NP-MRD: Showing NP-Card for Cebellin F (NP0044132)

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Record Information

Version

1.0

Created at

2021-11-12 23:51:55 UTC

Updated at

2021-11-26 17:45:47 UTC

NP-MRD ID

NP0044132

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cebellin F

Description

Cebellin F belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Cebellin F is found in Centaurea scoparia and Psephellus bellus. It was first documented in 2005 (PMID: 16276969). Based on a literature review very few articles have been published on Cebellin F (PMID: 30634079).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100512D          

 30 32  0  0  1  0            999 V2000
    1.7100    0.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -0.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746   -1.0076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6996   -1.0076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2140   -1.6526    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0304   -2.4569    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6754   -2.9713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5524   -3.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1974   -4.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0745   -5.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7195   -5.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5965   -6.4474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9654   -4.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -4.0885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871   -2.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438   -2.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988   -2.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602   -1.6526    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5878   -1.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -0.5386    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0202   -0.0242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389   -2.1954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864   -1.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6749   -1.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493   -0.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5944   -0.0242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541   -0.3191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8352   -2.1954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3416   -1.7509    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2655   -0.2811    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
  8 14  2  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  6  0  0  0
 18 22  1  1  0  0  0
  5 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  4 27  1  0  0  0  0
  5 28  1  1  0  0  0
  4 29  1  6  0  0  0
  3 30  1  1  0  0  0
M  END

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
   -0.9698    0.1869    3.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0902    0.7602    2.1185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1988    1.0713    1.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3898    0.2682    0.1839 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7420    0.1156   -0.0774 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3726   -1.1280   -0.0228 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6733   -2.1089    0.2708 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8098   -1.2660   -0.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4485   -2.5963   -0.2390 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5611   -0.2319   -0.6146 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9965   -0.2510   -0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6025   -1.4800   -0.8549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4446    0.8655   -0.8991 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1412    0.3284   -2.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0007    0.1392   -2.8766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4428    0.0114   -2.8299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6741   -0.6389   -3.8853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317    0.5740   -1.9955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8846    0.4548   -0.6985 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6233    1.3535    0.2312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0961    1.1094    0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8081    1.5687   -0.9962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6243    0.2606    1.1123 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.3889   -0.8022    0.6447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3628   -0.2138    1.8000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4667    0.9856    1.6776 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8304   -0.0888    3.8840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0079   -0.0206    3.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2425    2.1365    1.1678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0685    0.8542    2.1048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0351   -0.7541    0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2071   -2.6886    0.5653 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6595   -3.3473    0.0194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8240   -2.9276   -1.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0639    0.7296   -0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4923    0.5108   -0.2676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1533    0.1309   -1.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4871   -1.4093   -0.3979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4534    1.9789   -0.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -0.2685   -3.8651 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9370    0.4039   -2.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9810   -0.6138   -0.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3444    2.3949    0.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3343    2.1770   -1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8590    1.3494   -1.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1887    0.9225    1.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9794   -1.0829    1.3957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6552   -0.4109    2.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9586   -1.1204    1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9396    1.8080    2.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  2  3
 21 20  1  0
 20 19  1  0
 19 13  1  0
 13  4  1  0
  4  5  1  0
  5  6  1  0
  6  8  1  0
  8 10  2  0
 10 11  1  0
 11 12  1  0
  8  9  1  0
  6  7  2  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 26  1  0
 26 25  1  0
 25 23  1  0
 23 24  1  0
 13 14  1  0
 14 15  2  3
 14 16  1  0
 16 17  2  0
 16 18  1  0
 23 21  1  0
 26 20  1  0
 18 19  1  0
 22 44  1  0
 22 45  1  0
 20 43  1  1
 19 42  1  1
 13 39  1  6
  4 31  1  1
 10 35  1  0
 11 36  1  0
 11 37  1  0
 12 38  1  0
  9 32  1  0
  9 33  1  0
  9 34  1  0
  3 29  1  0
  3 30  1  0
  1 27  1  0
  1 28  1  0
 26 50  1  1
 25 48  1  0
 25 49  1  0
 23 46  1  1
 24 47  1  0
 15 40  1  0
 15 41  1  0
M  END


  Mrv1652311132100512D          

 30 32  0  0  1  0            999 V2000
    1.7100    0.4533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -0.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746   -1.0076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6996   -1.0076    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2140   -1.6526    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0304   -2.4569    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6754   -2.9713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5524   -3.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1974   -4.3015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0745   -5.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7195   -5.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5965   -6.4474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9654   -4.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845   -4.0885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871   -2.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438   -2.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988   -2.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602   -1.6526    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5878   -1.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -0.5386    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0202   -0.0242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7389   -2.1954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864   -1.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6749   -1.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493   -0.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5944   -0.0242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541   -0.3191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8352   -2.1954    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3416   -1.7509    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2655   -0.2811    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  6  7  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
  8 14  2  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  3 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  1  6  0  0  0
 18 22  1  1  0  0  0
  5 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
  4 27  1  0  0  0  0
  5 28  1  1  0  0  0
  4 29  1  6  0  0  0
  3 30  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044132

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@H](O)C(=C)[C@]1([H])[C@@]1([H])OC(=O)C(=C)[C@]1([H])[C@H](CC2=C)OC(=O)C(\C)=C\CO

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O6/c1-9(5-6-21)19(23)25-15-7-10(2)13-8-14(22)11(3)16(13)18-17(15)12(4)20(24)26-18/h5,13-18,21-22H,2-4,6-8H2,1H3/b9-5+/t13-,14-,15-,16-,17+,18+/m0/s1

> <INCHI_KEY>
CILZKZHKUCDCRP-RAHDRTFYSA-N

> <FORMULA>
C20H24O6

> <MOLECULAR_WEIGHT>
360.406

> <EXACT_MASS>
360.157288493

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
38.000731059027785

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl (2E)-4-hydroxy-2-methylbut-2-enoate

> <ALOGPS_LOGP>
0.97

> <JCHEM_LOGP>
1.4314484283333324

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.608601896947015

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.555205204204825

> <JCHEM_PKA_STRONGEST_BASIC>
-2.55219929379004

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
94.6621

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2E)-4-hydroxy-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0       3.192   0.846   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.651  -0.596   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.499  -1.881   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.039  -1.881   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.999  -3.085   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.657  -4.586   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.861  -5.546   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.631  -7.069   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.835  -8.029   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.606  -9.552   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.810 -10.512   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.580 -12.035   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.269  -7.467   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.198  -7.632   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.269  -5.254   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.882  -4.586   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.678  -5.546   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.539  -3.085   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.097  -2.544   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.166  -1.005   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.038  -0.045   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       1.379  -4.098   0.000  0.00  0.00           H+0
HETATM   23  C   UNK     0       7.441  -2.544   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.726  -3.392   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.372  -1.005   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.576  -0.045   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.888  -0.596   0.000  0.00  0.00           O+0
HETATM   28  H   UNK     0       7.159  -4.098   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.371  -3.268   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.229  -0.525   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4   18   30                                             
CONECT    4    3    5   27   29                                             
CONECT    5    4    6   23   28                                             
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    9                                                            
CONECT   14    8                                                            
CONECT   15    6   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    3   19   22                                             
CONECT   19   18   20                                                       
CONECT   20   19    2   21                                                  
CONECT   21   20                                                            
CONECT   22   18                                                            
CONECT   23    5   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    4                                                       
CONECT   28    5                                                            
CONECT   29    4                                                            
CONECT   30    3                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₆

Average Mass

360.4060 Da

Monoisotopic Mass

360.15729 Da

IUPAC Name

(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-dodecahydroazuleno[4,5-b]furan-4-yl (2E)-4-hydroxy-2-methylbut-2-enoate

Traditional Name

(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-octahydroazuleno[4,5-b]furan-4-yl (2E)-4-hydroxy-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@H](O)C(=C)[C@]1([H])[C@@]1([H])OC(=O)C(=C)[C@]1([H])[C@H](CC2=C)OC(=O)C(\C)=C\CO

InChI Identifier

InChI=1S/C20H24O6/c1-9(5-6-21)19(23)25-15-7-10(2)13-8-14(22)11(3)16(13)18-17(15)12(4)20(24)26-18/h5,13-18,21-22H,2-4,6-8H2,1H3/b9-5+/t13-,14-,15-,16-,17+,18+/m0/s1

InChI Key

CILZKZHKUCDCRP-RAHDRTFYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Dimethylsulfoxide-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Centaurea scoparia	LOTUS Database	35616633
Psephellus bellus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Sesquiterpenoid
Guaiane sesquiterpenoid
Fatty acid ester
Fatty acyl
Gamma butyrolactone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	0.97	ALOGPS
logP	1.43	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	14.56	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.66 m³·mol⁻¹	ChemAxon
Polarizability	38 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101705723

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nawrot J, Budzianowski J, Nowak G: Phytochemical profiles of the leaves of Stizolophus balsamita and Psephellus sibiricus and their chemotaxonomic implications. Phytochemistry. 2019 Mar;159:172-178. doi: 10.1016/j.phytochem.2018.12.022. Epub 2019 Jan 9. [PubMed:30634079 ]
Choi SZ, Choi SU, Lee KR: Cytotoxic sesquiterpene lactones from Saussurea calcicola. Arch Pharm Res. 2005 Oct;28(10):1142-6. doi: 10.1007/BF02972976. [PubMed:16276969 ]

Showing NP-Card for Cebellin F (NP0044132)

MOL for NP0044132 (Cebellin F)

3D MOL for NP0044132 (Cebellin F)

3D SDF for NP0044132 (Cebellin F)

3D-SDF for NP0044132 (Cebellin F)

PDB for NP0044132 (Cebellin F)

3D PDB for NP0044132 (Cebellin F)

SMILES for NP0044132 (Cebellin F)

INCHI for NP0044132 (Cebellin F)

Structure for NP0044132 (Cebellin F)

3D Structure for NP0044132 (Cebellin F)