NP-MRD: Showing NP-Card for Picrotoxinin (NP0051949)

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Record Information

Version

2.0

Created at

2022-04-27 23:09:42 UTC

Updated at

2022-04-27 23:09:42 UTC

NP-MRD ID

NP0051949

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Picrotoxinin

Description

Picrotoxinin 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. Thus, picrotoxinin is considered to be an isoprenoid lipid molecule. Picrotoxinin is found in Anamirta cocculus and Cocculus indicus. Picrotoxinin was first documented in 1994 (PMID: 7916140). Picrotoxinin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 12770091) (PMID: 17405877) (PMID: 17675213) (PMID: 17714449) (PMID: 18031737) (PMID: 21505038).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv0541 05041410322D          

 26 30  0  0  1  0            999 V2000
    1.8862    0.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0860   -0.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0893    0.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8577    1.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7057   -0.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2043    0.5774    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5376    0.0262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4695    0.7656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6963   -0.6613    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8105   -0.8021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3295    0.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4533   -1.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3021   -0.1141    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5857    0.6828    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4815   -0.2227    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9413    1.2441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147   -1.5533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267    1.5657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4769   -0.2357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2259   -1.4103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -0.0385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6332    1.1728    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8536    0.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4944    1.5903    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9624   -1.4422    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925   -1.5334    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  1  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 13  3  1  6  0  0  0
 13 10  1  0  0  0  0
 14  4  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15  6  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 11  2  0  0  0  0
 17 12  2  0  0  0  0
 14 18  1  6  0  0  0
 19  9  1  0  0  0  0
 19 11  1  0  0  0  0
 20 10  1  0  0  0  0
 20 12  1  0  0  0  0
 21  6  1  0  0  0  0
 15 21  1  6  0  0  0
  6 22  1  1  0  0  0
  7 23  1  6  0  0  0
  8 24  1  6  0  0  0
  9 25  1  6  0  0  0
 10 26  1  6  0  0  0
M  END

     RDKit          3D

 37 41  0  0  0  0  0  0  0  0999 V2000
    2.6509   -1.6835    0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5497   -0.3910    0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5448    0.4291    0.8997 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5631    0.3008   -0.6039 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4929   -0.4082   -1.3559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0231    0.8460   -2.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531    0.9077   -3.2690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1236    1.7448   -1.0067 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7641    1.3835    0.0714 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0464    0.7629    1.1568 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8239    1.8270    1.7332 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8761    2.1050    0.8540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4117    3.2121    0.7220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1742    0.8558    0.1708 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4481    0.3343    0.1419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870    0.5285   -1.0813 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9252   -0.7467   -1.5003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6797   -0.9037   -0.6095 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6301   -2.2914   -0.3869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1046   -0.1483    0.5996 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7134   -1.0046    1.6841 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4374   -2.1322    0.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0060   -2.3825   -0.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1048    1.3699    1.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3587    0.7295    0.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9788   -0.1376    1.7337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1368    0.8774   -1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8228   -1.1555   -2.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3616    2.2286    0.4097 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5084    0.2204    1.9180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1727    1.0950   -1.8038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6742   -1.5648   -1.2670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7000   -0.7170   -2.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2776   -2.4410    0.5019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9629   -1.1851    2.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0998   -1.9673    1.2986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5733   -0.4979    2.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 17 18  1  0
 18 19  1  1
 18  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  1
 14 20  1  0
 20 21  1  1
  9  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 14 16  1  0
 15 16  1  0
 20 18  1  0
  4  5  1  0
 20 10  1  0
 16 31  1  6
 17 32  1  0
 17 33  1  0
 19 34  1  0
  5 28  1  6
  9 29  1  1
 10 30  1  1
 21 35  1  0
 21 36  1  0
 21 37  1  0
  4 27  1  6
  3 24  1  0
  3 25  1  0
  3 26  1  0
  1 22  1  0
  1 23  1  0
M  END

  Mrv0541 05041410322D          

 26 30  0  0  1  0            999 V2000
    1.8862    0.4413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0860   -0.9117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0893    0.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8577    1.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7057   -0.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2043    0.5774    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5376    0.0262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4695    0.7656    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6963   -0.6613    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8105   -0.8021    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3295    0.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4533   -1.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3021   -0.1141    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5857    0.6828    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4815   -0.2227    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9413    1.2441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147   -1.5533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8267    1.5657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4769   -0.2357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2259   -1.4103    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6584   -0.0385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6332    1.1728    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8536    0.4875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4944    1.5903    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9624   -1.4422    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925   -1.5334    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  5  2  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  1  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 13  3  1  6  0  0  0
 13 10  1  0  0  0  0
 14  4  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15  6  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 11  2  0  0  0  0
 17 12  2  0  0  0  0
 14 18  1  6  0  0  0
 19  9  1  0  0  0  0
 19 11  1  0  0  0  0
 20 10  1  0  0  0  0
 20 12  1  0  0  0  0
 21  6  1  0  0  0  0
 15 21  1  6  0  0  0
  6 22  1  1  0  0  0
  7 23  1  6  0  0  0
  8 24  1  6  0  0  0
  9 25  1  6  0  0  0
 10 26  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051949

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@@]3(O)[C@@]4([H])C(=O)O[C@@]([H])([C@@]5([H])OC(=O)[C@]1(O2)[C@@]35C)[C@@]4([H])C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O6/c1-5(2)7-8-11(16)19-9(7)10-13(3)14(8,18)4-6-15(13,21-6)12(17)20-10/h6-10,18H,1,4H2,2-3H3/t6-,7+,8-,9-,10-,13-,14-,15+/m1/s1

> <INCHI_KEY>
PIMZUZSSNYHVCU-YKWPQBAZSA-N

> <FORMULA>
C15H16O6

> <MOLECULAR_WEIGHT>
292.2839

> <EXACT_MASS>
292.094688244

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.970489243902797

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R,5S,8S,9R,12S,13R,14R)-1-hydroxy-13-methyl-14-(prop-1-en-2-yl)-4,7,10-trioxapentacyclo[6.4.1.1⁹,¹².0³,⁵.0⁵,¹³]tetradecane-6,11-dione

> <ALOGPS_LOGP>
0.24

> <JCHEM_LOGP>
0.0031599750000005436

> <ALOGPS_LOGS>
-1.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.610566740986098

> <JCHEM_PKA_STRONGEST_BASIC>
-3.40653810749268

> <JCHEM_POLAR_SURFACE_AREA>
85.36000000000001

> <JCHEM_REFRACTIVITY>
66.3301

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
picrotoxinin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    5                                                            
CONECT    2    5                                                            
CONECT    3   13                                                            
CONECT    4    6   14                                                       
CONECT    5    1    2    7                                                  
CONECT    6    4   15   21   22                                             
CONECT    7    5    8    9   23                                             
CONECT    8    7   11   14   24                                             
CONECT    9    7   10   19   25                                             
CONECT   10    9   13   20   26                                             
CONECT   11    8   16   19                                                  
CONECT   12   15   17   20                                                  
CONECT   13    3   10   14   15                                             
CONECT   14    4    8   13   18                                             
CONECT   15    6   12   13   21                                             
CONECT   16   11                                                            
CONECT   17   12                                                            
CONECT   18   14                                                            
CONECT   19    9   11                                                       
CONECT   20   10   12                                                       
CONECT   21    6   15                                                       
CONECT   22    6                                                            
CONECT   23    7                                                            
CONECT   24    8                                                            
CONECT   25    9                                                            
CONECT   26   10                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   60    0
END

View in JSmol

Synonyms

Value	Source
(-)-Picrotoxinin	ChEBI
Picrotoxinine	ChEBI
Picrotoxinin	MeSH

Chemical Formula

C₁₅H₁₆O₆

Average Mass

292.2839 Da

Monoisotopic Mass

292.09469 Da

IUPAC Name

(1R,3R,5S,8S,9R,12S,13R,14R)-1-hydroxy-13-methyl-14-(prop-1-en-2-yl)-4,7,10-trioxapentacyclo[6.4.1.1⁹,¹².0³,⁵.0⁵,¹³]tetradecane-6,11-dione

Traditional Name

picrotoxinin

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@@]3(O)[C@@]4([H])C(=O)O[C@@]([H])([C@@]5([H])OC(=O)[C@]1(O2)[C@@]35C)[C@@]4([H])C(C)=C

InChI Identifier

InChI=1S/C15H16O6/c1-5(2)7-8-11(16)19-9(7)10-13(3)14(8,18)4-6-15(13,21-6)12(17)20-10/h6-10,18H,1,4H2,2-3H3/t6-,7+,8-,9-,10-,13-,14-,15+/m1/s1

InChI Key

PIMZUZSSNYHVCU-YKWPQBAZSA-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
Cocculus indicus	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:8206 )
Picrotoxane sesquiterpenoids (C09529 )
Sesquiterpenoids (C15) (C09529 )
Sesquiterpenes (C09529 )
Picrotoxane sesquiterpenoids (LMPR0103540001 )

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	0.24	ALOGPS
logP	0.0032	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	66.33 m³·mol⁻¹	ChemAxon
Polarizability	26.97 Å³	ChemAxon
Number of Rings	5	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

C00003350

Chemspider ID

Not Available

KEGG Compound ID

C09529

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Picrotoxin

METLIN ID

Not Available

PubChem Compound

442292

PDB ID

Not Available

ChEBI ID

8206

Good Scents ID

Not Available

References

General References

Le Corronc H, Alix P, Hue B: Differential sensitivity of two insect GABA-gated chloride channels to dieldrin, fipronil and picrotoxinin. J Insect Physiol. 2002 Apr;48(4):419-431. doi: 10.1016/s0022-1910(02)00061-6. [PubMed:12770091 ]
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 ]
Ju XL, Hao YL, Pei JF, Ozoe Y: Investigation of structural requirements for inhibitory activity at the rat and housefly picrotoxinin binding sites in ionotropic GABA receptors using DISCOtech and CoMFA. Chemosphere. 2007 Oct;69(6):864-71. doi: 10.1016/j.chemosphere.2007.06.040. Epub 2007 Aug 1. [PubMed:17675213 ]
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 ]
Carland JE, Johnston GA, Chebib M: Relative impact of residues at the intracellular and extracellular ends of the human GABAC rho1 receptor M2 domain on picrotoxinin activity. Eur J Pharmacol. 2008 Feb 2;580(1-2):27-35. doi: 10.1016/j.ejphar.2007.10.036. Epub 2007 Oct 25. [PubMed:18031737 ]
Thompson AJ, Duke RK, Lummis SC: Binding sites for bilobalide, diltiazem, ginkgolide, and picrotoxinin at the 5-HT3 receptor. Mol Pharmacol. 2011 Jul;80(1):183-90. doi: 10.1124/mol.111.071415. Epub 2011 Apr 19. [PubMed:21505038 ]
Thompson AJ, Alqazzaz M, Price KL, Weston DA, Lummis SC: Phenylalanine in the pore of the Erwinia ligand-gated ion channel modulates picrotoxinin potency but not receptor function. Biochemistry. 2014 Oct 7;53(39):6183-8. doi: 10.1021/bi5008035. Epub 2014 Sep 19. [PubMed:25238029 ]
Naffaa MM, Samad A: The binding mode of picrotoxinin in GABAA-rho receptors: Insight into the subunit's selectivity in the transmembrane domain. Comput Biol Chem. 2016 Oct;64:202-209. doi: 10.1016/j.compbiolchem.2016.07.003. Epub 2016 Jul 7. [PubMed:27423910 ]
Anthony NM, Holyoke CW Jr, Sattelle DB: Blocking actions of picrotoxinin analogues on insect (Periplaneta americana) GABA receptors. Neurosci Lett. 1994 Apr 25;171(1-2):67-9. doi: 10.1016/0304-3940(94)90606-8. [PubMed:7916140 ]

Showing NP-Card for Picrotoxinin (NP0051949)

MOL for NP0051949 (Picrotoxinin)

3D MOL for NP0051949 (Picrotoxinin)

3D SDF for NP0051949 (Picrotoxinin)

3D-SDF for NP0051949 (Picrotoxinin)

PDB for NP0051949 (Picrotoxinin)

3D PDB for NP0051949 (Picrotoxinin)

SMILES for NP0051949 (Picrotoxinin)

INCHI for NP0051949 (Picrotoxinin)

Structure for NP0051949 (Picrotoxinin)

3D Structure for NP0051949 (Picrotoxinin)