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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2018-06-07 00:54:02 UTC

Update Date

2022-03-07 03:18:15 UTC

HMDB ID

HMDB0240274

Secondary Accession Numbers

None

Metabolite 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. Picrotoxinin is soluble (in water) and a very weakly acidic compound (based on its pKa).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0240274
     RDKit          3D
Picrotoxinin
 37 41  0  0  0  0  0  0  0  0999 V2000
    2.6491   -0.4943    1.7439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4182    0.4874    0.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9871    1.8345    1.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    0.4304   -0.2763 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5817    1.4477   -0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1277    1.0181   -1.8218 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5490   -0.2711   -2.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5950   -0.8876   -3.1523 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9738   -0.8101   -0.7191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2988   -1.1708   -0.0613 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1521   -2.0296    1.0207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1310   -1.9778   -1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1116   -0.9791   -1.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3056   -0.7945   -0.8282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2177    0.0705   -0.7786 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4100    1.5018   -1.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1776    1.9961   -1.8561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6075    2.1844   -0.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5964    1.2922    0.3805 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2088   -0.0645    0.3481 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9771   -0.3505    1.6159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2194   -0.3909    2.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3181   -1.4903    1.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1638    2.4639    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9551    1.7270    1.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3076    2.3753    1.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4115    0.6376   -1.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9215    2.4770   -0.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6235   -1.6728   -0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7514   -2.8078    1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6765   -2.8083   -0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5414   -2.3970   -1.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054   -0.9525   -2.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4106    1.6109    1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6685    0.3793    2.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0729   -0.1932    1.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8530   -1.3916    1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 15 14  1  1
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
  9  4  1  0
 20 10  1  0
 19  5  1  0
 15 13  1  0
 20 15  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  6
  5 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 19 34  1  1
 21 35  1  0
 21 36  1  0
 21 37  1  0
M  END

  Mrv1652306071803202D          

 22 26  0  0  1  0            999 V2000
    0.5587   -1.4173    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1900   -0.7116    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3742   -1.2985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1200   -0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8329   -1.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0928   -0.1522    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8873    0.0256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3604    0.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7296    1.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0269    0.7218    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2067    1.5747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8261    0.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8918    0.0880    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0450   -0.5757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7985   -0.1649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6562    0.6730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2471    1.2642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0807   -0.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5225   -0.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7001    0.4704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3007   -0.0474    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4465    0.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
 13 18  1  1  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 21 10  1  0  0  0  0
 21  2  1  0  0  0  0
 21  6  1  0  0  0  0
 21 22  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0240274

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12OC(=O)[C@@]34OC3C[C@@](O)(C3[C@@H](C1OC3=O)C(C)=C)[C@@]24C

> <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-/m0/s1

> <INCHI_KEY>
PIMZUZSSNYHVCU-LJGWEWMTSA-N

> <FORMULA>
C15H16O6

> <MOLECULAR_WEIGHT>
292.287

> <EXACT_MASS>
292.094688235

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.239416635139932

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5S,8S,13R,14R)-1-hydroxy-13-methyl-14-(prop-1-en-2-yl)-4,7,10-trioxapentacyclo[6.4.1.1^{9,12}.0^{3,5}.0^{5,13}]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>
66.33010000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.17e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240274
     RDKit          3D
Picrotoxinin
 37 41  0  0  0  0  0  0  0  0999 V2000
    2.6491   -0.4943    1.7439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4182    0.4874    0.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9871    1.8345    1.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    0.4304   -0.2763 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5817    1.4477   -0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1277    1.0181   -1.8218 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5490   -0.2711   -2.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5950   -0.8876   -3.1523 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9738   -0.8101   -0.7191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2988   -1.1708   -0.0613 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1521   -2.0296    1.0207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1310   -1.9778   -1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1116   -0.9791   -1.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3056   -0.7945   -0.8282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2177    0.0705   -0.7786 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4100    1.5018   -1.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1776    1.9961   -1.8561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6075    2.1844   -0.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5964    1.2922    0.3805 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2088   -0.0645    0.3481 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9771   -0.3505    1.6159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2194   -0.3909    2.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3181   -1.4903    1.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1638    2.4639    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9551    1.7270    1.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3076    2.3753    1.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4115    0.6376   -1.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9215    2.4770   -0.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6235   -1.6728   -0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7514   -2.8078    1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6765   -2.8083   -0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5414   -2.3970   -1.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054   -0.9525   -2.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4106    1.6109    1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6685    0.3793    2.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0729   -0.1932    1.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8530   -1.3916    1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 15 14  1  1
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
  9  4  1  0
 20 10  1  0
 19  5  1  0
 15 13  1  0
 20 15  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  6
  5 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 19 34  1  1
 21 35  1  0
 21 36  1  0
 21 37  1  0
M  END

HEADER    PROTEIN                                 07-JUN-18   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JUN-18         0                                  
HETATM    1  H   UNK     0       1.043  -2.646   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       0.355  -1.328   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.699  -2.424   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.091  -1.822   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -3.421  -2.683   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.040  -0.284   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.523   0.048   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.539   1.157   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.362   2.116   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.050   1.347   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.386   2.939   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.542   1.497   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.665   0.164   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.951  -1.075   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.357  -0.308   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.092   1.256   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.195   2.360   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.151  -0.285   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.975  -1.504   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.307   0.878   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.561  -0.088   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.833   0.684   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14   21                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8   21                                             
CONECT    7    6    8                                                       
CONECT    8    7    6    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   21                                             
CONECT   11   10                                                            
CONECT   12   10   13   16                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13    2   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   12   17                                                  
CONECT   17   16                                                            
CONECT   18   13   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   10    2    6   22                                             
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   52    0
END

COMPND    HMDB0240274
HETATM    1  C1  UNL     1       2.649  -0.494   1.744  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.418   0.487   0.928  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.987   1.834   1.336  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.672   0.430  -0.276  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.582   1.448  -0.517  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.128   1.018  -1.822  1.00  0.00           O  
HETATM    7  C6  UNL     1       0.549  -0.271  -2.089  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.595  -0.888  -3.152  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.974  -0.810  -0.719  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.299  -1.171  -0.061  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.152  -2.030   1.021  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.131  -1.978  -1.086  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.112  -0.979  -1.644  1.00  0.00           C  
HETATM   14  O4  UNL     1      -3.306  -0.794  -0.828  1.00  0.00           O  
HETATM   15  C11 UNL     1      -2.218   0.071  -0.779  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.410   1.502  -1.004  1.00  0.00           C  
HETATM   17  O5  UNL     1      -3.178   1.996  -1.856  1.00  0.00           O  
HETATM   18  O6  UNL     1      -1.607   2.184  -0.123  1.00  0.00           O  
HETATM   19  C13 UNL     1      -0.596   1.292   0.381  1.00  0.00           C  
HETATM   20  C14 UNL     1      -1.209  -0.064   0.348  1.00  0.00           C  
HETATM   21  C15 UNL     1      -1.977  -0.350   1.616  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.219  -0.391   2.688  1.00  0.00           H  
HETATM   23  H2  UNL     1       2.318  -1.490   1.544  1.00  0.00           H  
HETATM   24  H3  UNL     1       3.164   2.464   0.417  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.955   1.727   1.821  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.308   2.375   1.996  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.411   0.638  -1.150  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.921   2.477  -0.563  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.623  -1.673  -0.824  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.751  -2.808   1.004  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.676  -2.808  -0.587  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.541  -2.397  -1.886  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.305  -0.952  -2.727  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.411   1.611   1.419  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.669   0.379   2.405  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.073  -0.193   1.489  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.853  -1.392   1.974  1.00  0.00           H  
CONECT    1    2    2   22   23
CONECT    2    3    4
CONECT    3   24   25   26
CONECT    4    5    9   27
CONECT    5    6   19   28
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   29
CONECT   10   11   12   20
CONECT   11   30
CONECT   12   13   31   32
CONECT   13   14   15   33
CONECT   14   15
CONECT   15   16   20
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20   34
CONECT   20   21
CONECT   21   35   36   37
END

HMDB0240274
     RDKit          3D
Picrotoxinin
 37 41  0  0  0  0  0  0  0  0999 V2000
    2.6491   -0.4943    1.7439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4182    0.4874    0.9283 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9871    1.8345    1.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    0.4304   -0.2763 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5817    1.4477   -0.5166 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1277    1.0181   -1.8218 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5490   -0.2711   -2.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5950   -0.8876   -3.1523 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9738   -0.8101   -0.7191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2988   -1.1708   -0.0613 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1521   -2.0296    1.0207 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1310   -1.9778   -1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1116   -0.9791   -1.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3056   -0.7945   -0.8282 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2177    0.0705   -0.7786 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4100    1.5018   -1.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1776    1.9961   -1.8561 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6075    2.1844   -0.1234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5964    1.2922    0.3805 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2088   -0.0645    0.3481 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9771   -0.3505    1.6159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2194   -0.3909    2.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3181   -1.4903    1.5445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1638    2.4639    0.4172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9551    1.7270    1.8211 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3076    2.3753    1.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4115    0.6376   -1.1505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9215    2.4770   -0.5629 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6235   -1.6728   -0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7514   -2.8078    1.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6765   -2.8083   -0.5869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5414   -2.3970   -1.8857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054   -0.9525   -2.7268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4106    1.6109    1.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6685    0.3793    2.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0729   -0.1932    1.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8530   -1.3916    1.9743 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 15 14  1  1
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  1
  9  4  1  0
 20 10  1  0
 19  5  1  0
 15 13  1  0
 20 15  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  6
  5 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 19 34  1  1
 21 35  1  0
 21 36  1  0
 21 37  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Picrotoxinine	HMDB

Chemical Formula

C₁₅H₁₆O₆

Average Molecular Weight

292.287

Monoisotopic Molecular Weight

292.094688235

IUPAC Name

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

Traditional Name

(1R,5S,8S,13R,14R)-1-hydroxy-13-methyl-14-(prop-1-en-2-yl)-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

[H][C@@]12OC(=O)[C@@]34OC3C[C@@](O)(C3[C@@H](C1OC3=O)C(C)=C)[C@@]24C

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-/m0/s1

InChI Key

PIMZUZSSNYHVCU-LJGWEWMTSA-N

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

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0240274)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	27.24 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M-H]-	171.487	31661259
AllCCS	[M+H]+	164.151	31661259
DeepCCS	[M-2H]-	199.676	30932474
DeepCCS	[M+Na]+	174.498	30932474
AllCCS	[M+H]+	164.2	32859911
AllCCS	[M+H-H2O]+	160.9	32859911
AllCCS	[M+NH4]+	167.2	32859911
AllCCS	[M+Na]+	168.1	32859911
AllCCS	[M-H]-	171.5	32859911
AllCCS	[M+Na-2H]-	170.8	32859911
AllCCS	[M+HCOO]-	170.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Picrotoxinin	[H][C@@]12OC(=O)[C@@]34OC3C[C@@](O)(C3[C@@H](C1OC3=O)C(C)=C)[C@@]24C	3402.6	Standard polar	33892256
Picrotoxinin	[H][C@@]12OC(=O)[C@@]34OC3C[C@@](O)(C3[C@@H](C1OC3=O)C(C)=C)[C@@]24C	2128.6	Standard non polar	33892256
Picrotoxinin	[H][C@@]12OC(=O)[C@@]34OC3C[C@@](O)(C3[C@@H](C1OC3=O)C(C)=C)[C@@]24C	2464.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Picrotoxinin,1TMS,isomer #1	C=C(C)[C@@H]1C2OC(=O)C1[C@]1(O[Si](C)(C)C)CC3O[C@]34C(=O)O[C@H]2[C@@]41C	2202.2	Semi standard non polar	33892256
Picrotoxinin,1TBDMS,isomer #1	C=C(C)[C@@H]1C2OC(=O)C1[C@]1(O[Si](C)(C)C(C)(C)C)CC3O[C@]34C(=O)O[C@H]2[C@@]41C	2434.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Picrotoxinin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Picrotoxinin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotoxinin 10V, Positive-QTOF	splash10-004l-0090000000-064a45635b6cf82b20d7	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotoxinin 20V, Positive-QTOF	splash10-004l-0090000000-9e9eef6032d928d27a60	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotoxinin 40V, Positive-QTOF	splash10-0a7i-3490000000-8f06bee0ccc6b3adbe06	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotoxinin 10V, Negative-QTOF	splash10-0006-0090000000-f4aeafa9e6054e270e7c	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotoxinin 20V, Negative-QTOF	splash10-00dm-0090000000-e25447e67a0d71a2fed2	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotoxinin 40V, Negative-QTOF	splash10-0udi-0090000000-4a25951102eb50a608b4	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotoxinin 10V, Positive-QTOF	splash10-0006-0090000000-27a50d8d1b5d00ef062c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotoxinin 20V, Positive-QTOF	splash10-0006-0090000000-80a20eb420e29d2e1583	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotoxinin 40V, Positive-QTOF	splash10-0006-2190000000-0b28b3a7dc786b5d036d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotoxinin 10V, Negative-QTOF	splash10-0006-0090000000-e2531b222357475903f2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotoxinin 20V, Negative-QTOF	splash10-0006-0090000000-c6b7086e2b5845134570	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotoxinin 40V, Negative-QTOF	splash10-0096-0390000000-4c814fc62ebacb32678d	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00003350

Chemspider ID

29045

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Picrotoxin

METLIN ID

Not Available

PubChem Compound

31306

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Picrotoxinin (HMDB0240274)

MOL for HMDB0240274 (Picrotoxinin)

3D MOL for HMDB0240274 (Picrotoxinin)

3D SDF for HMDB0240274 (Picrotoxinin)

3D-SDF for HMDB0240274 (Picrotoxinin)

PDB for HMDB0240274 (Picrotoxinin)

3D PDB for HMDB0240274 (Picrotoxinin)

SMILES for HMDB0240274 (Picrotoxinin)

INCHI for HMDB0240274 (Picrotoxinin)

Structure for HMDB0240274 (Picrotoxinin)

3D Structure for HMDB0240274 (Picrotoxinin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra