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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:25 UTC

Update Date

2022-03-07 02:53:07 UTC

HMDB ID

HMDB0031779

Secondary Accession Numbers

HMDB31779

Metabolite Identification

Common Name

Isoprothiolane

Description

Isoprothiolane, also known as IPT or fudiolan, belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups. Based on a literature review a significant number of articles have been published on Isoprothiolane.

Structure

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

HMDB0031779
     RDKit          3D
Isoprothiolane
 36 36  0  0  0  0  0  0  0  0999 V2000
   -3.9452   -1.1608    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9086   -1.2245   -0.5886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5541   -1.0702   -1.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9798   -0.1966   -0.3726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6439   -0.5103   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3183   -1.7317   -0.1994 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292    0.5356    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7168    0.1713    0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5963    1.0765    0.4521 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1346   -1.1429    0.2368 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5050   -1.4097    0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6613   -2.3350    1.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974   -2.1048   -0.7895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208    1.7859    0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9782    3.2419    0.3258 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3184    4.4358    0.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3883    4.2092   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771    2.4075   -0.1588 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4717   -1.5803    1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1826   -0.0987    0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8491   -1.7389    0.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4431   -2.2356   -0.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4081   -0.3583   -1.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9159   -2.0215   -2.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7701   -0.6633   -2.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0704   -0.4931    0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5274   -2.0039    2.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7300   -2.3511    2.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545   -3.3484    1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9158   -2.7766   -0.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572   -1.3661   -1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -2.7171   -1.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0575    5.4532    0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6914    4.0686    1.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436    4.7027    0.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0640    4.5509   -1.1846 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
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  7 14  2  3
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
 11 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
M  END

  Mrv0541 05061306072D          

 18 18  0  0  0  0            999 V2000
    3.4256    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2901    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5757    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  4  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 12  9  2  0  0  0  0
 13 10  2  0  0  0  0
 14 11  2  0  0  0  0
 15  7  1  0  0  0  0
 15 10  1  0  0  0  0
 16  8  1  0  0  0  0
 16 11  1  0  0  0  0
 17  5  1  0  0  0  0
 17 12  1  0  0  0  0
 18  6  1  0  0  0  0
 18 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031779

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1

> <INCHI_IDENTIFIER>
InChI=1S/C12H18O4S2/c1-7(2)15-10(13)9(11(14)16-8(3)4)12-17-5-6-18-12/h7-8H,5-6H2,1-4H3

> <INCHI_KEY>
UFHLMYOGRXOCSL-UHFFFAOYSA-N

> <FORMULA>
C12H18O4S2

> <MOLECULAR_WEIGHT>
290.399

> <EXACT_MASS>
290.064650444

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.315366865823524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-bis(propan-2-yl) 2-(1,3-dithiolan-2-ylidene)propanedioate

> <ALOGPS_LOGP>
3.15

> <JCHEM_LOGP>
3.223231548666666

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.973314248348526

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
84.4883

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
fuji 1

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031779
     RDKit          3D
Isoprothiolane
 36 36  0  0  0  0  0  0  0  0999 V2000
   -3.9452   -1.1608    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9086   -1.2245   -0.5886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5541   -1.0702   -1.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9798   -0.1966   -0.3726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6439   -0.5103   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3183   -1.7317   -0.1994 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292    0.5356    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7168    0.1713    0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5963    1.0765    0.4521 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1346   -1.1429    0.2368 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5050   -1.4097    0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6613   -2.3350    1.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974   -2.1048   -0.7895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208    1.7859    0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9782    3.2419    0.3258 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3184    4.4358    0.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3883    4.2092   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771    2.4075   -0.1588 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4717   -1.5803    1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1826   -0.0987    0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8491   -1.7389    0.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4431   -2.2356   -0.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4081   -0.3583   -1.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9159   -2.0215   -2.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7701   -0.6633   -2.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0704   -0.4931    0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5274   -2.0039    2.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7300   -2.3511    2.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545   -3.3484    1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9158   -2.7766   -0.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572   -1.3661   -1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -2.7171   -1.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0575    5.4532    0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6914    4.0686    1.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436    4.7027    0.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0640    4.5509   -1.1846 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
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  7 14  2  3
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
 11 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.394   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.061   5.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.275   3.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.941   5.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.061   4.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.941   4.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.393   5.930   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.274   5.930   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.727   3.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.608   3.620   0.000  0.00  0.00           O+0
HETATM   17  S   UNK     0      -0.186   1.175   0.000  0.00  0.00           S+0
HETATM   18  S   UNK     0       2.306   1.175   0.000  0.00  0.00           S+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4    8                                                            
CONECT    5    6   17                                                       
CONECT    6    5   18                                                       
CONECT    7    1    2   15                                                  
CONECT    8    3    4   16                                                  
CONECT    9   10   11   12                                                  
CONECT   10    9   13   15                                                  
CONECT   11    9   14   16                                                  
CONECT   12    9   17   18                                                  
CONECT   13   10                                                            
CONECT   14   11                                                            
CONECT   15    7   10                                                       
CONECT   16    8   11                                                       
CONECT   17    5   12                                                       
CONECT   18    6   12                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0031779
HETATM    1  C1  UNL     1      -3.945  -1.161   0.514  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.909  -1.224  -0.589  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.554  -1.070  -1.952  1.00  0.00           C  
HETATM    4  O1  UNL     1      -1.980  -0.197  -0.373  1.00  0.00           O  
HETATM    5  C4  UNL     1      -0.644  -0.510  -0.175  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.318  -1.732  -0.199  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.329   0.536   0.049  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.717   0.171   0.252  1.00  0.00           C  
HETATM    9  O3  UNL     1       2.596   1.077   0.452  1.00  0.00           O  
HETATM   10  O4  UNL     1       2.135  -1.143   0.237  1.00  0.00           O  
HETATM   11  C7  UNL     1       3.505  -1.410   0.443  1.00  0.00           C  
HETATM   12  C8  UNL     1       3.661  -2.335   1.651  1.00  0.00           C  
HETATM   13  C9  UNL     1       4.097  -2.105  -0.790  1.00  0.00           C  
HETATM   14  C10 UNL     1      -0.021   1.786   0.071  1.00  0.00           C  
HETATM   15  S1  UNL     1       0.978   3.242   0.326  1.00  0.00           S  
HETATM   16  C11 UNL     1      -0.318   4.436   0.841  1.00  0.00           C  
HETATM   17  C12 UNL     1      -1.388   4.209  -0.184  1.00  0.00           C  
HETATM   18  S2  UNL     1      -1.677   2.407  -0.159  1.00  0.00           S  
HETATM   19  H1  UNL     1      -3.472  -1.580   1.426  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.183  -0.099   0.736  1.00  0.00           H  
HETATM   21  H3  UNL     1      -4.849  -1.739   0.250  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.443  -2.236  -0.577  1.00  0.00           H  
HETATM   23  H5  UNL     1      -4.408  -0.358  -1.936  1.00  0.00           H  
HETATM   24  H6  UNL     1      -3.916  -2.021  -2.360  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.770  -0.663  -2.637  1.00  0.00           H  
HETATM   26  H8  UNL     1       4.070  -0.493   0.593  1.00  0.00           H  
HETATM   27  H9  UNL     1       4.527  -2.004   2.281  1.00  0.00           H  
HETATM   28  H10 UNL     1       2.730  -2.351   2.238  1.00  0.00           H  
HETATM   29  H11 UNL     1       3.854  -3.348   1.282  1.00  0.00           H  
HETATM   30  H12 UNL     1       4.916  -2.777  -0.526  1.00  0.00           H  
HETATM   31  H13 UNL     1       4.457  -1.366  -1.527  1.00  0.00           H  
HETATM   32  H14 UNL     1       3.262  -2.717  -1.216  1.00  0.00           H  
HETATM   33  H15 UNL     1       0.057   5.453   0.855  1.00  0.00           H  
HETATM   34  H16 UNL     1      -0.691   4.069   1.814  1.00  0.00           H  
HETATM   35  H17 UNL     1      -2.344   4.703   0.071  1.00  0.00           H  
HETATM   36  H18 UNL     1      -1.064   4.551  -1.185  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4   22
CONECT    3   23   24   25
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8   14   14
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   13   26
CONECT   12   27   28   29
CONECT   13   30   31   32
CONECT   14   15   18
CONECT   15   16
CONECT   16   17   33   34
CONECT   17   18   35   36
END

HMDB0031779
     RDKit          3D
Isoprothiolane
 36 36  0  0  0  0  0  0  0  0999 V2000
   -3.9452   -1.1608    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9086   -1.2245   -0.5886 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5541   -1.0702   -1.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9798   -0.1966   -0.3726 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6439   -0.5103   -0.1752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3183   -1.7317   -0.1994 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3292    0.5356    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7168    0.1713    0.2519 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5963    1.0765    0.4521 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1346   -1.1429    0.2368 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5050   -1.4097    0.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6613   -2.3350    1.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974   -2.1048   -0.7895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208    1.7859    0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9782    3.2419    0.3258 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3184    4.4358    0.8411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3883    4.2092   -0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6771    2.4075   -0.1588 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4717   -1.5803    1.4260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1826   -0.0987    0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8491   -1.7389    0.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4431   -2.2356   -0.5768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4081   -0.3583   -1.9359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9159   -2.0215   -2.3599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7701   -0.6633   -2.6372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0704   -0.4931    0.5927 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5274   -2.0039    2.2815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7300   -2.3511    2.2377 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545   -3.3484    1.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9158   -2.7766   -0.5264 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572   -1.3661   -1.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -2.7171   -1.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0575    5.4532    0.8554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6914    4.0686    1.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436    4.7027    0.0714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0640    4.5509   -1.1846 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
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  7 14  2  3
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 14  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
 11 26  1  0
 12 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 17 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Bis(1-methylethyl) 1,3-dithiolan-2-ylidenepropanedioate	ChEBI
Di-isopropyl 1,3-dithiolane-2-ylidenemalonate	ChEBI
Diisopropyl 1,3-dithiolan-2-ylidenemalonate	ChEBI
Diisopropyl 2-(1,3-dithiolan-2-ylidene)malonate	ChEBI
Bis(1-methylethyl) 1,3-dithiolan-2-ylidenepropanedioic acid	Generator
Di-isopropyl 1,3-dithiolane-2-ylidenemalonic acid	Generator
Diisopropyl 1,3-dithiolan-2-ylidenemalonic acid	Generator
Diisopropyl 2-(1,3-dithiolan-2-ylidene)malonic acid	Generator
Bis(1-methylethyl) 1,3-dithiolan-2-ylidenepropanedioate, 9ci	HMDB
Di(propan-2-yl) 1,3-dithiolan-2-ylidenemalonate	HMDB
Fudiolan	HMDB
Fuji 1	HMDB
Fuji-one	HMDB
Fujione	HMDB
IPT	HMDB
Ipt (pesticide)	HMDB
Fudzivan	HMDB

Chemical Formula

C₁₂H₁₈O₄S₂

Average Molecular Weight

290.399

Monoisotopic Molecular Weight

290.064650444

IUPAC Name

1,3-bis(propan-2-yl) 2-(1,3-dithiolan-2-ylidene)propanedioate

Traditional Name

fuji 1

CAS Registry Number

50512-35-1

SMILES

CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1

InChI Identifier

InChI=1S/C12H18O4S2/c1-7(2)15-10(13)9(11(14)16-8(3)4)12-17-5-6-18-12/h7-8H,5-6H2,1-4H3

InChI Key

UFHLMYOGRXOCSL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Dicarboxylic acids and derivatives

Direct Parent

Dicarboxylic acids and derivatives

Alternative Parents

Substituents

Vinylogous thioester
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,3-dithiolane
Dithiolane
Ketene acetal or derivatives
Carboxylic acid ester
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dithiolanes (CHEBI:6047 )
malonate ester (CHEBI:6047 )
Pesticides (C11111 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031779)
Cell membrane (HMDB: HMDB0031779)

Source

Endogenous

Endogenous (HMDB: HMDB0031779)

Exogenous

Food

Food (HMDB: HMDB0031779)

Exogenous (HMDB: HMDB0031779)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	50 - 54.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.054 mg/mL at 25 °C	Not Available
LogP	2.88	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.094 g/L	ALOGPS
logP	3.15	ALOGPS
logP	3.22	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.49 m³·mol⁻¹	ChemAxon
Polarizability	30.32 Å³	ChemAxon
Number of Rings	1	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
DarkChem	[M+H]+	168.122	31661259
DarkChem	[M-H]-	163.416	31661259
DeepCCS	[M+H]+	165.046	30932474
DeepCCS	[M-H]-	162.688	30932474
DeepCCS	[M-2H]-	195.942	30932474
DeepCCS	[M+Na]+	171.169	30932474
AllCCS	[M+H]+	161.1	32859911
AllCCS	[M+H-H2O]+	158.2	32859911
AllCCS	[M+NH4]+	163.8	32859911
AllCCS	[M+Na]+	164.5	32859911
AllCCS	[M-H]-	162.6	32859911
AllCCS	[M+Na-2H]-	163.3	32859911
AllCCS	[M+HCOO]-	164.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoprothiolane	CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1	2806.3	Standard polar	33892256
Isoprothiolane	CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1	1878.2	Standard non polar	33892256
Isoprothiolane	CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1	2045.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Isoprothiolane EI-B (Non-derivatized)	splash10-0j4u-2940000000-f1f31a9094505265794f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isoprothiolane EI-B (Non-derivatized)	splash10-02tc-0930000000-5238473738390cc4bf87	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isoprothiolane GC-EI-Q (Non-derivatized)	splash10-0296-4920000000-ec852d179ec53ec1212d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isoprothiolane EI-B (Non-derivatized)	splash10-0j4u-2940000000-f1f31a9094505265794f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isoprothiolane EI-B (Non-derivatized)	splash10-02tc-0930000000-5238473738390cc4bf87	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Isoprothiolane GC-EI-Q (Non-derivatized)	splash10-0296-4920000000-ec852d179ec53ec1212d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoprothiolane GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9140000000-c178fb571fef19f87028	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoprothiolane 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Isoprothiolane ESI-ITFT , positive-QTOF	splash10-001i-0190000000-345caa519a04634a9337	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprothiolane 10V, Positive-QTOF	splash10-0f6x-0290000000-0468aaa03d9f58afcaa1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprothiolane 20V, Positive-QTOF	splash10-0002-1790000000-f97fa47f0e03fe03bfe0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprothiolane 40V, Positive-QTOF	splash10-01ox-4900000000-38d7d4d29a66f23c0809	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprothiolane 10V, Negative-QTOF	splash10-01t9-4090000000-47113c3ac2f91e7303cf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprothiolane 20V, Negative-QTOF	splash10-0a6r-9110000000-b54910a7baf30f8ebb74	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprothiolane 40V, Negative-QTOF	splash10-0a4r-9510000000-fafd6cb3be3d814d69bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprothiolane 10V, Negative-QTOF	splash10-000i-0090000000-35f58dc5419431f0748e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprothiolane 20V, Negative-QTOF	splash10-052u-5390000000-5ce99d3498d8a406e265	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprothiolane 40V, Negative-QTOF	splash10-08fu-9500000000-603ade292dbdc56287a6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprothiolane 10V, Positive-QTOF	splash10-001l-0190000000-ecab00264edcd43adef4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprothiolane 20V, Positive-QTOF	splash10-000i-0900000000-5b1e7c50db7dfe241484	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoprothiolane 40V, Positive-QTOF	splash10-08g3-6920000000-28257315687afa95b9c0	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB008452

KNApSAcK ID

Not Available

Chemspider ID

36283

KEGG Compound ID

C11111

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

39681

PDB ID

Not Available

ChEBI ID

6047

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Isoprothiolane (HMDB0031779)

MOL for HMDB0031779 (Isoprothiolane)

3D MOL for HMDB0031779 (Isoprothiolane)

3D SDF for HMDB0031779 (Isoprothiolane)

3D-SDF for HMDB0031779 (Isoprothiolane)

PDB for HMDB0031779 (Isoprothiolane)

3D PDB for HMDB0031779 (Isoprothiolane)

SMILES for HMDB0031779 (Isoprothiolane)

INCHI for HMDB0031779 (Isoprothiolane)

Structure for HMDB0031779 (Isoprothiolane)

3D Structure for HMDB0031779 (Isoprothiolane)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra