NP-MRD: Showing NP-Card for methyl 10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate (NP0225245)

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Record Information

Version

2.0

Created at

2022-09-06 03:55:04 UTC

Updated at

2022-09-06 03:55:04 UTC

NP-MRD ID

NP0225245

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Sonchifolin 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. Sonchifolin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Sonchifolin has been detected, but not quantified in, green vegetables. methyl 10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate is found in Smallanthus sonchifolius. This could make sonchifolin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061312252D          

 27 28  0  0  0  0            999 V2000
    5.4223   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9374    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9538   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9374   -2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2088   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7239    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2088    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 12  2  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13  3  1  0  0  0  0
 13  6  2  0  0  0  0
 14  4  2  0  0  0  0
 15  9  2  0  0  0  0
 15 11  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22 19  2  0  0  0  0
 23 20  2  0  0  0  0
 24 21  2  0  0  0  0
 25  5  1  0  0  0  0
 25 21  1  0  0  0  0
 26 17  1  0  0  0  0
 26 19  1  0  0  0  0
 27 16  1  0  0  0  0
 27 20  1  0  0  0  0
M  END

     RDKit          3D

 53 54  0  0  0  0  0  0  0  0999 V2000
    1.0227   -2.9840    1.1985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6148   -2.8451   -0.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2807   -3.9932   -0.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5137   -5.2012   -0.6802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486   -3.4679   -2.0672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9166   -2.2194   -1.5639 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9594   -2.6349   -0.6156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9974   -1.9377   -0.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0094   -2.4792    0.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2444   -0.5342   -0.7024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8877    0.4583    0.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1501    1.6280   -0.1066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0420    1.7303   -0.7886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5859    3.1069   -1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4649    3.2846   -1.7511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3113    4.1846   -0.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9632    5.5331   -0.9312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1730    0.6570   -1.3088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2881   -0.3662   -0.2903 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6679    0.0029   -0.0314 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1022    0.4473    1.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2190    0.5227    2.1005 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4819    0.8009    1.4127 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9221    1.2762    2.7408 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3595    0.7076    0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0152    0.2496   -0.8902 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3470   -1.6977   -0.9128 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1291   -4.0029    1.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2735   -2.1888    1.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413   -1.7141   -2.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8749   -3.6525   -0.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9817   -2.6518    0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1783   -1.7365    1.5698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6314   -3.4482    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7255   -0.3446   -1.6297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3533   -0.4353   -0.8716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8634    0.7932    0.8927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996   -0.1028    1.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6688    2.5939    0.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4239    6.2269   -0.2281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3489    5.7835   -1.9511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1488    5.6330   -1.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7737    1.1211   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5840    0.1255   -2.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1967   -0.2568    0.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1647    2.0095    3.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8860    1.8237    2.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417    0.4506    3.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4121    0.9846    0.6404 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2932    0.9590   -1.3690 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6379   -0.8000   -0.9342 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9088    0.2497   -1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0913   -1.6492   -1.7528 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 14  1  0
 14 15  2  0
 14 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 27  1  0
 27 19  1  0
 19 18  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 18 13  1  0
 27  6  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 12 39  1  0
 11 37  1  0
 11 38  1  0
 10 35  1  0
 10 36  1  0
  9 32  1  0
  9 33  1  0
  9 34  1  0
  7 31  1  0
  6 30  1  6
  1 28  1  0
  1 29  1  0
 27 53  1  6
 19 45  1  1
 18 43  1  0
 18 44  1  0
 24 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
M  END


  Mrv0541 05061312252D          

 27 28  0  0  0  0            999 V2000
    5.4223   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9374    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9538   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9374   -2.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2088   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7239    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2088    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 12  2  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13  3  1  0  0  0  0
 13  6  2  0  0  0  0
 14  4  2  0  0  0  0
 15  9  2  0  0  0  0
 15 11  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22 19  2  0  0  0  0
 23 20  2  0  0  0  0
 24 21  2  0  0  0  0
 25  5  1  0  0  0  0
 25 21  1  0  0  0  0
 26 17  1  0  0  0  0
 26 19  1  0  0  0  0
 27 16  1  0  0  0  0
 27 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225245

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C/CC\C(C)=C\C2OC(=O)C(=C)C2C(C\1)OC(=O)C(\C)=C/C

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O6/c1-6-13(3)19(22)26-17-11-15(21(24)25-5)9-7-8-12(2)10-16-18(17)14(4)20(23)27-16/h6,9-10,16-18H,4,7-8,11H2,1-3,5H3/b12-10+,13-6-,15-9+

> <INCHI_KEY>
DBSZDVZLFLCIOQ-VPXSVSNXSA-N

> <FORMULA>
C21H26O6

> <MOLECULAR_WEIGHT>
374.4275

> <EXACT_MASS>
374.172938564

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
38.63998616758588

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.76

> <JCHEM_LOGP>
4.254862069666666

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.17086334895895

> <JCHEM_PKA_STRONGEST_BASIC>
-6.384011163052076

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
101.83319999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.216   0.294   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.121  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.514  -1.941   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.216  -4.326   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.789   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.455   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.789   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.122   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.990  -0.476   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.455  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.085   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.455  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.545   0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      12.789  -3.080   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.122  -3.080   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.788  -2.310   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       5.990   2.016   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5   25                                                            
CONECT    6    1   13                                                       
CONECT    7    8    9                                                       
CONECT    8    7   12                                                       
CONECT    9    7   15                                                       
CONECT   10   12   16                                                       
CONECT   11   15   17                                                       
CONECT   12    2    8   10                                                  
CONECT   13    3    6   19                                                  
CONECT   14    4   18   20                                                  
CONECT   15    9   11   21                                                  
CONECT   16   10   18   27                                                  
CONECT   17   11   18   26                                                  
CONECT   18   14   16   17                                                  
CONECT   19   13   22   26                                                  
CONECT   20   14   23   27                                                  
CONECT   21   15   24   25                                                  
CONECT   22   19                                                            
CONECT   23   20                                                            
CONECT   24   21                                                            
CONECT   25    5   21                                                       
CONECT   26   17   19                                                       
CONECT   27   16   20                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
Methyl 10-methyl-4-{[(2Z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-6-carboxylic acid	Generator

Chemical Formula

C₂₁H₂₆O₆

Average Mass

374.4275 Da

Monoisotopic Mass

374.17294 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C/CC\C(C)=C\C2OC(=O)C(=C)C2C(C\1)OC(=O)C(\C)=C/C

InChI Identifier

InChI=1S/C21H26O6/c1-6-13(3)19(22)26-17-11-15(21(24)25-5)9-7-8-12(2)10-16-18(17)14(4)20(23)27-16/h6,9-10,16-18H,4,7-8,11H2,1-3,5H3/b12-10+,13-6-,15-9+

InChI Key

DBSZDVZLFLCIOQ-VPXSVSNXSA-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
Smallanthus sonchifolius	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
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Methyl ester
Enoate ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
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	2.76	ALOGPS
logP	4.25	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	6.17	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	101.83 m³·mol⁻¹	ChemAxon
Polarizability	38.64 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

HMDB0041139

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021024

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

131753040

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate (NP0225245)

MOL for NP0225245 (methyl 10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D MOL for NP0225245 (methyl 10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D SDF for NP0225245 (methyl 10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D-SDF for NP0225245 (methyl 10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

PDB for NP0225245 (methyl 10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D PDB for NP0225245 (methyl 10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

SMILES for NP0225245 (methyl 10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

INCHI for NP0225245 (methyl 10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

Structure for NP0225245 (methyl 10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)

3D Structure for NP0225245 (methyl 10-methyl-4-{[(2z)-2-methylbut-2-enoyl]oxy}-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-6-carboxylate)