NP-MRD: Showing NP-Card for parthenin (NP0024770)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-19 17:04:04 UTC

Updated at

2021-06-29 23:49:18 UTC

NP-MRD ID

NP0024770

Secondary Accession Numbers

None

Natural Product Identification

Common Name

parthenin

Provided By

JEOL Database JEOL Logo

Description

parthenin is found in Ambrosia maritima, Ambrosia polystachya, Stylissa carteri, Dichrocephala integrifolia, Ambrosia monogyra, pseudoguaianolid and Stylissa massa. parthenin was first documented in 2014 (PMID: 25196075). Based on a literature review very few articles have been published on Parthenin (PMID: 34285252) (PMID: 34099902) (PMID: 33034953) (PMID: 32686900) (PMID: 32664345) (PMID: 29529439).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119043D          

 37 39  0  0  0  0            999 V2000
    3.2483    2.6222   -2.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052    1.6731   -2.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4330    1.3761   -3.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917    1.7509   -4.9038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4389    0.5687   -3.3079 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599    0.4913   -1.8639 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9117    0.7918   -1.4651 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8689   -0.4083   -1.3512 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8178   -1.1249    0.0024 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5651   -1.9717    0.3166 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6838   -3.3734   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2393   -1.2139    0.0737 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3261   -0.0032    0.8514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -1.8953    0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1035   -1.5718   -0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -0.7243   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4362   -0.0931   -1.8711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1437   -0.8440   -1.3891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0318   -1.9636   -2.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4230    3.2070   -3.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8654    2.8358   -1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1751    1.3195   -1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363    1.3658   -0.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8985   -0.0375   -1.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378   -1.1164   -2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9424   -0.3734    0.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7035   -1.7695    0.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6188   -2.1405    1.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7654   -3.9528   -0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4847   -3.9270    0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466   -3.3566   -1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3329   -0.2451    1.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976   -2.4997    1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1290   -1.8333    0.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6516   -1.7407   -3.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868   -2.0957   -2.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3892   -2.9283   -2.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  0  0  0  0
 18 12  1  0  0  0  0
 18  6  1  0  0  0  0
 10  9  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
 12 10  1  0  0  0  0
 16 17  2  0  0  0  0
  9  8  1  0  0  0  0
  3  4  2  0  0  0  0
 12 14  1  0  0  0  0
  2  1  2  3  0  0  0
 14 15  2  0  0  0  0
 10 11  1  0  0  0  0
 15 16  1  0  0  0  0
 18 19  1  6  0  0  0
 16 18  1  0  0  0  0
 12 13  1  1  0  0  0
  6  5  1  0  0  0  0
  7  2  1  0  0  0  0
 10 28  1  1  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
  8 24  1  0  0  0  0
  8 25  1  0  0  0  0
 14 33  1  0  0  0  0
 15 34  1  0  0  0  0
  7 23  1  1  0  0  0
  6 22  1  1  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 19 35  1  0  0  0  0
 19 36  1  0  0  0  0
 19 37  1  0  0  0  0
 13 32  1  0  0  0  0
M  END

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    3.2483    2.6222   -2.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052    1.6731   -2.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4330    1.3761   -3.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917    1.7509   -4.9038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4389    0.5687   -3.3079 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599    0.4913   -1.8639 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9117    0.7918   -1.4651 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8689   -0.4083   -1.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8178   -1.1249    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5651   -1.9717    0.3166 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6838   -3.3734   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2393   -1.2139    0.0737 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3261   -0.0032    0.8514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -1.8953    0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1035   -1.5718   -0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -0.7243   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4362   -0.0931   -1.8711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1437   -0.8440   -1.3891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0318   -1.9636   -2.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4230    3.2070   -3.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8654    2.8358   -1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1751    1.3195   -1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363    1.3658   -0.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8985   -0.0375   -1.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378   -1.1164   -2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9424   -0.3734    0.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7035   -1.7695    0.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6188   -2.1405    1.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7654   -3.9528   -0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4847   -3.9270    0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466   -3.3566   -1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3329   -0.2451    1.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976   -2.4997    1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1290   -1.8333    0.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6516   -1.7407   -3.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868   -2.0957   -2.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3892   -2.9283   -2.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  7  8  1  0
 18 12  1  0
 18  6  1  0
 10  9  1  0
  5  3  1  0
  3  2  1  0
 12 10  1  0
 16 17  2  0
  9  8  1  0
  3  4  2  0
 12 14  1  0
  2  1  2  3
 14 15  2  0
 10 11  1  0
 15 16  1  0
 18 19  1  6
 16 18  1  0
 12 13  1  1
  6  5  1  0
  7  2  1  0
 10 28  1  1
  9 26  1  0
  9 27  1  0
  8 24  1  0
  8 25  1  0
 14 33  1  0
 15 34  1  0
  7 23  1  1
  6 22  1  1
  1 20  1  0
  1 21  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 13 32  1  0
M  END


  Mrv1652306192119043D          

 37 39  0  0  0  0            999 V2000
    3.2483    2.6222   -2.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052    1.6731   -2.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4330    1.3761   -3.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917    1.7509   -4.9038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4389    0.5687   -3.3079 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599    0.4913   -1.8639 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9117    0.7918   -1.4651 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8689   -0.4083   -1.3512 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8178   -1.1249    0.0024 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5651   -1.9717    0.3166 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6838   -3.3734   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2393   -1.2139    0.0737 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3261   -0.0032    0.8514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -1.8953    0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1035   -1.5718   -0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -0.7243   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4362   -0.0931   -1.8711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1437   -0.8440   -1.3891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0318   -1.9636   -2.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4230    3.2070   -3.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8654    2.8358   -1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1751    1.3195   -1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363    1.3658   -0.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8985   -0.0375   -1.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378   -1.1164   -2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9424   -0.3734    0.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7035   -1.7695    0.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6188   -2.1405    1.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7654   -3.9528   -0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4847   -3.9270    0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466   -3.3566   -1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3329   -0.2451    1.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976   -2.4997    1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1290   -1.8333    0.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6516   -1.7407   -3.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868   -2.0957   -2.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3892   -2.9283   -2.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  0  0  0  0
 18 12  1  0  0  0  0
 18  6  1  0  0  0  0
 10  9  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
 12 10  1  0  0  0  0
 16 17  2  0  0  0  0
  9  8  1  0  0  0  0
  3  4  2  0  0  0  0
 12 14  1  0  0  0  0
  2  1  2  3  0  0  0
 14 15  2  0  0  0  0
 10 11  1  0  0  0  0
 15 16  1  0  0  0  0
 18 19  1  6  0  0  0
 16 18  1  0  0  0  0
 12 13  1  1  0  0  0
  6  5  1  0  0  0  0
  7  2  1  0  0  0  0
 10 28  1  1  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
  8 24  1  0  0  0  0
  8 25  1  0  0  0  0
 14 33  1  0  0  0  0
 15 34  1  0  0  0  0
  7 23  1  1  0  0  0
  6 22  1  1  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 19 35  1  0  0  0  0
 19 36  1  0  0  0  0
 19 37  1  0  0  0  0
 13 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0024770

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]12C([H])=C([H])C(=O)[C@@]1(C([H])([H])[H])[C@]1([H])OC(=O)C(=C([H])[H])[C@]1([H])C([H])([H])C([H])([H])[C@]2([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O4/c1-8-4-5-10-9(2)13(17)19-12(10)14(3)11(16)6-7-15(8,14)18/h6-8,10,12,18H,2,4-5H2,1,3H3/t8-,10-,12+,14-,15+/m0/s1

> <INCHI_KEY>
LLQCRTZROWMVOL-JISBIHODSA-N

> <FORMULA>
C15H18O4

> <MOLECULAR_WEIGHT>
262.305

> <EXACT_MASS>
262.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.090474238527825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,6S,6aS,9aS,9bR)-6a-hydroxy-6,9a-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,6H,6aH,9H,9aH,9bH-azuleno[4,5-b]furan-2,9-dione

> <ALOGPS_LOGP>
0.80

> <JCHEM_LOGP>
2.266630146333333

> <ALOGPS_LOGS>
-2.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.502131571100183

> <JCHEM_PKA_STRONGEST_BASIC>
-3.453967650800781

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
69.3495

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
parthenin

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 39  0  0  0  0  0  0  0  0999 V2000
    3.2483    2.6222   -2.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052    1.6731   -2.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4330    1.3761   -3.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917    1.7509   -4.9038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4389    0.5687   -3.3079 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599    0.4913   -1.8639 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9117    0.7918   -1.4651 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8689   -0.4083   -1.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8178   -1.1249    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5651   -1.9717    0.3166 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6838   -3.3734   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2393   -1.2139    0.0737 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3261   -0.0032    0.8514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -1.8953    0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1035   -1.5718   -0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -0.7243   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4362   -0.0931   -1.8711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1437   -0.8440   -1.3891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0318   -1.9636   -2.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4230    3.2070   -3.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8654    2.8358   -1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1751    1.3195   -1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363    1.3658   -0.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8985   -0.0375   -1.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378   -1.1164   -2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9424   -0.3734    0.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7035   -1.7695    0.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6188   -2.1405    1.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7654   -3.9528   -0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4847   -3.9270    0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466   -3.3566   -1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3329   -0.2451    1.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976   -2.4997    1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1290   -1.8333    0.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6516   -1.7407   -3.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868   -2.0957   -2.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3892   -2.9283   -2.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  7  8  1  0
 18 12  1  0
 18  6  1  0
 10  9  1  0
  5  3  1  0
  3  2  1  0
 12 10  1  0
 16 17  2  0
  9  8  1  0
  3  4  2  0
 12 14  1  0
  2  1  2  3
 14 15  2  0
 10 11  1  0
 15 16  1  0
 18 19  1  6
 16 18  1  0
 12 13  1  1
  6  5  1  0
  7  2  1  0
 10 28  1  1
  9 26  1  0
  9 27  1  0
  8 24  1  0
  8 25  1  0
 14 33  1  0
 15 34  1  0
  7 23  1  1
  6 22  1  1
  1 20  1  0
  1 21  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 13 32  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       3.248   2.622  -2.636  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.305   1.673  -2.605  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.433   1.376  -3.758  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.592   1.751  -4.904  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.439   0.569  -3.308  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.460   0.491  -1.864  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.912   0.792  -1.465  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.869  -0.408  -1.351  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.818  -1.125   0.002  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.565  -1.972   0.317  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.684  -3.373  -0.287  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.239  -1.214   0.074  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.326  -0.003   0.851  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.993  -1.895   0.606  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.103  -1.572  -0.063  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.650  -0.724  -1.183  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.436  -0.093  -1.871  0.00  0.00           O+0
HETATM   18  C   UNK     0      -0.144  -0.844  -1.389  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.032  -1.964  -2.448  0.00  0.00           C+0
HETATM   20  H   UNK     0       3.423   3.207  -3.536  0.00  0.00           H+0
HETATM   21  H   UNK     0       3.865   2.836  -1.771  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.175   1.319  -1.515  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.936   1.366  -0.531  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.898  -0.038  -1.456  0.00  0.00           H+0
HETATM   25  H   UNK     0       2.738  -1.116  -2.174  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.942  -0.373   0.794  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.704  -1.770   0.081  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.619  -2.140   1.404  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.765  -3.953  -0.156  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.485  -3.927   0.218  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.947  -3.357  -1.346  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.333  -0.245   1.795  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.998  -2.500   1.503  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.129  -1.833   0.126  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.652  -1.741  -3.326  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.987  -2.096  -2.815  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.389  -2.928  -2.072  0.00  0.00           H+0
CONECT    1    2   20   21                                                  
CONECT    2    3    1    7                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    7   18    5   22                                             
CONECT    7    6    8    2   23                                             
CONECT    8    7    9   24   25                                             
CONECT    9   10    8   26   27                                             
CONECT   10    9   12   11   28                                             
CONECT   11   10   29   30   31                                             
CONECT   12   18   10   14   13                                             
CONECT   13   12   32                                                       
CONECT   14   12   15   33                                                  
CONECT   15   14   16   34                                                  
CONECT   16   17   15   18                                                  
CONECT   17   16                                                            
CONECT   18   12    6   19   16                                             
CONECT   19   18   35   36   37                                             
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    6                                                            
CONECT   23    7                                                            
CONECT   24    8                                                            
CONECT   25    8                                                            
CONECT   26    9                                                            
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   11                                                            
CONECT   30   11                                                            
CONECT   31   11                                                            
CONECT   32   13                                                            
CONECT   33   14                                                            
CONECT   34   15                                                            
CONECT   35   19                                                            
CONECT   36   19                                                            
CONECT   37   19                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

RDKit          3D

37 39  0  0  0  0  0  0  0  0999 V2000
    3.2483    2.6222   -2.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3052    1.6731   -2.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4330    1.3761   -3.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5917    1.7509   -4.9038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4389    0.5687   -3.3079 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599    0.4913   -1.8639 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9117    0.7918   -1.4651 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8689   -0.4083   -1.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8178   -1.1249    0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5651   -1.9717    0.3166 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6838   -3.3734   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2393   -1.2139    0.0737 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3261   -0.0032    0.8514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9928   -1.8953    0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1035   -1.5718   -0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -0.7243   -1.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4362   -0.0931   -1.8711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1437   -0.8440   -1.3891 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0318   -1.9636   -2.4481 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4230    3.2070   -3.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8654    2.8358   -1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1751    1.3195   -1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9363    1.3658   -0.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8985   -0.0375   -1.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7378   -1.1164   -2.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9424   -0.3734    0.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7035   -1.7695    0.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6188   -2.1405    1.4043 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7654   -3.9528   -0.1559 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4847   -3.9270    0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9466   -3.3566   -1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3329   -0.2451    1.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976   -2.4997    1.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1290   -1.8333    0.1256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6516   -1.7407   -3.3265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868   -2.0957   -2.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3892   -2.9283   -2.0716 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  7  8  1  0
 18 12  1  0
 18  6  1  0
 10  9  1  0
  5  3  1  0
  3  2  1  0
 12 10  1  0
 16 17  2  0
  9  8  1  0
  3  4  2  0
 12 14  1  0
  2  1  2  3
 14 15  2  0
 10 11  1  0
 15 16  1  0
 18 19  1  6
 16 18  1  0
 12 13  1  1
  6  5  1  0
  7  2  1  0
 10 28  1  1
  9 26  1  0
  9 27  1  0
  8 24  1  0
  8 25  1  0
 14 33  1  0
 15 34  1  0
  7 23  1  1
  6 22  1  1
  1 20  1  0
  1 21  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 19 35  1  0
 19 36  1  0
 19 37  1  0
 13 32  1  0
M  END

View in JSmol

Synonyms

Value	Source
Hymenin	MeSH
Parthenin, 3as-(3aalpha,6beta,6abeta,9beta,9balpha)-isomer	MeSH

Chemical Formula

C₁₅H₁₈O₄

Average Mass

262.3050 Da

Monoisotopic Mass

262.12051 Da

IUPAC Name

(3aS,6S,6aS,9aS,9bR)-6a-hydroxy-6,9a-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,6H,6aH,9H,9aH,9bH-azuleno[4,5-b]furan-2,9-dione

Traditional Name

parthenin

CAS Registry Number

Not Available

SMILES

[H]O[C@@]12C([H])=C([H])C(=O)[C@@]1(C([H])([H])[H])[C@]1([H])OC(=O)C(=C([H])[H])[C@]1([H])C([H])([H])C([H])([H])[C@]2([H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H18O4/c1-8-4-5-10-9(2)13(17)19-12(10)14(3)11(16)6-7-15(8,14)18/h6-8,10,12,18H,2,4-5H2,1,3H3/t8-,10-,12+,14-,15+/m0/s1

InChI Key

LLQCRTZROWMVOL-JISBIHODSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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 maritima	LOTUS Database	35616633
Ambrosia polystachya	LOTUS Database	35616633
Ambrosia psilostachya	KNApSAcK Database	22123792
Axinella carteri	-	KNApSAcK
Dichrocephala integrifolia	LOTUS Database	35616633
Hymenoclea monogyra	LOTUS Database	35616633
Iva nevadensis	KNApSAcK Database	22123792
Parthenium confertum	KNApSAcK Database	22123792
Parthenium hysterophorus	KNApSAcK Database	22123792
Parthenium hyterophorus	KNApSAcK Database	22123792
pseudoguaianolid	JEOL database	Das, B., et al, Phytochemistry 68, 2029 (2007)
Stylissa massa	-	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	0.8	ALOGPS
logP	2.27	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	13.5	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.35 m³·mol⁻¹	ChemAxon
Polarizability	27.09 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

C00003344

Chemspider ID

390756

KEGG Compound ID

C09523

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Parthenin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Milugo TK, Tchouassi DP, Kavishe RA, Dinglasan RR, Torto B: Root exudate chemical cues of an invasive plant modulate oviposition behavior and survivorship of a malaria mosquito vector. Sci Rep. 2021 Jul 20;11(1):14785. doi: 10.1038/s41598-021-94043-5. [PubMed:34285252 ]
Rice C, Wolf J, Fleisher DH, Acosta SM, Adkins SW, Bajwa AA, Ziska LH: Recent CO2 levels promote increased production of the toxin parthenin in an invasive Parthenium hysterophorus biotype. Nat Plants. 2021 Jun;7(6):725-729. doi: 10.1038/s41477-021-00938-6. Epub 2021 Jun 7. [PubMed:34099902 ]
Milugo TK, Tchouassi DP, Kavishe RA, Dinglasan RR, Torto B: Derivatization increases mosquito larvicidal activity of the sesquiterpene lactone parthenin isolated from the invasive weed Parthenium hysterophorus. Pest Manag Sci. 2021 Feb;77(2):659-665. doi: 10.1002/ps.6131. Epub 2020 Oct 26. [PubMed:33034953 ]
Kaur M, Gupta KB, Thakur S, Kaur S, Dhiman M: Parthenium hysterophorus mediated inflammation and hyper-responsiveness via NF-kappaB pathway in human A549 lung cancer cell line. Environ Toxicol. 2020 Nov;35(11):1241-1250. doi: 10.1002/tox.22989. Epub 2020 Jul 20. [PubMed:32686900 ]
Bajwa AA, Weston PA, Gurusinghe S, Latif S, Adkins SW, Weston LA: Toxic Potential and Metabolic Profiling of Two Australian Biotypes of the Invasive Plant Parthenium Weed (Parthenium hysterophorus L.). Toxins (Basel). 2020 Jul 10;12(7). pii: toxins12070447. doi: 10.3390/toxins12070447. [PubMed:32664345 ]
Belz RG, Patama M, Sinkkonen A: Low doses of six toxicants change plant size distribution in dense populations of Lactuca sativa. Sci Total Environ. 2018 Aug 1;631-632:510-523. doi: 10.1016/j.scitotenv.2018.02.336. Epub 2018 Mar 16. [PubMed:29529439 ]
Akhtar N, Verma KK, Sharma A: Immunogenetics of cytokine genes in parthenium dermatitis: a review. Eur Ann Allergy Clin Immunol. 2018 Mar;50(2):59-65. doi: 10.23822/EurAnnACI.1764-1489.40. Epub 2017 Nov 27. [PubMed:29384111 ]
Bozicevic A, De Mieri M, Nassenstein C, Wiegand S, Hamburger M: Secondary Metabolites in Allergic Plant Pollen Samples Modulate Afferent Neurons and Murine Tracheal Rings. J Nat Prod. 2017 Nov 22;80(11):2953-2961. doi: 10.1021/acs.jnatprod.7b00495. Epub 2017 Nov 7. [PubMed:29112407 ]
Balaich JN, Mathias DK, Torto B, Jackson BT, Tao D, Ebrahimi B, Tarimo BB, Cheseto X, Foster WA, Dinglasan RR: The Nonartemisinin Sesquiterpene Lactones Parthenin and Parthenolide Block Plasmodium falciparum Sexual Stage Transmission. Antimicrob Agents Chemother. 2016 Mar 25;60(4):2108-17. doi: 10.1128/AAC.02002-15. Print 2016 Apr. [PubMed:26787692 ]
Belz RG: Investigating a Potential Auxin-Related Mode of Hormetic/Inhibitory Action of the Phytotoxin Parthenin. J Chem Ecol. 2016 Jan;42(1):71-83. doi: 10.1007/s10886-015-0662-y. Epub 2015 Dec 19. [PubMed:26686984 ]
Nyasembe VO, Cheseto X, Kaplan F, Foster WA, Teal PE, Tumlinson JH, Borgemeister C, Torto B: The Invasive American Weed Parthenium hysterophorus Can Negatively Impact Malaria Control in Africa. PLoS One. 2015 Sep 14;10(9):e0137836. doi: 10.1371/journal.pone.0137836. eCollection 2015. [PubMed:26367123 ]
Goswami A, Shah BA, Batra N, Kumar A, Guru SK, Bhushan S, Malik FA, Joshi A, Singh J: Multiple Pharmacological Properties of a Novel Parthenin Analog P16 as Evident by its Cytostatic and Antiangiogenic Potential Against Pancreatic Adenocarcinoma PANC -1 Cells. Anticancer Agents Med Chem. 2016;16(6):771-80. doi: 10.2174/1871520615666150824153906. [PubMed:26299660 ]
Goswami A, Shah BA, Kumar A, Rizvi MA, Kumar S, Bhushan S, Malik FA, Batra N, Joshi A, Singh J: Antiproliferative potential of a novel parthenin analog P16 as evident by apoptosis accompanied by down-regulation of PI3K/AKT and ERK pathways in human acute lymphoblastic leukemia MOLT-4 cells. Chem Biol Interact. 2014 Oct 5;222:60-7. doi: 10.1016/j.cbi.2014.08.011. Epub 2014 Sep 6. [PubMed:25196075 ]
Khazir J, Hyder I, Gayatri JL, Prasad Yandrati L, Nalla N, Chasoo G, Mahajan A, Saxena AK, Alam MS, Qazi GN, Sampath Kumar HM: Design and synthesis of novel 1,2,3-triazole derivatives of coronopilin as anti-cancer compounds. Eur J Med Chem. 2014 Jul 23;82:255-62. doi: 10.1016/j.ejmech.2014.05.053. Epub 2014 May 24. [PubMed:24910974 ]
Das, B., et al. (2007). Das, B., et al, Phytochemistry 68, 2029 (2007). Phytochem..

Showing NP-Card for parthenin (NP0024770)

MOL for NP0024770 (parthenin)

3D MOL for NP0024770 (parthenin)

3D SDF for NP0024770 (parthenin)

3D-SDF for NP0024770 (parthenin)

PDB for NP0024770 (parthenin)

3D PDB for NP0024770 (parthenin)

SMILES for NP0024770 (parthenin)

INCHI for NP0024770 (parthenin)

Structure for NP0024770 (parthenin)

3D Structure for NP0024770 (parthenin)