NP-MRD: Showing NP-Card for 10-methyl-4-{[(2e)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylic acid (NP0184915)

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Record Information

Version

1.0

Created at

2022-09-04 00:10:14 UTC

Updated at

2022-09-04 00:10:14 UTC

NP-MRD ID

NP0184915

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-methyl-4-{[(2e)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylic acid

Description

Germanin B belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. 10-methyl-4-{[(2e)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylic acid is found in Inula germanica. It was first documented in 2020 (PMID: 33519460). Based on a literature review a significant number of articles have been published on Germanin B (PMID: 33493498) (PMID: 35693834) (PMID: 35671324) (PMID: 35356785) (PMID: 35269985) (PMID: 35250636).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042202102D          

 26 27  0  0  0  0            999 V2000
    2.8558   -0.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279    1.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    0.9838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460    2.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701    2.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929    2.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070    2.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0298    3.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983    1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124    1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037    0.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6722   -0.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1494   -1.1117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4863   -0.6072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755    1.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7527    0.5656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8581   -0.3399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212   -0.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7071   -0.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125   -1.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2897   -2.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614    1.3375    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 18 26  1  0  0  0  0
  2 26  1  0  0  0  0
  6 26  1  0  0  0  0
M  END

     RDKit          3D

 50 51  0  0  0  0  0  0  0  0999 V2000
   -1.3353   -2.5865    1.5113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4240   -1.8558    0.4466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4407   -2.2086   -0.9894 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0762   -3.3161   -1.4393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9263   -1.1066   -1.7360 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5195   -0.2957   -0.7457 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2373    0.8714   -1.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8337    1.7860   -1.9091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6925    3.0059   -2.1914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5830    1.6828   -2.6041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767    2.9379   -2.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6291    2.6108   -1.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0672    2.0010   -0.8861 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5291    1.7887   -0.7851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9763    1.2298    0.2214 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3831    2.1996   -1.7802 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1411    1.5609    0.2132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1550    0.1100    0.1354 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6249   -0.5541    1.1582 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5303   -1.5326    0.8633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7091   -1.8751   -0.3290 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2676   -2.1489    1.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2960   -3.2109    1.6664 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1049   -1.8309    3.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9052   -2.4946    4.3150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5490   -0.3274    0.3974 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3400   -2.1214    2.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2520   -3.6510    1.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3271   -1.0517   -0.3565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2364    1.0407   -0.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4332    3.4554   -3.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5658    3.7652   -1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7763    2.6999   -2.1516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9583    0.8238   -2.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8078    1.7968   -3.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2499    3.4820   -1.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8242    3.7004   -3.0751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714    2.8939   -2.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2977    2.6062   -1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7893    2.1375    0.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6979    1.8216    1.1597 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1621   -0.3573   -0.8384 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1202   -3.0725    2.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8855   -4.2253    1.8301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6928   -3.0554    0.6304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3867   -1.0794    3.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3801   -2.4016    5.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0168   -3.5817    4.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9209   -2.0450    4.3526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9866   -0.0219    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
 25 24  1  0
 24 22  2  0
 22 23  1  0
 22 20  1  0
 20 21  2  0
 20 19  1  0
 19 18  1  0
 18 17  1  0
 17 13  1  0
 13 12  2  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 26  1  0
 13 14  1  0
 14 16  1  0
 14 15  2  0
 26 18  1  0
 26  6  1  0
 25 47  1  0
 25 48  1  0
 25 49  1  0
 24 46  1  0
 23 43  1  0
 23 44  1  0
 23 45  1  0
 18 42  1  6
 17 40  1  0
 17 41  1  0
 12 38  1  0
 11 36  1  0
 11 37  1  0
 10 34  1  0
 10 35  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
  7 30  1  0
  6 29  1  1
  1 27  1  0
  1 28  1  0
 26 50  1  1
 16 39  1  0
M  END


  Mrv1652309042202102D          

 26 27  0  0  0  0            999 V2000
    2.8558   -0.0022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279    1.2751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    0.9838    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3460    2.0708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701    2.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6929    2.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5070    2.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0298    3.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7983    1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6124    1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9037    0.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3809    0.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6722   -0.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1494   -1.1117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4863   -0.6072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5668    0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2755    1.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7527    0.5656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0440   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8581   -0.3399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212   -0.8444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7071   -0.7108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125   -1.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2897   -2.2545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4614    1.3375    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 18 26  1  0  0  0  0
  2 26  1  0  0  0  0
  6 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184915

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)OC1C\C(=C/CC\C(C)=C/C2OC(=O)C(=C)C12)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O6/c1-5-12(3)19(23)25-16-10-14(18(21)22)8-6-7-11(2)9-15-17(16)13(4)20(24)26-15/h5,8-9,15-17H,4,6-7,10H2,1-3H3,(H,21,22)/b11-9-,12-5+,14-8+

> <INCHI_KEY>
IOPBGRHISQTQKP-KODVERRDSA-N

> <FORMULA>
C20H24O6

> <MOLECULAR_WEIGHT>
360.406

> <EXACT_MASS>
360.157288493

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
37.18872953347968

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-methyl-4-{[(2E)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylic acid

> <JCHEM_LOGP>
3.8756346803333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.470153883354631

> <JCHEM_PKA_STRONGEST_BASIC>
-6.565297752457939

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
97.0641

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
10-methyl-4-{[(2E)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       5.331  -0.004   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.259   1.534   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.972   2.380   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.531   1.836   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.379   3.866   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.917   3.937   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.893   5.129   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.413   4.879   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.389   6.071   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.957   3.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.476   3.189   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.020   1.748   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.044   0.557   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.588  -0.884   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.612  -2.075   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      12.108  -1.133   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.525   0.806   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.981   2.247   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.005   1.056   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.549  -0.385   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.068  -0.634   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.573  -1.576   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.053  -1.327   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.117  -3.017   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.141  -4.208   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.461   2.497   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   26                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   17                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   18    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₆

Average Mass

360.4060 Da

Monoisotopic Mass

360.15729 Da

IUPAC Name

10-methyl-4-{[(2E)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylic acid

Traditional Name

10-methyl-4-{[(2E)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylic acid

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)OC1C\C(=C/CC\C(C)=C/C2OC(=O)C(=C)C12)C(O)=O

InChI Identifier

InChI=1S/C20H24O6/c1-5-12(3)19(23)25-16-10-14(18(21)22)8-6-7-11(2)9-15-17(16)13(4)20(24)26-15/h5,8-9,15-17H,4,6-7,10H2,1-3H3,(H,21,22)/b11-9-,12-5+,14-8+

InChI Key

IOPBGRHISQTQKP-KODVERRDSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Inula germanica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Oxolane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	3.88	ChemAxon
pKa (Strongest Acidic)	4.47	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.06 m³·mol⁻¹	ChemAxon
Polarizability	37.19 Å³	ChemAxon
Number of Rings	2	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

113642498

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

90473376

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chama MA, Modos D, Mervin LH, Owusu KB, Ayine-Tora DM, Egyir B, Paemka L, Yankson G, Ohashi M, Afzal AM, Bender A: Towards understanding antimicrobial activity, cytotoxicity and the mode of action of dichapetalins A and M using in silico and in vitro studies. Toxicon. 2021 Apr 15;193:28-37. doi: 10.1016/j.toxicon.2021.01.002. Epub 2021 Jan 23. [PubMed:33493498 ]
Zhang M, Fei S, Xia J, Wang Y, Wu H, Li X, Guo Y, Swevers L, Sun J, Feng M: Sirt5 Inhibits BmNPV Replication by Promoting a Relish-Mediated Antiviral Pathway in Bombyx mori. Front Immunol. 2022 May 23;13:906738. doi: 10.3389/fimmu.2022.906738. eCollection 2022. [PubMed:35693834 ]
Marriott AE, Furlong Silva J, Pionnier N, Sjoberg H, Archer J, Steven A, Kempf D, Taylor MJ, Turner JD: A mouse infection model and long-term lymphatic endothelium co-culture system to evaluate drugs against adult Brugia malayi. PLoS Negl Trop Dis. 2022 Jun 7;16(6):e0010474. doi: 10.1371/journal.pntd.0010474. eCollection 2022 Jun. [PubMed:35671324 ]
Kasozi KI, MacLeod ET, Ntulume I, Welburn SC: An Update on African Trypanocide Pharmaceutics and Resistance. Front Vet Sci. 2022 Mar 7;9:828111. doi: 10.3389/fvets.2022.828111. eCollection 2022. [PubMed:35356785 ]
Ungogo MA, Campagnaro GD, Alghamdi AH, Natto MJ, de Koning HP: Differences in Transporters Rather than Drug Targets Are the Principal Determinants of the Different Innate Sensitivities of Trypanosoma congolense and Trypanozoon Subgenus Trypanosomes to Diamidines and Melaminophenyl Arsenicals. Int J Mol Sci. 2022 Mar 5;23(5):2844. doi: 10.3390/ijms23052844. [PubMed:35269985 ]
Domnik NJ, Vincent SG, Fisher JT: Mechanosensitivity of Murine Lung Slowly Adapting Receptors: Minimal Impact of Chemosensory, Serotonergic, and Purinergic Signaling. Front Physiol. 2022 Feb 16;13:833665. doi: 10.3389/fphys.2022.833665. eCollection 2022. [PubMed:35250636 ]
Ullah A, Khan A, Al-Harrasi A, Ullah K, Shabbir A: Three-Dimensional Structure Characterization and Inhibition Study of Exfoliative Toxin D From Staphylococcus aureus. Front Pharmacol. 2022 Feb 18;13:800970. doi: 10.3389/fphar.2022.800970. eCollection 2022. [PubMed:35250557 ]
Gangwar M, Jha R, Goyal M, Srivastava M: Biochemical characterization of Recombinase A from Wolbachia endosymbiont of filarial nematode Brugia malayi (wBmRecA). Int J Parasitol. 2021 Sep;51(10):841-853. doi: 10.1016/j.ijpara.2021.02.007. Epub 2021 Jul 15. [PubMed:34273392 ]
Ullah A, Ullah K: Inhibition of SARS-CoV-2 3CL M(pro) by Natural and Synthetic Inhibitors: Potential Implication for Vaccine Production Against COVID-19. Front Mol Biosci. 2021 Apr 12;8:640819. doi: 10.3389/fmolb.2021.640819. eCollection 2021. [PubMed:33912587 ]
Bojadzic D, Alcazar O, Buchwald P: Methylene Blue Inhibits the SARS-CoV-2 Spike-ACE2 Protein-Protein Interaction-a Mechanism that can Contribute to its Antiviral Activity Against COVID-19. Front Pharmacol. 2021 Jan 13;11:600372. doi: 10.3389/fphar.2020.600372. eCollection 2020. [PubMed:33519460 ]
Feng CW, Chen NF, Chan TF, Chen WF: Therapeutic Role of Protein Tyrosine Phosphatase 1B in Parkinson's Disease via Antineuroinflammation and Neuroprotection In Vitro and In Vivo. Parkinsons Dis. 2020 Dec 29;2020:8814236. doi: 10.1155/2020/8814236. eCollection 2020. [PubMed:33456749 ]
Kwiatkowski MA, Roberts BZ, van Enkhuizen J, Ji B, Zhou X, Young JW: Chronic nicotine, but not suramin or resveratrol, partially remediates the mania-like profile of dopamine transporter knockdown mice. Eur Neuropsychopharmacol. 2021 Jan;42:75-86. doi: 10.1016/j.euroneuro.2020.11.004. Epub 2020 Nov 13. [PubMed:33191077 ]
Ndung'u K, Murilla GA, Thuita JK, Ngae GN, Auma JE, Gitonga PK, Thungu DK, Kurgat RK, Chemuliti JK, Mdachi RE: Differential virulence of Trypanosoma brucei rhodesiense isolates does not influence the outcome of treatment with anti-trypanosomal drugs in the mouse model. PLoS One. 2020 Nov 5;15(11):e0229060. doi: 10.1371/journal.pone.0229060. eCollection 2020. [PubMed:33151938 ]
Zhu W, Xu M, Chen CZ, Guo H, Shen M, Hu X, Shinn P, Klumpp-Thomas C, Michael SG, Zheng W: Identification of SARS-CoV-2 3CL Protease Inhibitors by a Quantitative High-Throughput Screening. ACS Pharmacol Transl Sci. 2020 Sep 4;3(5):1008-1016. doi: 10.1021/acsptsci.0c00108. eCollection 2020 Oct 9. [PubMed:33062953 ]
Zhu W, Xu M, Chen CZ, Guo H, Shen M, Hu X, Shinn P, Klumpp-Thomas C, Michael SG, Zheng W: Identification of SARS-CoV-2 3CL Protease Inhibitors by a Quantitative High-throughput Screening. bioRxiv. 2020 Aug 11:2020.07.17.207019. doi: 10.1101/2020.07.17.207019. Preprint. [PubMed:32803196 ]
LOTUS database [Link]

Showing NP-Card for 10-methyl-4-{[(2e)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylic acid (NP0184915)

MOL for NP0184915 (10-methyl-4-{[(2e)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylic acid)

3D MOL for NP0184915 (10-methyl-4-{[(2e)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylic acid)

3D SDF for NP0184915 (10-methyl-4-{[(2e)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylic acid)

3D-SDF for NP0184915 (10-methyl-4-{[(2e)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylic acid)

PDB for NP0184915 (10-methyl-4-{[(2e)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylic acid)

3D PDB for NP0184915 (10-methyl-4-{[(2e)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylic acid)

SMILES for NP0184915 (10-methyl-4-{[(2e)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylic acid)

INCHI for NP0184915 (10-methyl-4-{[(2e)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylic acid)

Structure for NP0184915 (10-methyl-4-{[(2e)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylic acid)

3D Structure for NP0184915 (10-methyl-4-{[(2e)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylic acid)