NP-MRD: Showing NP-Card for Picrotin (NP0051948)

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Record Information

Version

2.0

Created at

2022-04-27 23:09:39 UTC

Updated at

2022-04-27 23:09:39 UTC

NP-MRD ID

NP0051948

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Picrotin

Description

Picrotin belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Picrotin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Picrotin is found in Anamirta cocculus , Anamirta paniculata, Cocculus indicus, Diphylleia grayi, Juniperus sabina and Podophyllum peltatum . Picrotin was first documented in 2003 (PMID: 12660352). Based on a literature review a significant number of articles have been published on picrotin (PMID: 29069925) (PMID: 23397268) (PMID: 23079787) (PMID: 21059362) (PMID: 17405877) (PMID: 17714449).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 44  0  0  0  0  0  0  0  0999 V2000
    2.9856    1.0148    0.8285 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1032    0.7107   -0.3916 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0874    0.5056   -1.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3207    1.7846   -0.7130 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4271   -0.5615   -0.1407 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5347   -0.6191    1.0670 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0145   -2.0100    0.8694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3079   -2.7773    1.7993 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0981   -2.1909   -0.5047 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5032   -1.0798   -1.1937 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6329   -0.1391   -1.5013 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5776   -0.8678   -2.2664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3251   -1.6313   -1.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8525   -2.7375   -1.6477 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3730   -0.9118   -0.1310 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6011   -0.5682    0.4179 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4837   -1.2067    1.1648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6732   -0.2213    1.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6431    0.2962    0.9902 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3358    1.5899    1.4086 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3956    0.2529   -0.2934 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2314    1.4859   -0.4952 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2670    0.0476    1.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9354    1.4879    0.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4235    1.5923    1.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2959   -0.5939   -1.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6902    0.9058   -2.4950 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0681    0.9659   -1.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7103    2.5874   -0.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114   -1.3508    0.0125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0391   -0.4986    2.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0004   -1.4155   -2.1053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2783    0.7644   -2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9400   -1.9997    1.7751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1874   -0.7606    2.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3121    0.6131    2.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8186    2.2867    0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7256    1.7357    0.4701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7143    2.3173   -0.9682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0812    1.1964   -1.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  6
  2  5  1  0
  5 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  6 19  1  0
 19 20  1  1
 19 18  1  0
 18 17  1  0
 17 16  1  0
 15 16  1  6
 15 13  1  0
 13 14  2  0
 13 12  1  0
 12 11  1  0
 11 21  1  0
 21 22  1  6
  6  5  1  0
 21 19  1  0
 11 10  1  0
 15 17  1  0
 21 15  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  1
 10 32  1  6
  6 31  1  1
 20 37  1  0
 18 35  1  0
 18 36  1  0
 17 34  1  6
 11 33  1  6
 22 38  1  0
 22 39  1  0
 22 40  1  0
M  END


  Mrv1652304282201092D          

 22 26  0  0  1  0            999 V2000
    2.0414    0.2853    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8770    0.5353    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1555    1.4289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7902    1.8365    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8644    1.7419    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5795    0.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7279    0.8295    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4440    1.5992    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1065    2.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.9756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -0.0277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0181   -0.5581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4308   -0.3462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3807    1.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0040    2.6124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6850    1.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3219    2.1190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6861    0.5369    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1401    1.6192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0455    1.6723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6868    0.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8063    2.4946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  6  0  0  0
  7 10  1  6  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  1 13  1  1  0  0  0
  6 14  1  6  0  0  0
  5 15  1  6  0  0  0
  4 16  1  1  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  2 18  1  1  0  0  0
  3 19  1  6  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051948

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)[C@@H]1[C@H]2OC(=O)[C@@H]1[C@]1(O)C[C@H]3O[C@]33C(=O)O[C@H]2[C@]13C

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O7/c1-12(2,18)6-7-10(16)20-8(6)9-13(3)14(7,19)4-5-15(13,22-5)11(17)21-9/h5-9,18-19H,4H2,1-3H3/t5-,6+,7-,8-,9-,13-,14-,15+/m1/s1

> <INCHI_KEY>
RYEFFICCPKWYML-QCGISDTRSA-N

> <FORMULA>
C15H18O7

> <MOLECULAR_WEIGHT>
310.302

> <EXACT_MASS>
310.10525292

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.590284024495507

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3R,5S,8S,9R,12S,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1^{9,12}.0^{3,5}.0^{5,13}]tetradecane-6,11-dione

> <ALOGPS_LOGP>
0.09

> <JCHEM_LOGP>
-1.0787521719999993

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.97242373417302

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.596322447809218

> <JCHEM_PKA_STRONGEST_BASIC>
-2.822292376099419

> <JCHEM_POLAR_SURFACE_AREA>
105.59

> <JCHEM_REFRACTIVITY>
68.2899

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.45e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,5S,8S,9R,12S,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1^{9,12}.0^{3,5}.0^{5,13}]tetradecane-6,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       3.811   0.532   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.370   0.999   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.890   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.208   3.428   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.480   3.252   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.948   1.773   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.359   1.548   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.829   2.985   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.065   3.983   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.173   1.821   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.229  -0.052   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.034  -1.042   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.671  -0.646   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.444   1.996   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.741   4.876   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.879   2.494   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.067   3.955   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.881   1.002   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.728   3.023   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.418   3.122   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.749   1.644   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.105   4.657   0.000  0.00  0.00           O+0
CONECT    1    2    6   13                                                  
CONECT    2    1    3   18                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6    9   15                                             
CONECT    6    5    1    7   14                                             
CONECT    7    6    8   10   11                                             
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8    7                                                       
CONECT   11    7   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    1                                                       
CONECT   14    6                                                            
CONECT   15    5                                                            
CONECT   16    4   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    2                                                       
CONECT   19    3   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₇

Average Mass

310.3020 Da

Monoisotopic Mass

310.10525 Da

IUPAC Name

(1R,3R,5S,8S,9R,12S,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1^{9,12}.0^{3,5}.0^{5,13}]tetradecane-6,11-dione

Traditional Name

(1R,3R,5S,8S,9R,12S,13R,14S)-1-hydroxy-14-(2-hydroxypropan-2-yl)-13-methyl-4,7,10-trioxapentacyclo[6.4.1.1^{9,12}.0^{3,5}.0^{5,13}]tetradecane-6,11-dione

CAS Registry Number

Not Available

SMILES

CC(C)(O)[C@@H]1[C@H]2OC(=O)[C@@H]1[C@]1(O)C[C@H]3O[C@]33C(=O)O[C@H]2[C@]13C

InChI Identifier

InChI=1S/C15H18O7/c1-12(2,18)6-7-10(16)20-8(6)9-13(3)14(7,19)4-5-15(13,22-5)11(17)21-9/h5-9,18-19H,4H2,1-3H3/t5-,6+,7-,8-,9-,13-,14-,15+/m1/s1

InChI Key

RYEFFICCPKWYML-QCGISDTRSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anamirta cocculus	Plant	KNApSAcK
Anamirta paniculata	Plant	KNApSAcK
Cocculus indicus	Plant	KNApSAcK
Diphylleia grayi	Plant	KNApSAcK
Juniperus sabina	Plant	KNApSAcK
Podophyllum peltatum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Substituents

Furopyran
Caprolactone
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Oxane
Pyran
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Furan
Carboxylic acid ester
Lactone
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Organooxygen compound
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

furopyran (CHEBI:8205 )
Sesquiterpenoids (C15) (C09528 )

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	0.09	ALOGPS
logP	-1.1	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	13.6	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.59 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.29 m³·mol⁻¹	ChemAxon
Polarizability	28.59 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

C00003349

Chemspider ID

390759

KEGG Compound ID

C09528

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Picrotoxin

METLIN ID

Not Available

PubChem Compound

442291

PDB ID

Not Available

ChEBI ID

8205

Good Scents ID

Not Available

References

General References

Yang M, Chen LJ, Zhang Y, Chen YG: Two new picrotoxane-type sesquiterpenoid lactones from Dendrobium williamsonii. J Asian Nat Prod Res. 2019 Feb;21(2):129-133. doi: 10.1080/10286020.2017.1394294. Epub 2017 Oct 25. [PubMed:29069925 ]
Rawat JM, Rawat B, Mehrotra S: Plant regeneration, genetic fidelity, and active ingredient content of encapsulated hairy roots of Picrorhiza kurrooa Royle ex Benth. Biotechnol Lett. 2013 Jun;35(6):961-8. doi: 10.1007/s10529-013-1152-3. Epub 2013 Feb 10. [PubMed:23397268 ]
Li P, Slaughter MM: Gating effects on picrotin block of glycine receptors. Neuroreport. 2012 Dec 5;23(17):1017-20. doi: 10.1097/WNR.0b013e32835a8629. [PubMed:23079787 ]
Thompson AJ, Jarvis GE, Duke RK, Johnston GA, Lummis SC: Ginkgolide B and bilobalide block the pore of the 5-HT(3)receptor at a location that overlaps the picrotoxin binding site. Neuropharmacology. 2011 Feb-Mar;60(2-3):488-95. doi: 10.1016/j.neuropharm.2010.11.003. Epub 2010 Nov 5. [PubMed:21059362 ]
Wang DS, Buckinx R, Lecorronc H, Mangin JM, Rigo JM, Legendre P: Mechanisms for picrotoxinin and picrotin blocks of alpha2 homomeric glycine receptors. J Biol Chem. 2007 Jun 1;282(22):16016-35. doi: 10.1074/jbc.M701502200. Epub 2007 Apr 3. [PubMed:17405877 ]
Yang Z, Cromer BA, Harvey RJ, Parker MW, Lynch JW: A proposed structural basis for picrotoxinin and picrotin binding in the glycine receptor pore. J Neurochem. 2007 Oct;103(2):580-9. doi: 10.1111/j.1471-4159.2007.04850.x. Epub 2007 Aug 20. [PubMed:17714449 ]
Jablonski JE, Jackson LS: Stability of picrotoxin during yogurt manufacture and storage. J Food Sci. 2008 Oct;73(8):T121-8. doi: 10.1111/j.1750-3841.2008.00911.x. [PubMed:19019133 ]
Li P, Slaughter M: Glycine receptor subunit composition alters the action of GABA antagonists. Vis Neurosci. 2007 Jul-Aug;24(4):513-21. doi: 10.1017/S0952523807070368. Epub 2007 Jul 23. [PubMed:17659095 ]
Thio LL, Shanmugam A, Isenberg K, Yamada K: Benzodiazepines block alpha2-containing inhibitory glycine receptors in embryonic mouse hippocampal neurons. J Neurophysiol. 2003 Jul;90(1):89-99. doi: 10.1152/jn.00612.2002. Epub 2003 Mar 26. [PubMed:12660352 ]

Showing NP-Card for Picrotin (NP0051948)

MOL for NP0051948 (Picrotin)

3D MOL for NP0051948 (Picrotin)

3D SDF for NP0051948 (Picrotin)

3D-SDF for NP0051948 (Picrotin)

PDB for NP0051948 (Picrotin)

3D PDB for NP0051948 (Picrotin)

SMILES for NP0051948 (Picrotin)

INCHI for NP0051948 (Picrotin)

Structure for NP0051948 (Picrotin)

3D Structure for NP0051948 (Picrotin)