NP-MRD: Showing NP-Card for (2z,4s,9r,11r)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl (2z)-2-methylbut-2-enoate (NP0303276)

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Record Information

Version

2.0

Created at

2022-09-10 17:30:21 UTC

Updated at

2022-09-10 17:30:21 UTC

NP-MRD ID

NP0303276

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z,4s,9r,11r)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl (2z)-2-methylbut-2-enoate

Description

HELIANGOLIDE belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (2z,4s,9r,11r)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl (2z)-2-methylbut-2-enoate is found in Schkuhria pinnata and Tanacetum sinaicum. (2z,4s,9r,11r)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl (2z)-2-methylbut-2-enoate was first documented in 2008 (PMID: 18810997). Based on a literature review a significant number of articles have been published on HELIANGOLIDE (PMID: 35268788) (PMID: 34638856) (PMID: 31955145) (PMID: 23994114) (PMID: 23255452) (PMID: 21674441).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102219302D          

 26 28  0  0  1  0            999 V2000
    5.4278   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6578    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4828    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9034    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    1.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0646   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8492   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3883   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527   -2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376   -2.7560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2322   -2.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473   -1.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8967   -2.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3816   -3.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6041    0.4125    0.0000 O   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
  6  5  1  6  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 17 25  1  0  0  0  0
  2 25  1  0  0  0  0
  6 25  1  0  0  0  0
 14 26  1  0  0  0  0
 10 26  1  0  0  0  0
M  END

     RDKit          3D

 48 50  0  0  0  0  0  0  0  0999 V2000
    0.6877    3.0111   -0.6118 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1886    2.2163    0.3136 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2953    2.4457    1.7502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0732    3.2241    2.3563 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6285    1.6476    2.4228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3043    0.7836    1.4986 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7102    1.1716    1.4211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4917    0.6702    0.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7700    1.3719    0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1380   -0.5254   -0.2824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6542   -0.9957   -1.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6049   -1.7534   -2.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6767   -2.2363   -3.2173 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4972   -1.8098   -1.1123 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9161   -3.2010   -0.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3498   -0.8746   -1.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2206   -0.2387   -0.2130 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6014   -0.0936   -0.2477 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800   -0.7868    0.5759 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8987   -1.5842    1.3886 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9196   -0.6525    0.5521 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7186   -1.4699    1.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5788    0.1461   -0.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8357    0.9736   -1.2294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658    0.9710    0.1710 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1439   -1.4122    0.0880 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5874    2.8057   -1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2318    3.9227   -0.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1364   -0.2439    1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1177    1.8826    2.1526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6158    2.3856   -0.2279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3777    1.4157    1.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3581    0.8062   -0.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6811   -0.8408   -1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1606   -3.3126   -1.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3547   -3.2285   -0.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6793   -3.9817   -0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8084   -0.0373   -2.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -1.4552   -2.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0085   -1.0089    0.5921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2192   -1.5043    2.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7454   -2.5186    1.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7450   -1.0977    1.6233 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6781    0.2127   -0.2371 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5638    1.4577   -1.9454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1677    0.3839   -1.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2952    1.8035   -0.7719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3730    1.1545   -0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 23  1  0
 23 21  2  0
 21 22  1  0
 21 19  1  0
 19 20  2  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 14  1  0
 14 15  1  1
 14 26  1  0
 26 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  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 25  1  0
 25 17  1  0
 12 14  1  0
 25  6  1  0
 24 45  1  0
 24 46  1  0
 24 47  1  0
 23 44  1  0
 22 41  1  0
 22 42  1  0
 22 43  1  0
 17 40  1  1
 16 38  1  0
 16 39  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 11 34  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
 25 48  1  6
M  END


  Mrv1652309102219302D          

 26 28  0  0  1  0            999 V2000
    5.4278   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6578    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4828    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9034    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    1.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0646   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8492   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034   -0.6674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3883   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527   -2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376   -2.7560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2322   -2.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473   -1.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8967   -2.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3816   -3.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6041    0.4125    0.0000 O   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
  6  5  1  6  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  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 17 25  1  0  0  0  0
  2 25  1  0  0  0  0
  6 25  1  0  0  0  0
 14 26  1  0  0  0  0
 10 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303276

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@@H]1C[C@@]2(C)OC(=CC2=O)\C(C)=C/[C@@H]2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O6/c1-6-10(2)18(22)25-15-9-20(5)16(21)8-13(26-20)11(3)7-14-17(15)12(4)19(23)24-14/h6-8,14-15,17H,4,9H2,1-3,5H3/b10-6-,11-7-/t14-,15+,17?,20+/m0/s1

> <INCHI_KEY>
QATUWZPYBIHFFR-VZDUCZRCSA-N

> <FORMULA>
C20H22O6

> <MOLECULAR_WEIGHT>
358.39

> <EXACT_MASS>
358.141638428

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
35.5355132930704

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,4S,9R,11R)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
3.0705717489999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.881129616141192

> <JCHEM_POLAR_SURFACE_AREA>
78.90000000000002

> <JCHEM_REFRACTIVITY>
96.2271

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4S,9R,11R)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      10.132  -1.941   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.656  -0.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.561   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.101   0.770   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.656   2.016   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.191   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.286   2.786   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.822   3.262   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.822   4.802   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.357   2.786   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.452   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.452  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.987  -0.476   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.357  -1.246   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.452  -2.492   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.822  -1.722   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.286  -1.246   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.191  -2.492   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.565  -3.899   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.470  -5.145   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.034  -4.060   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.128  -2.814   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.407  -5.466   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.312  -6.712   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.191  -0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.861   0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   26                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23                                                            
CONECT   25   17    2    6                                                  
CONECT   26   14   10                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₆

Average Mass

358.3900 Da

Monoisotopic Mass

358.14164 Da

IUPAC Name

(2Z,4S,9R,11R)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(2Z,4S,9R,11R)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@@H]1C[C@@]2(C)OC(=CC2=O)\C(C)=C/[C@@H]2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C20H22O6/c1-6-10(2)18(22)25-15-9-20(5)16(21)8-13(26-20)11(3)7-14-17(15)12(4)19(23)24-14/h6-8,14-15,17H,4,9H2,1-3,5H3/b10-6-,11-7-/t14-,15+,17?,20+/m0/s1

InChI Key

QATUWZPYBIHFFR-VZDUCZRCSA-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
Schkuhria pinnata	LOTUS Database	35616633
Tanacetum sinaicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
3-furanone
Gamma butyrolactone
Fatty acyl
Dihydrofuran
Oxolane
Vinylogous ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aldehyde
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	3.07	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	96.23 m³·mol⁻¹	ChemAxon
Polarizability	35.54 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

C00012187

Chemspider ID

28493878

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5384466

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Arakawa NS, Schorr K, Ambrosio SR, Merfort I, Da Costa FB: Further sesquiterpene lactones from Viguiera robusta and the potential anti-inflammatory activity of a heliangolide: inhibition of human neutrophil elastase release. Z Naturforsch C J Biosci. 2008 Jul-Aug;63(7-8):533-8. doi: 10.1515/znc-2008-7-811. [PubMed:18810997 ]
Calzada F, Garcia-Hernandez N, Hidalgo-Figueroa S, Bautista E, Barbosa E, Velazquez C, Hernandez-Caballero ME: Expanding the Study of the Cytotoxicity of Incomptines A and B against Leukemia Cells. Molecules. 2022 Mar 4;27(5):1687. doi: 10.3390/molecules27051687. [PubMed:35268788 ]
Pina-Jimenez E, Calzada F, Bautista E, Ordonez-Razo RM, Velazquez C, Barbosa E, Garcia-Hernandez N: Incomptine A Induces Apoptosis, ROS Production and a Differential Protein Expression on Non-Hodgkin's Lymphoma Cells. Int J Mol Sci. 2021 Sep 29;22(19):10516. doi: 10.3390/ijms221910516. [PubMed:34638856 ]
Onoja SO, Nnadi CO, Udem SC, Anaga AO: Potential antidiabetic and antioxidant activities of a heliangolide sesquiterpene lactone isolated from Helianthus annuus L. leaves. Acta Pharm. 2020 Jun 1;70(2):215-226. doi: 10.2478/acph-2020-0019. [PubMed:31955145 ]
Velazquez-Dominguez J, Marchat LA, Lopez-Camarillo C, Mendoza-Hernandez G, Sanchez-Espindola E, Calzada F, Ortega-Hernandez A, Sanchez-Monroy V, Ramirez-Moreno E: Effect of the sesquiterpene lactone incomptine A in the energy metabolism of Entamoeba histolytica. Exp Parasitol. 2013 Nov;135(3):503-10. doi: 10.1016/j.exppara.2013.08.015. Epub 2013 Aug 28. [PubMed:23994114 ]
Ciric A, Karioti A, Koukoulitsa C, Sokovic M, Skaltsa H: Sesquiterpene lactones from Centaurea zuccariniana and their antimicrobial activity. Chem Biodivers. 2012 Dec;9(12):2843-53. doi: 10.1002/cbdv.201100405. [PubMed:23255452 ]
Kretschmer N, Blunder M, Kunert O, Rechberger GN, Bauer R, Schuehly W: Cytotoxic furanogermacranolides from the flowers of Helianthus angustifolius. Planta Med. 2011 Nov;77(17):1912-5. doi: 10.1055/s-0031-1279994. Epub 2011 Jun 14. [PubMed:21674441 ]
Lakhal H, Boudiar T, Kabouche A, Kabouche Z, Touzani R, Bruneau C: New sesquiterpene lactone and other constituents from Centaurea sulphurea (Asteraceae). Nat Prod Commun. 2010 Jun;5(6):849-50. [PubMed:20614806 ]
Yang NY, Duan JA, Shang EX, Tian LJ: Analysis of sesquiterpene lactones in Eupatorium lindleyanum by HPLC-PDA-ESI-MS/MS. Phytochem Anal. 2010 Mar-Apr;21(2):144-9. doi: 10.1002/pca.1170. [PubMed:19810123 ]
LOTUS database [Link]

Showing NP-Card for (2z,4s,9r,11r)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl (2z)-2-methylbut-2-enoate (NP0303276)

MOL for NP0303276 ((2z,4s,9r,11r)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0303276 ((2z,4s,9r,11r)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0303276 ((2z,4s,9r,11r)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0303276 ((2z,4s,9r,11r)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl (2z)-2-methylbut-2-enoate)

PDB for NP0303276 ((2z,4s,9r,11r)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0303276 ((2z,4s,9r,11r)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0303276 ((2z,4s,9r,11r)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0303276 ((2z,4s,9r,11r)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl (2z)-2-methylbut-2-enoate)

Structure for NP0303276 ((2z,4s,9r,11r)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0303276 ((2z,4s,9r,11r)-2,11-dimethyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl (2z)-2-methylbut-2-enoate)