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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2018-06-07 00:54:20 UTC

Update Date

2022-03-07 03:18:15 UTC

HMDB ID

HMDB0240279

Secondary Accession Numbers

None

Metabolite 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 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

HMDB0240279
     RDKit          3D
Picrotin
 40 44  0  0  0  0  0  0  0  0999 V2000
    3.0068    1.1549    1.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764    0.0070    0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1437   -1.0252    0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828   -0.5096    1.7342 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3494    0.5717   -0.4205 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3966    1.6491   -0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3713    1.7818   -1.2429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2334    0.6384   -2.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5512    0.4115   -3.2085 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4149   -0.3726   -1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6562   -0.9528   -0.2920 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2106   -2.1023    0.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7942   -1.3980   -1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8416   -0.3182   -1.1029 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7110   -0.2975   -0.0102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5558    0.4694   -0.0273 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5952    1.9071    0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3902    2.7091   -0.3728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5988    2.2456    1.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6003    1.2104    1.0155 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3231   -0.0367    0.6722 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7957   -0.8159    1.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2369    1.9091    1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5215    0.8374    2.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6596    1.6179    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3636   -0.9733   -0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1284   -0.9809    0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7442   -2.0468    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0544   -1.1684    2.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0179    0.9845   -1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8424    2.5976    0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9276   -1.1541   -1.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247   -2.9261   -0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014   -1.4905   -2.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2448   -2.3447   -0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3144    0.0588   -2.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1816    1.1737    2.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624   -0.1814    2.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0805   -1.6645    2.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8283   -1.1755    1.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 16 15  1  1
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 10  5  1  0
 21 11  1  0
 20  6  1  0
 16 14  1  0
 21 16  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  6
  6 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  6
 20 37  1  1
 22 38  1  0
 22 39  1  0
 22 40  1  0
M  END


  Mrv1652306071803252D          

 24 28  0  0  1  0            999 V2000
    3.9573    1.1769    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5090    0.6017    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1403    1.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9263    0.3758    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2098    1.2925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6975    0.7837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7633    0.0693    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9167   -0.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6708   -0.1839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5284    0.6547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1298    1.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0057   -0.5125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0206   -1.3094    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4961   -1.3187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7496   -0.9958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1317   -1.6017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7769   -0.1713    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9817    0.0068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5697   -0.0663    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3911    0.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0316   -0.1196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2327   -0.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3528   -1.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6465    0.8036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12  8  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 17 15  1  0  0  0  0
 17  2  1  0  0  0  0
 17 18  1  6  0  0  0
  2 18  1  0  0  0  0
 19 17  1  0  0  0  0
 19  4  1  0  0  0  0
 19 12  1  0  0  0  0
 19 20  1  6  0  0  0
  7 21  1  1  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240279

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12C[C@@]3(O)C4[C@@H](C(OC4=O)[C@@]4([H])OC(=O)[C@]1(O2)[C@@]34C)C(C)(C)O

> <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-TZWFEERXSA-N

> <FORMULA>
C15H18O7

> <MOLECULAR_WEIGHT>
310.302

> <EXACT_MASS>
310.10525292

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.599158230477308

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,3R,5S,8S,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>
105.59000000000002

> <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,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

$$$$

HMDB0240279
     RDKit          3D
Picrotin
 40 44  0  0  0  0  0  0  0  0999 V2000
    3.0068    1.1549    1.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764    0.0070    0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1437   -1.0252    0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828   -0.5096    1.7342 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3494    0.5717   -0.4205 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3966    1.6491   -0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3713    1.7818   -1.2429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2334    0.6384   -2.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5512    0.4115   -3.2085 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4149   -0.3726   -1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6562   -0.9528   -0.2920 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2106   -2.1023    0.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7942   -1.3980   -1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8416   -0.3182   -1.1029 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7110   -0.2975   -0.0102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5558    0.4694   -0.0273 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5952    1.9071    0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3902    2.7091   -0.3728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5988    2.2456    1.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6003    1.2104    1.0155 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3231   -0.0367    0.6722 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7957   -0.8159    1.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2369    1.9091    1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5215    0.8374    2.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6596    1.6179    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3636   -0.9733   -0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1284   -0.9809    0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7442   -2.0468    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0544   -1.1684    2.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0179    0.9845   -1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8424    2.5976    0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9276   -1.1541   -1.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247   -2.9261   -0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014   -1.4905   -2.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2448   -2.3447   -0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3144    0.0588   -2.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1816    1.1737    2.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624   -0.1814    2.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0805   -1.6645    2.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8283   -1.1755    1.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 16 15  1  1
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 10  5  1  0
 21 11  1  0
 20  6  1  0
 16 14  1  0
 21 16  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  6
  6 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  6
 20 37  1  1
 22 38  1  0
 22 39  1  0
 22 40  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       7.387   2.197   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       8.417   1.123   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.595   2.083   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.062   0.701   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.592   2.413   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      12.502   1.463   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.625   0.129   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.911  -1.111   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      14.319  -0.343   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.053   1.222   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      15.176   2.306   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.211  -0.957   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0      11.238  -2.444   0.000  0.00  0.00           H+0
HETATM   14  O   UNK     0      10.259  -2.462   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.866  -1.859   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.713  -2.990   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.917  -0.320   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.432   0.013   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.397  -0.124   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.930   0.680   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.259  -0.223   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.768  -1.097   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.859  -1.901   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.540   1.500   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17   18                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6   19                                             
CONECT    5    4                                                            
CONECT    6    4    7   10                                                  
CONECT    7    6    8   21                                                  
CONECT    8    7    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9    6   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   14   19                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    2   18   19                                             
CONECT   18   17    2                                                       
CONECT   19   17    4   12   20                                             
CONECT   20   19                                                            
CONECT   21    7   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   56    0
END

COMPND    HMDB0240279
HETATM    1  C1  UNL     1       3.007   1.155   1.243  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.176   0.007   0.657  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.144  -1.025   0.177  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.483  -0.510   1.734  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.349   0.572  -0.421  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.397   1.649  -0.033  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.371   1.782  -1.243  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.233   0.638  -2.017  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.551   0.411  -3.209  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.415  -0.373  -1.121  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.656  -0.953  -0.292  1.00  0.00           C  
HETATM   12  O4  UNL     1      -0.211  -2.102   0.353  1.00  0.00           O  
HETATM   13  C9  UNL     1      -1.794  -1.398  -1.219  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.842  -0.318  -1.103  1.00  0.00           C  
HETATM   15  O5  UNL     1      -3.711  -0.297  -0.010  1.00  0.00           O  
HETATM   16  C11 UNL     1      -2.556   0.469  -0.027  1.00  0.00           C  
HETATM   17  C12 UNL     1      -2.595   1.907   0.168  1.00  0.00           C  
HETATM   18  O6  UNL     1      -3.390   2.709  -0.373  1.00  0.00           O  
HETATM   19  O7  UNL     1      -1.599   2.246   1.061  1.00  0.00           O  
HETATM   20  C13 UNL     1      -0.600   1.210   1.016  1.00  0.00           C  
HETATM   21  C14 UNL     1      -1.323  -0.037   0.672  1.00  0.00           C  
HETATM   22  C15 UNL     1      -1.796  -0.816   1.882  1.00  0.00           C  
HETATM   23  H1  UNL     1       2.237   1.909   1.581  1.00  0.00           H  
HETATM   24  H2  UNL     1       3.521   0.837   2.169  1.00  0.00           H  
HETATM   25  H3  UNL     1       3.660   1.618   0.503  1.00  0.00           H  
HETATM   26  H4  UNL     1       3.364  -0.973  -0.902  1.00  0.00           H  
HETATM   27  H5  UNL     1       4.128  -0.981   0.722  1.00  0.00           H  
HETATM   28  H6  UNL     1       2.744  -2.047   0.421  1.00  0.00           H  
HETATM   29  H7  UNL     1       2.054  -1.168   2.179  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.018   0.985  -1.204  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.842   2.598   0.256  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.928  -1.154  -1.678  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.425  -2.926  -0.137  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.501  -1.491  -2.260  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.245  -2.345  -0.887  1.00  0.00           H  
HETATM   36  H14 UNL     1      -3.314   0.059  -2.048  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.182   1.174   2.038  1.00  0.00           H  
HETATM   38  H16 UNL     1      -1.662  -0.181   2.807  1.00  0.00           H  
HETATM   39  H17 UNL     1      -1.081  -1.664   2.016  1.00  0.00           H  
HETATM   40  H18 UNL     1      -2.828  -1.175   1.777  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4    5
CONECT    3   26   27   28
CONECT    4   29
CONECT    5    6   10   30
CONECT    6    7   20   31
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   32
CONECT   11   12   13   21
CONECT   12   33
CONECT   13   14   34   35
CONECT   14   15   16   36
CONECT   15   16
CONECT   16   17   21
CONECT   17   18   18   19
CONECT   19   20
CONECT   20   21   37
CONECT   21   22
CONECT   22   38   39   40
END

HMDB0240279
     RDKit          3D
Picrotin
 40 44  0  0  0  0  0  0  0  0999 V2000
    3.0068    1.1549    1.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1764    0.0070    0.6570 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1437   -1.0252    0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4828   -0.5096    1.7342 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3494    0.5717   -0.4205 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3966    1.6491   -0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3713    1.7818   -1.2429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2334    0.6384   -2.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5512    0.4115   -3.2085 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4149   -0.3726   -1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6562   -0.9528   -0.2920 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2106   -2.1023    0.3529 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7942   -1.3980   -1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8416   -0.3182   -1.1029 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7110   -0.2975   -0.0102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5558    0.4694   -0.0273 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5952    1.9071    0.1684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3902    2.7091   -0.3728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5988    2.2456    1.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6003    1.2104    1.0155 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3231   -0.0367    0.6722 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7957   -0.8159    1.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2369    1.9091    1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5215    0.8374    2.1687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6596    1.6179    0.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3636   -0.9733   -0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1284   -0.9809    0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7442   -2.0468    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0544   -1.1684    2.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0179    0.9845   -1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8424    2.5976    0.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9276   -1.1541   -1.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4247   -2.9261   -0.1373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5014   -1.4905   -2.2597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2448   -2.3447   -0.8872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3144    0.0588   -2.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1816    1.1737    2.0381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624   -0.1814    2.8073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0805   -1.6645    2.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8283   -1.1755    1.7774 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 16 15  1  1
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  1
 10  5  1  0
 21 11  1  0
 20  6  1  0
 16 14  1  0
 21 16  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  6
  6 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  6
 20 37  1  1
 22 38  1  0
 22 39  1  0
 22 40  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₇

Average Molecular Weight

310.302

Monoisotopic Molecular Weight

310.10525292

IUPAC Name

(1R,3R,5S,8S,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,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

[H][C@@]12C[C@@]3(O)C4[C@@H](C(OC4=O)[C@@]4([H])OC(=O)[C@]1(O2)[C@@]34C)C(C)(C)O

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-TZWFEERXSA-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: HMDB0240279)

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	0.09	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	28.6 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M-H]-	175.531	31661259
AllCCS	[M+H]+	166.875	31661259
DeepCCS	[M-2H]-	207.906	30932474
DeepCCS	[M+Na]+	182.549	30932474
AllCCS	[M+H]+	166.9	32859911
AllCCS	[M+H-H2O]+	163.8	32859911
AllCCS	[M+NH4]+	169.7	32859911
AllCCS	[M+Na]+	170.5	32859911
AllCCS	[M-H]-	175.5	32859911
AllCCS	[M+Na-2H]-	174.9	32859911
AllCCS	[M+HCOO]-	174.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Picrotin	[H][C@@]12C[C@@]3(O)C4[C@@H](C(OC4=O)[C@@]4([H])OC(=O)[C@]1(O2)[C@@]34C)C(C)(C)O	3658.3	Standard polar	33892256
Picrotin	[H][C@@]12C[C@@]3(O)C4[C@@H](C(OC4=O)[C@@]4([H])OC(=O)[C@]1(O2)[C@@]34C)C(C)(C)O	2149.7	Standard non polar	33892256
Picrotin	[H][C@@]12C[C@@]3(O)C4[C@@H](C(OC4=O)[C@@]4([H])OC(=O)[C@]1(O2)[C@@]34C)C(C)(C)O	2676.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Picrotin,1TMS,isomer #1	CC(C)(O)[C@@H]1C2OC(=O)C1[C@]1(O[Si](C)(C)C)C[C@H]3O[C@]34C(=O)O[C@H]2[C@@]41C	2381.7	Semi standard non polar	33892256
Picrotin,1TMS,isomer #2	CC(C)(O[Si](C)(C)C)[C@@H]1C2OC(=O)C1[C@]1(O)C[C@H]3O[C@]34C(=O)O[C@H]2[C@@]41C	2372.7	Semi standard non polar	33892256
Picrotin,2TMS,isomer #1	CC(C)(O[Si](C)(C)C)[C@@H]1C2OC(=O)C1[C@]1(O[Si](C)(C)C)C[C@H]3O[C@]34C(=O)O[C@H]2[C@@]41C	2468.3	Semi standard non polar	33892256
Picrotin,1TBDMS,isomer #1	CC(C)(O)[C@@H]1C2OC(=O)C1[C@]1(O[Si](C)(C)C(C)(C)C)C[C@H]3O[C@]34C(=O)O[C@H]2[C@@]41C	2606.7	Semi standard non polar	33892256
Picrotin,1TBDMS,isomer #2	CC(C)(O[Si](C)(C)C(C)(C)C)[C@@H]1C2OC(=O)C1[C@]1(O)C[C@H]3O[C@]34C(=O)O[C@H]2[C@@]41C	2606.2	Semi standard non polar	33892256
Picrotin,2TBDMS,isomer #1	CC(C)(O[Si](C)(C)C(C)(C)C)[C@@H]1C2OC(=O)C1[C@]1(O[Si](C)(C)C(C)(C)C)C[C@H]3O[C@]34C(=O)O[C@H]2[C@@]41C	2918.8	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 - Picrotin 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 - Picrotin 10V, Positive-QTOF	splash10-01r6-0092000000-30a807bc030ec76ea5f7	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotin 20V, Positive-QTOF	splash10-002f-0091000000-a9bebdc02788a69a7ec6	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotin 40V, Positive-QTOF	splash10-004i-1390000000-6f5689a2ae261cec9b46	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotin 10V, Negative-QTOF	splash10-0a4i-0059000000-5c02fc2c422bbcaed2b6	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotin 20V, Negative-QTOF	splash10-052f-0092000000-6874d6085bb7e957f320	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotin 40V, Negative-QTOF	splash10-0829-0090000000-62133e4d623ac03aa761	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotin 10V, Positive-QTOF	splash10-03di-0029000000-a0294631856eadece068	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotin 20V, Positive-QTOF	splash10-03xr-0829000000-dc1469cce32093e7b251	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotin 40V, Positive-QTOF	splash10-03di-0159000000-c5105d43b9eb79e70c48	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotin 10V, Negative-QTOF	splash10-0a4i-0009000000-ff1726768fe2bc55c294	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotin 20V, Negative-QTOF	splash10-0a4i-0039000000-93412654f6364f7ba807	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Picrotin 40V, Negative-QTOF	splash10-0a6u-0967000000-49edcba17f4148fdb914	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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

C00003349

Chemspider ID

2297304

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Picrotoxin

METLIN ID

Not Available

PubChem Compound

3032291

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 Picrotin (HMDB0240279)

MOL for HMDB0240279 (Picrotin)

3D MOL for HMDB0240279 (Picrotin)

3D SDF for HMDB0240279 (Picrotin)

3D-SDF for HMDB0240279 (Picrotin)

PDB for HMDB0240279 (Picrotin)

3D PDB for HMDB0240279 (Picrotin)

SMILES for HMDB0240279 (Picrotin)

INCHI for HMDB0240279 (Picrotin)

Structure for HMDB0240279 (Picrotin)

3D Structure for HMDB0240279 (Picrotin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra