4581   -0.2683   -2.6835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2946    2.0777   -3.3273 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2206    1.8807   -4.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5630    2.2287   -3.9563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0099    3.2692   -2.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3815    0.5056    0.2631 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0452    0.3560    4.1097 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0288    0.1433    5.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1875    1.1990    4.6221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9352    1.0293   -0.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7700   -0.4516   -0.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6037   -2.1066    0.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8530   -2.1432    0.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9770   -2.0907    3.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4355   -0.4345    2.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6978   -1.6973    3.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4752    0.2828    2.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1805    1.6946    1.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423    2.2710    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2771    3.8146    2.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3465    4.3672    2.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1547    2.9480    3.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650    1.7141   -3.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1641    2.7518   -5.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4513    1.0172   -5.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7648    1.3761   -4.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7756    4.0474   -2.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0297    3.7175   -2.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5751   -0.2380    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4516    1.1039    5.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8499   -0.4771    4.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3908   -0.3533    6.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091    2.1439    5.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7049    0.6719    5.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9322    1.4480    3.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  8 10  1  0
 14 15  2  0
 12 19  1  0
 10 11  2  0
 19 16  1  0
  2  1  2  3
  5  6  1  0
 21  5  1  0
  6 21  1  0
 16 14  1  0
 14 13  1  0
 13 12  2  0
  8  9  1  0
 20  7  1  0
  7 32  1  1
  7  6  1  0
 16 17  1  0
 12 10  1  0
 21 22  1  1
 20  2  1  0
 20 43  1  6
 13 20  1  0
  6 31  1  1
  2  3  1  0
  5 30  1  1
  7  8  1  0
 21 23  1  0
  5  4  1  0
 16 18  1  6
  8 33  1  6
 19 41  1  0
 19 42  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  1 24  1  0
  1 25  1  0
  9 34  1  0
  9 35  1  0
  9 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 18 40  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      -3.857   0.130  -0.258  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.715  -0.252   0.346  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.704  -1.513   1.191  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.680  -1.192   2.688  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.310  -0.805   3.159  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.588   0.428   2.652  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.194   1.334   1.587  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.291   2.588   1.401  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.269   3.475   2.648  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.719   3.412   0.186  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.718   4.639   0.157  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.021   2.663  -1.040  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.261   1.356  -0.954  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.345   0.904  -2.352  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.458  -0.268  -2.684  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.295   2.078  -3.327  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.221   1.881  -4.387  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.563   2.229  -3.956  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.010   3.269  -2.402  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.381   0.506   0.263  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.045   0.356   4.110  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.029   0.143   5.154  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.188   1.199   4.622  0.00  0.00           C+0
HETATM   24  H   UNK     0      -3.935   1.029  -0.861  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.770  -0.452  -0.161  0.00  0.00           H+0
HETATM   26  H   UNK     0      -3.604  -2.107   0.983  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.853  -2.143   0.907  0.00  0.00           H+0
HETATM   28  H   UNK     0      -2.977  -2.091   3.242  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.436  -0.435   2.917  0.00  0.00           H+0
HETATM   30  H   UNK     0      -0.698  -1.697   3.274  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.475   0.283   2.460  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.180   1.695   1.902  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.742   2.271   1.203  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.277   3.815   2.910  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.347   4.367   2.486  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.155   2.948   3.507  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.765   1.714  -3.939  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.164   2.752  -5.049  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.451   1.017  -5.021  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.765   1.376  -4.388  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.776   4.047  -2.490  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.030   3.717  -2.599  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.575  -0.238   0.187  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.452   1.104   5.466  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.850  -0.477   4.778  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.391  -0.353   6.035  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.809   2.144   5.026  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.705   0.672   5.431  0.00  0.00           H+0
HETATM   49  H   UNK     0      -2.932   1.448   3.864  0.00  0.00           H+0
CONECT    1    2   24   25                                                  
CONECT    2    1   20    3                                                  
CONECT    3    4    2   26   27                                             
CONECT    4    3    5   28   29                                             
CONECT    5    6   21   30    4                                             
CONECT    6    5   21    7   31                                             
CONECT    7   20   32    6    8                                             
CONECT    8   10    9    7   33                                             
CONECT    9    8   34   35   36                                             
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   19   13   10                                                  
CONECT   13   14   12   20                                                  
CONECT   14   15   16   13                                                  
CONECT   15   14                                                            
CONECT   16   19   14   17   18                                             
CONECT   17   16   37   38   39                                             
CONECT   18   16   40                                                       
CONECT   19   12   16   41   42                                             
CONECT   20    7    2   43   13                                             
CONECT   21    5    6   22   23                                             
CONECT   22   21   44   45   46                                             
CONECT   23   21   47   48   49                                             
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    3                                                            
CONECT   27    3                                                            
CONECT   28    4                                                            
CONECT   29    4                                                            
CONECT   30    5                                                            
CONECT   31    6                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35    9                                                            
CONECT   36    9                                                            
CONECT   37   17                                                            
CONECT   38   17                                                            
CONECT   39   17                                                            
CONECT   40   18                                                            
CONECT   41   19                                                            
CONECT   42   19                                                            
CONECT   43   20                                                            
CONECT   44   22                                                            
CONECT   45   22                                                            
CONECT   46   22                                                            
CONECT   47   23                                                            
CONECT   48   23                                                            
CONECT   49   23                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  104    0
END

RDKit          3D

49 52  0  0  0  0  0  0  0  0999 V2000
   -3.8573    0.1304   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7152   -0.2523    0.3458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7044   -1.5125    1.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6798   -1.1918    2.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3098   -0.8046    3.1585 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5877    0.4277    2.6517 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1935    1.3341    1.5872 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2913    2.5883    1.4005 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2691    3.4754    2.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7185    3.4122    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7178    4.6389    0.1565 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0214    2.6630   -1.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2610    1.3562   -0.9544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3450    0.9037   -2.3524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4581   -0.2683   -2.6835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2946    2.0777   -3.3273 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2206    1.8807   -4.3867 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5630    2.2287   -3.9563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0099    3.2692   -2.4019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3815    0.5056    0.2631 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0452    0.3560    4.1097 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0288    0.1433    5.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1875    1.1990    4.6221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9352    1.0293   -0.8610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7700   -0.4516   -0.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6037   -2.1066    0.9833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8530   -2.1432    0.9074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9770   -2.0907    3.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4355   -0.4345    2.9168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6978   -1.6973    3.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4752    0.2828    2.4602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1805    1.6946    1.9018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423    2.2710    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2771    3.8146    2.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3465    4.3672    2.4860 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1547    2.9480    3.5071 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650    1.7141   -3.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1641    2.7518   -5.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4513    1.0172   -5.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7648    1.3761   -4.3877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7756    4.0474   -2.4897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0297    3.7175   -2.5994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5751   -0.2380    0.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4516    1.1039    5.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8499   -0.4771    4.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3908   -0.3533    6.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8091    2.1439    5.0261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7049    0.6719    5.4310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9322    1.4480    3.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  8 10  1  0
 14 15  2  0
 12 19  1  0
 10 11  2  0
 19 16  1  0
  2  1  2  3
  5  6  1  0
 21  5  1  0
  6 21  1  0
 16 14  1  0
 14 13  1  0
 13 12  2  0
  8  9  1  0
 20  7  1  0
  7 32  1  1
  7  6  1  0
 16 17  1  0
 12 10  1  0
 21 22  1  1
 20  2  1  0
 20 43  1  6
 13 20  1  0
  6 31  1  1
  2  3  1  0
  5 30  1  1
  7  8  1  0
 21 23  1  0
  5  4  1  0
 16 18  1  6
  8 33  1  6
 19 41  1  0
 19 42  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  1 24  1  0
  1 25  1  0
  9 34  1  0
  9 35  1  0
  9 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 23 48  1  0
 23 49  1  0
 18 40  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₀H₂₆O₃

Average Mass

314.4250 Da

Monoisotopic Mass

314.18819 Da

IUPAC Name

(1S,4S,8S,9R,10R,12S)-4-hydroxy-4,8,11,11-tetramethyl-15-methylidenetetracyclo[7.6.0.0^{2,6}.0^{10,12}]pentadec-2(6)-ene-3,7-dione

Traditional Name

(1S,4S,8S,9R,10R,12S)-4-hydroxy-4,8,11,11-tetramethyl-15-methylidenetetracyclo[7.6.0.0^{2,6}.0^{10,12}]pentadec-2(6)-ene-3,7-dione

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1(C(=O)C2=C(C(=O)[C@@]([H])(C([H])([H])[H])[C@]3([H])[C@]4([H])[C@]([H])(C([H])([H])C([H])([H])C(=C([H])[H])[C@@]23[H])C4(C([H])([H])[H])C([H])([H])[H])C1([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C20H26O3/c1-9-6-7-12-16(19(12,3)4)14-10(2)17(21)11-8-20(5,23)18(22)15(11)13(9)14/h10,12-14,16,23H,1,6-8H2,2-5H3/t10-,12-,13+,14-,16-,20-/m0/s1

InChI Key

AKYCTHTXCPVVOB-STPYIFJPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, 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, 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, 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
Euphorbia sikkimensis	JEOL database	Yang, D. -S., et al, J. Nat. Prod. 76, 265 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as jatropholane and crotopholane diterpenoids. These are diterpenoids with a structure based either on the jatropholane or the crotopholane skeleton. Jatropholanes arise by 5,13- and 6,10-cyclisation of a casbane precursor. Subsequent cleavage of the 2,15-cyclopropane bond affords crotofolane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Jatropholane and crotopholane diterpenoids

Alternative Parents

Substituents

Jatropholane or crotopholane diterpenoid
Cyclohexenone
Acyloin
Tertiary alcohol
Cyclic alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.75	ALOGPS
logP	3.18	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	13.16	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	89.39 m³·mol⁻¹	ChemAxon
Polarizability	35.58 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29416051

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71579215

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Remy S, Olivon F, Desrat S, Blanchard F, Eparvier V, Leyssen P, Neyts J, Roussi F, Touboul D, Litaudon M: Structurally Diverse Diterpenoids from Sandwithia guyanensis. J Nat Prod. 2018 Apr 27;81(4):901-912. doi: 10.1021/acs.jnatprod.7b01025. Epub 2018 Mar 1. [PubMed:29493237 ]
Yang, D. -S., et al. (2013). Yang, D. -S., et al, J. Nat. Prod. 76, 265 (2013). J. Nat. Prod..

Showing NP-Card for sikkimenoid C (NP0043252)

MOL for NP0043252 (sikkimenoid C)

3D MOL for NP0043252 (sikkimenoid C)

3D SDF for NP0043252 (sikkimenoid C)

3D-SDF for NP0043252 (sikkimenoid C)

PDB for NP0043252 (sikkimenoid C)

3D PDB for NP0043252 (sikkimenoid C)

SMILES for NP0043252 (sikkimenoid C)

INCHI for NP0043252 (sikkimenoid C)

Structure for NP0043252 (sikkimenoid C)

3D Structure for NP0043252 (sikkimenoid C)