NP-MRD: Showing NP-Card for parthenolide (NP0028992)

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Record Information

Version

2.0

Created at

2021-06-19 20:43:50 UTC

Updated at

2021-06-29 23:56:05 UTC

NP-MRD ID

NP0028992

Secondary Accession Numbers

None

Natural Product Identification

Common Name

parthenolide

Provided By

JEOL Database JEOL Logo

Description

parthenolide is found in Ambrosia spp., Anthemis cretica subsp.tenuiloba, Anthemis macedonica, Anthemis melampodina, Anthemis stribrnyi subsp. tracica, Arctotis arctotoides, Arctotis spp., Carpesium longifolium, Cyathocline purpurea, Eriocephalus kingesii, Magnolia denudata, Magnolia grandiflora , Magnolia nilagirica, Magnolia praecocissima , Magnolia salicifolia, Magnolia virginiana , Magnolia baillonii, Michelia champaca , Magnolia compressa, Michelia lanuginosa, Michelia yunnanensis, Pentanema aschersonianum, Staehelina fruticosa, Tanacetum argenteum, Tanacetum densum, Tanacetum parthenium , Tanacetum vulgare, Tarchonanthus camphoratus and Tripterygium wilfordii . parthenolide was first documented in 2002 (Wong, H.-F., et al.). Based on a literature review very few articles have been published on parthenolide.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122433D          

 38 40  0  0  0  0            999 V2000
   -7.0530   -0.5639   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0648    0.0820   -0.8534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2960    0.8037   -2.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2904    0.7368   -2.8239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1857    1.5401   -2.3874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3291    1.5588   -1.2337 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6280    0.2596   -0.4805 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3450    0.2791    1.0314 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8974    0.5549    1.4758 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8182   -0.3047    0.8510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0306   -1.7968    0.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6893    0.1761    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2053    1.6054    0.2211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5027    2.3089   -1.1106 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9514    2.7083   -1.2131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3761    3.9260   -0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5135    2.7169   -2.5338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078    1.6242   -1.6920 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8934   -1.0923    0.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0581   -0.5881   -0.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6082    2.4347   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0829   -0.5751   -0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9889    1.0287    1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6497   -0.6856    1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482    0.4103    2.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6969    1.6156    1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2076   -2.0872    1.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1608   -2.3616    0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891   -2.1116    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0174   -0.5374   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886    2.1878    1.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836    1.5792    0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1207    3.2081   -1.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2131    1.6630   -1.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3599    4.2920   -0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4153    3.7233    0.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659    4.7440   -0.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5256    0.6597   -2.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
 15 18  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 13 12  1  0  0  0  0
  6  5  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
  2  7  1  0  0  0  0
 14 15  1  0  0  0  0
 10 11  1  0  0  0  0
 10  9  1  0  0  0  0
  3  4  2  0  0  0  0
 18  6  1  0  0  0  0
  2  1  2  3  0  0  0
  7  8  1  0  0  0  0
 18 17  1  0  0  0  0
 15 17  1  0  0  0  0
  8  9  1  0  0  0  0
 15 16  1  1  0  0  0
 13 31  1  0  0  0  0
 13 32  1  0  0  0  0
 14 33  1  0  0  0  0
 14 34  1  0  0  0  0
 12 30  1  0  0  0  0
 18 38  1  6  0  0  0
  8 23  1  0  0  0  0
  8 24  1  0  0  0  0
  9 25  1  0  0  0  0
  9 26  1  0  0  0  0
  7 22  1  6  0  0  0
  6 21  1  1  0  0  0
 11 27  1  0  0  0  0
 11 28  1  0  0  0  0
 11 29  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
 16 37  1  0  0  0  0
M  END

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -7.0530   -0.5639   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0648    0.0820   -0.8534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2960    0.8037   -2.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2904    0.7368   -2.8239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1857    1.5401   -2.3874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3291    1.5588   -1.2337 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6280    0.2596   -0.4805 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3450    0.2791    1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8974    0.5549    1.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8182   -0.3047    0.8510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0306   -1.7968    0.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6893    0.1761    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2053    1.6054    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5027    2.3089   -1.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9514    2.7083   -1.2131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3761    3.9260   -0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5135    2.7169   -2.5338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078    1.6242   -1.6920 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8934   -1.0923    0.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0581   -0.5881   -0.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6082    2.4347   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0829   -0.5751   -0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9889    1.0287    1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6497   -0.6856    1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482    0.4103    2.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6969    1.6156    1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2076   -2.0872    1.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1608   -2.3616    0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891   -2.1116    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0174   -0.5374   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886    2.1878    1.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836    1.5792    0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1207    3.2081   -1.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2131    1.6630   -1.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3599    4.2920   -0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4153    3.7233    0.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659    4.7440   -0.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5256    0.6597   -2.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
 15 18  1  0
 10 12  2  0
 13 14  1  0
 13 12  1  0
  6  5  1  0
  5  3  1  0
  3  2  1  0
  2  7  1  0
 14 15  1  0
 10 11  1  0
 10  9  1  0
  3  4  2  0
 18  6  1  0
  2  1  2  3
  7  8  1  0
 18 17  1  0
 15 17  1  0
  8  9  1  0
 15 16  1  1
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 12 30  1  0
 18 38  1  6
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  7 22  1  6
  6 21  1  1
 11 27  1  0
 11 28  1  0
 11 29  1  0
  1 19  1  0
  1 20  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
M  END


  Mrv1652306192122433D          

 38 40  0  0  0  0            999 V2000
   -7.0530   -0.5639   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0648    0.0820   -0.8534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2960    0.8037   -2.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2904    0.7368   -2.8239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1857    1.5401   -2.3874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3291    1.5588   -1.2337 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6280    0.2596   -0.4805 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3450    0.2791    1.0314 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8974    0.5549    1.4758 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8182   -0.3047    0.8510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0306   -1.7968    0.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6893    0.1761    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2053    1.6054    0.2211 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5027    2.3089   -1.1106 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9514    2.7083   -1.2131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3761    3.9260   -0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5135    2.7169   -2.5338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078    1.6242   -1.6920 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8934   -1.0923    0.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0581   -0.5881   -0.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6082    2.4347   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0829   -0.5751   -0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9889    1.0287    1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6497   -0.6856    1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482    0.4103    2.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6969    1.6156    1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2076   -2.0872    1.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1608   -2.3616    0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891   -2.1116    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0174   -0.5374   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886    2.1878    1.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836    1.5792    0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1207    3.2081   -1.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2131    1.6630   -1.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3599    4.2920   -0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4153    3.7233    0.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659    4.7440   -0.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5256    0.6597   -2.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
 15 18  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 13 12  1  0  0  0  0
  6  5  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
  2  7  1  0  0  0  0
 14 15  1  0  0  0  0
 10 11  1  0  0  0  0
 10  9  1  0  0  0  0
  3  4  2  0  0  0  0
 18  6  1  0  0  0  0
  2  1  2  3  0  0  0
  7  8  1  0  0  0  0
 18 17  1  0  0  0  0
 15 17  1  0  0  0  0
  8  9  1  0  0  0  0
 15 16  1  1  0  0  0
 13 31  1  0  0  0  0
 13 32  1  0  0  0  0
 14 33  1  0  0  0  0
 14 34  1  0  0  0  0
 12 30  1  0  0  0  0
 18 38  1  6  0  0  0
  8 23  1  0  0  0  0
  8 24  1  0  0  0  0
  9 25  1  0  0  0  0
  9 26  1  0  0  0  0
  7 22  1  6  0  0  0
  6 21  1  1  0  0  0
 11 27  1  0  0  0  0
 11 28  1  0  0  0  0
 11 29  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 16 35  1  0  0  0  0
 16 36  1  0  0  0  0
 16 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0028992

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C1C(=O)O[C@]2([H])[C@@]3([H])O[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])\C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])[C@@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5-/t11-,12-,13+,15+/m0/s1

> <INCHI_KEY>
KTEXNACQROZXEV-ZRPLFPEYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
27.098874585214183

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4R,7Z,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0^{2,4}]tetradec-7-en-13-one

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
3.071292598333333

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2427719335752

> <JCHEM_POLAR_SURFACE_AREA>
38.83

> <JCHEM_REFRACTIVITY>
68.5529

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4R,7Z,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0^{2,4}]tetradec-7-en-13-one

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -7.0530   -0.5639   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0648    0.0820   -0.8534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2960    0.8037   -2.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2904    0.7368   -2.8239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1857    1.5401   -2.3874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3291    1.5588   -1.2337 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6280    0.2596   -0.4805 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3450    0.2791    1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8974    0.5549    1.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8182   -0.3047    0.8510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0306   -1.7968    0.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6893    0.1761    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2053    1.6054    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5027    2.3089   -1.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9514    2.7083   -1.2131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3761    3.9260   -0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5135    2.7169   -2.5338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078    1.6242   -1.6920 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8934   -1.0923    0.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0581   -0.5881   -0.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6082    2.4347   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0829   -0.5751   -0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9889    1.0287    1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6497   -0.6856    1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482    0.4103    2.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6969    1.6156    1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2076   -2.0872    1.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1608   -2.3616    0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891   -2.1116    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0174   -0.5374   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886    2.1878    1.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836    1.5792    0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1207    3.2081   -1.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2131    1.6630   -1.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3599    4.2920   -0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4153    3.7233    0.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659    4.7440   -0.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5256    0.6597   -2.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
 15 18  1  0
 10 12  2  0
 13 14  1  0
 13 12  1  0
  6  5  1  0
  5  3  1  0
  3  2  1  0
  2  7  1  0
 14 15  1  0
 10 11  1  0
 10  9  1  0
  3  4  2  0
 18  6  1  0
  2  1  2  3
  7  8  1  0
 18 17  1  0
 15 17  1  0
  8  9  1  0
 15 16  1  1
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 12 30  1  0
 18 38  1  6
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  7 22  1  6
  6 21  1  1
 11 27  1  0
 11 28  1  0
 11 29  1  0
  1 19  1  0
  1 20  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -7.053  -0.564  -0.222  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.065   0.082  -0.853  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.296   0.804  -2.127  0.00  0.00           C+0
HETATM    4  O   UNK     0      -7.290   0.737  -2.824  0.00  0.00           O+0
HETATM    5  O   UNK     0      -5.186   1.540  -2.387  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.329   1.559  -1.234  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.628   0.260  -0.481  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.345   0.279   1.031  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.897   0.555   1.476  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.818  -0.305   0.851  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.031  -1.797   0.944  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.689   0.176   0.287  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.205   1.605   0.221  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.503   2.309  -1.111  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.951   2.708  -1.213  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.376   3.926  -0.442  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.514   2.717  -2.534  0.00  0.00           O+0
HETATM   18  C   UNK     0      -2.908   1.624  -1.692  0.00  0.00           C+0
HETATM   19  H   UNK     0      -6.893  -1.092   0.711  0.00  0.00           H+0
HETATM   20  H   UNK     0      -8.058  -0.588  -0.638  0.00  0.00           H+0
HETATM   21  H   UNK     0      -4.608   2.435  -0.637  0.00  0.00           H+0
HETATM   22  H   UNK     0      -4.083  -0.575  -0.940  0.00  0.00           H+0
HETATM   23  H   UNK     0      -4.989   1.029   1.512  0.00  0.00           H+0
HETATM   24  H   UNK     0      -4.650  -0.686   1.459  0.00  0.00           H+0
HETATM   25  H   UNK     0      -2.848   0.410   2.563  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.697   1.616   1.321  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.208  -2.087   1.985  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.161  -2.362   0.592  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.889  -2.112   0.345  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.017  -0.537  -0.140  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.589   2.188   1.066  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.884   1.579   0.359  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.121   3.208  -1.186  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.213   1.663  -1.950  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.360   4.292  -0.754  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.415   3.723   0.631  0.00  0.00           H+0
HETATM   37  H   UNK     0      -1.666   4.744  -0.604  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.526   0.660  -2.004  0.00  0.00           H+0
CONECT    1    2   19   20                                                  
CONECT    2    3    7    1                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    6    3                                                       
CONECT    6    7    5   18   21                                             
CONECT    7    6    2    8   22                                             
CONECT    8    7    9   23   24                                             
CONECT    9   10    8   25   26                                             
CONECT   10   12   11    9                                                  
CONECT   11   10   27   28   29                                             
CONECT   12   10   13   30                                                  
CONECT   13   14   12   31   32                                             
CONECT   14   13   15   33   34                                             
CONECT   15   18   14   17   16                                             
CONECT   16   15   35   36   37                                             
CONECT   17   18   15                                                       
CONECT   18   15    6   17   38                                             
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    6                                                            
CONECT   22    7                                                            
CONECT   23    8                                                            
CONECT   24    8                                                            
CONECT   25    9                                                            
CONECT   26    9                                                            
CONECT   27   11                                                            
CONECT   28   11                                                            
CONECT   29   11                                                            
CONECT   30   12                                                            
CONECT   31   13                                                            
CONECT   32   13                                                            
CONECT   33   14                                                            
CONECT   34   14                                                            
CONECT   35   16                                                            
CONECT   36   16                                                            
CONECT   37   16                                                            
CONECT   38   18                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

RDKit          3D

38 40  0  0  0  0  0  0  0  0999 V2000
   -7.0530   -0.5639   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0648    0.0820   -0.8534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2960    0.8037   -2.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2904    0.7368   -2.8239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1857    1.5401   -2.3874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3291    1.5588   -1.2337 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6280    0.2596   -0.4805 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3450    0.2791    1.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8974    0.5549    1.4758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8182   -0.3047    0.8510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0306   -1.7968    0.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6893    0.1761    0.2865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2053    1.6054    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5027    2.3089   -1.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9514    2.7083   -1.2131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3761    3.9260   -0.4424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5135    2.7169   -2.5338 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078    1.6242   -1.6920 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8934   -1.0923    0.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0581   -0.5881   -0.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6082    2.4347   -0.6373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0829   -0.5751   -0.9396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9889    1.0287    1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6497   -0.6856    1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482    0.4103    2.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6969    1.6156    1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2076   -2.0872    1.9849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1608   -2.3616    0.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8891   -2.1116    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0174   -0.5374   -0.1404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5886    2.1878    1.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836    1.5792    0.3592 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1207    3.2081   -1.1863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2131    1.6630   -1.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3599    4.2920   -0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4153    3.7233    0.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659    4.7440   -0.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5256    0.6597   -2.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
 15 18  1  0
 10 12  2  0
 13 14  1  0
 13 12  1  0
  6  5  1  0
  5  3  1  0
  3  2  1  0
  2  7  1  0
 14 15  1  0
 10 11  1  0
 10  9  1  0
  3  4  2  0
 18  6  1  0
  2  1  2  3
  7  8  1  0
 18 17  1  0
 15 17  1  0
  8  9  1  0
 15 16  1  1
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 12 30  1  0
 18 38  1  6
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  7 22  1  6
  6 21  1  1
 11 27  1  0
 11 28  1  0
 11 29  1  0
  1 19  1  0
  1 20  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
M  END

View in JSmol

Synonyms

Value	Source
Parthenolide, (1ar-(1ar,4E,7as,10as,10br))-isomer	MeSH

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3220 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

(1S,2R,4R,7Z,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0^{2,4}]tetradec-7-en-13-one

Traditional Name

(1S,2R,4R,7Z,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0^{2,4}]tetradec-7-en-13-one

CAS Registry Number

Not Available

SMILES

[H]C([H])=C1C(=O)O[C@]2([H])[C@@]3([H])O[C@]3(C([H])([H])[H])C([H])([H])C([H])([H])\C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])[C@@]12[H]

InChI Identifier

InChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5-/t11-,12-,13+,15+/m0/s1

InChI Key

KTEXNACQROZXEV-ZRPLFPEYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ambrosia spp.	Plant	KNApSAcK
Anthemis cretica subsp.tenuiloba	Plant	KNApSAcK
Anthemis macedonica	Plant	KNApSAcK
Anthemis melampodina	Plant	KNApSAcK
Anthemis stribrnyi subsp. tracica	Plant	KNApSAcK
Arctotis arctotoides	LOTUS Database	35616633
Arctotis spp.	Plant	KNApSAcK
Carpesium longifolium	Plant	KNApSAcK
Cyathocline purpurea	LOTUS Database	35616633
Eriocephalus kingesii	Plant	KNApSAcK
Laurus nobilis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Magnolia denudata	LOTUS Database	35616633
Magnolia grandiflora	Plant	KNApSAcK
Magnolia nilagirica	LOTUS Database	35616633
Magnolia praecocissima	Plant	KNApSAcK
Magnolia salicifolia	LOTUS Database	35616633
Magnolia virginiana	Plant	KNApSAcK
Michelia baillonii	LOTUS Database	35616633
Michelia champaca	Plant	KNApSAcK
Michelia compressa	LOTUS Database	35616633
Michelia lanuginosa	Plant	KNApSAcK
Michelia yunnanensis	Plant	KNApSAcK
Pentanema aschersonianum	LOTUS Database	35616633
Staehelina fruticosa	Plant	KNApSAcK
Tanacetum argenteum	LOTUS Database	35616633
Tanacetum densum	LOTUS Database	35616633
Tanacetum parthenium	Plant	KNApSAcK
Tanacetum vulgare	LOTUS Database	35616633
Tarchonanthus camphoratus	LOTUS Database	35616633
Tripterygium wilfordii	Plant	KNApSAcK

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
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Oxolane
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	3.03	ALOGPS
logP	3.07	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.55 m³·mol⁻¹	ChemAxon
Polarizability	27.1 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

5584841

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Parthenolide

METLIN ID

Not Available

PubChem Compound

5420804

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wong, H.-F., et al. (2002). Wong, H.-F., e al, Phytochemistry 59, 529 (2002). Phytochem..

Showing NP-Card for parthenolide (NP0028992)

MOL for NP0028992 (parthenolide)

3D MOL for NP0028992 (parthenolide)

3D SDF for NP0028992 (parthenolide)

3D-SDF for NP0028992 (parthenolide)

PDB for NP0028992 (parthenolide)

3D PDB for NP0028992 (parthenolide)

SMILES for NP0028992 (parthenolide)

INCHI for NP0028992 (parthenolide)

Structure for NP0028992 (parthenolide)

3D Structure for NP0028992 (parthenolide)