NP-MRD: Showing NP-Card for 9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate (NP0258596)

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Record Information

Version

2.0

Created at

2022-09-08 00:07:57 UTC

Updated at

2022-09-08 00:07:57 UTC

NP-MRD ID

NP0258596

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate

Description

9-Hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]Tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate 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. 9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate is found in Eremanthus glomerulatus. 9-Hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]Tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191513312D          

 28 31  0  0  0  0            999 V2000
    4.2307    4.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8353    4.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6396    4.2039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0783    3.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3891    2.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4665    3.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6813    3.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6398    2.2393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280    1.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    2.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4823    2.9041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4923    2.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1550    2.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8804    1.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7107    0.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0480   -0.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4361   -0.6584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7633   -0.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5936   -1.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5836   -0.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1955    0.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9109   -0.2853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5227    0.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3301    0.0984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1855    1.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5964    1.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3652    0.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5683    0.5801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  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
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 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
  9 27  1  0  0  0  0
 21 27  1  0  0  0  0
 18 28  1  0  0  0  0
 14 28  1  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
   -0.3719    2.6222   -1.6689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6242    2.4196   -0.4109 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4336    3.4059    0.3546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    4.5265   -0.0582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6356    2.8720    1.6434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6140    1.4487    1.3856 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8400    1.1757    0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6992    0.0744    1.1477 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5025    0.4530    2.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8703   -1.0559    1.3410 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5435   -1.4447    0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6544   -1.3486   -0.7014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5466   -0.4199    0.0027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7219   -0.1149   -0.2799 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1884   -1.8546   -0.3047 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1181   -3.0353   -1.2459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3257   -0.6962   -0.8320 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7736   -1.3820   -1.4206 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370    0.1336    0.2562 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6668    0.2729    0.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5793   -0.2569    0.9893 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1914   -0.9357    1.9609 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0256   -0.0599    0.7977 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3800    0.7875   -0.4241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8506    0.0465    1.9156 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9890   -1.1553    1.0610 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2988   -1.1773    0.3099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3241    1.4238    0.5841 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6967    3.4566   -2.2561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2303    1.8862   -2.2058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5376    0.8853    2.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5096    2.0523    0.4547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5430    0.8781   -0.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9167    1.1403    2.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8111   -0.4654    2.8649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4361    0.9491    1.9893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8775   -1.8515   -1.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6705   -2.1773    0.6424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2644   -2.7584   -2.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1051   -3.5064   -1.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8647   -3.7720   -0.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8074   -0.1951   -1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2226   -1.9314   -0.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469   -0.5068    1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1309    0.2136   -1.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4464    1.0863   -0.4094 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6854    1.6477   -0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7111   -2.0588    1.6222 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7355   -2.2162    0.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1456   -0.8818   -0.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0639   -0.5213    0.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148    1.9216    1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  1  0
 26 25  1  0
 25 23  1  0
 23 24  1  0
 23 21  1  1
 21 22  2  0
 21 20  1  0
 20 19  1  0
 19 28  1  0
 28  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 11 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
 23 26  1  0
 17 19  1  0
  2 28  1  0
 13  8  1  0
 27 49  1  0
 27 50  1  0
 27 51  1  0
 26 48  1  1
 24 45  1  0
 24 46  1  0
 24 47  1  0
 19 44  1  1
 28 52  1  1
  6 31  1  1
  7 32  1  0
  7 33  1  0
  9 34  1  0
  9 35  1  0
  9 36  1  0
 12 37  1  0
 15 38  1  1
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  6
 18 43  1  0
  1 29  1  0
  1 30  1  0
M  END


  Mrv1533004191513312D          

 28 31  0  0  0  0            999 V2000
    4.2307    4.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8353    4.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6396    4.2039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0783    3.5993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3891    2.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4665    3.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6813    3.2991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6398    2.2393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280    1.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    2.0968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4823    2.9041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4923    2.0087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1550    2.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8804    1.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7107    0.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0480   -0.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4361   -0.6584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7633   -0.5159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5936   -1.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5836   -0.4278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1955    0.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9109   -0.2853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5227    0.2681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3301    0.0984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1855    1.0211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5964    1.7364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3652    0.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5683    0.5801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  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
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 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
  9 27  1  0  0  0  0
 21 27  1  0  0  0  0
 18 28  1  0  0  0  0
 14 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0258596

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC1(C)C(=O)OC1C2C(CC3(C)OC(=CC3=O)C(C)C1O)OC(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O8/c1-8-11-6-13(21)19(4,28-11)7-12-14(9(2)17(23)25-12)16(15(8)22)26-18(24)20(5)10(3)27-20/h6,8,10,12,14-16,22H,2,7H2,1,3-5H3

> <INCHI_KEY>
DPWFMICLQOCEEX-UHFFFAOYSA-N

> <FORMULA>
C20H24O8

> <MOLECULAR_WEIGHT>
392.404

> <EXACT_MASS>
392.147117733

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.11876154051426

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
1.1527820486666673

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.15517864288448

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.751718133177334

> <JCHEM_PKA_STRONGEST_BASIC>
-3.336225522197606

> <JCHEM_POLAR_SURFACE_AREA>
111.66000000000001

> <JCHEM_REFRACTIVITY>
95.5543

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.62e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       7.897   9.238   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.026   8.190   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      10.527   7.847   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       9.480   6.719   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.060   5.292   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.337   5.686   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.872   6.158   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       8.661   4.180   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.519   3.147   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.183   3.914   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.500   5.421   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.652   3.750   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.023   5.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.510   2.717   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.193   1.210   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.823  -0.196   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.681  -1.229   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.158  -0.963   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.841  -2.470   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.689  -0.799   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.832   0.234   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.167  -0.533   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      10.309   0.501   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.816   0.184   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.680   1.906   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.447   3.241   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.148   1.742   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.794   1.083   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2    4                                                       
CONECT    4    3    2    5    6                                             
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   27                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   28                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20   28                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    9   21                                                  
CONECT   28   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
9-Hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0,]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylic acid	Generator
9-Hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylic acid	Generator

Chemical Formula

C₂₀H₂₄O₈

Average Mass

392.4040 Da

Monoisotopic Mass

392.14712 Da

IUPAC Name

9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate

Traditional Name

9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate

CAS Registry Number

Not Available

SMILES

CC1OC1(C)C(=O)OC1C2C(CC3(C)OC(=CC3=O)C(C)C1O)OC(=O)C2=C

InChI Identifier

InChI=1S/C20H24O8/c1-8-11-6-13(21)19(4,28-11)7-12-14(9(2)17(23)25-12)16(15(8)22)26-18(24)20(5)10(3)27-20/h6,8,10,12,14-16,22H,2,7H2,1,3-5H3

InChI Key

DPWFMICLQOCEEX-UHFFFAOYSA-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
Eremanthus glomerulatus	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
Sesquiterpenoid
Dicarboxylic acid or derivatives
3-furanone
Gamma butyrolactone
Oxirane carboxylic acid
Oxirane carboxylic acid or derivatives
Dihydrofuran
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Enoate ester
Carboxylic acid ester
Secondary alcohol
Lactone
Ketone
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organic oxygen compound
Alcohol
Organooxygen compound
Organic oxide
Hydrocarbon derivative
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	1.03	ALOGPS
logP	1.15	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	13.75	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.66 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.55 m³·mol⁻¹	ChemAxon
Polarizability	39.12 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate (NP0258596)

MOL for NP0258596 (9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate)

3D MOL for NP0258596 (9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate)

3D SDF for NP0258596 (9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate)

3D-SDF for NP0258596 (9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate)

PDB for NP0258596 (9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate)

3D PDB for NP0258596 (9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate)

SMILES for NP0258596 (9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate)

INCHI for NP0258596 (9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate)

Structure for NP0258596 (9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate)

3D Structure for NP0258596 (9-hydroxy-1,10-dimethyl-6-methylidene-5,13-dioxo-4,14-dioxatricyclo[9.2.1.0³,⁷]tetradec-11-en-8-yl 2,3-dimethyloxirane-2-carboxylate)