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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:07:35 UTC

Update Date

2021-09-14 15:15:58 UTC

HMDB ID

HMDB0060925

Secondary Accession Numbers

HMDB60925

Metabolite Identification

Common Name

Thiophene-4,5-epoxide

Description

Thiophene-4,5-epoxide belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. Thiophene-4,5-epoxide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0060925
     RDKit          3D
Thiophene-4,5-epoxide
 31 33  0  0  0  0  0  0  0  0999 V2000
   -3.7736    0.7417   -1.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4154    0.0180   -0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8924    0.7854    1.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1874    1.1550    2.0969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2345    1.1396    1.1644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9769   -0.3053    0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5377   -1.6087    0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061   -1.9090    0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7997   -0.9092    0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1790   -1.2984    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786   -2.5899    0.2081 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3562   -0.5057    0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7185    0.7348    0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1105    1.0125    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1061    1.2705   -0.4825 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6439    0.0954   -0.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0566   -1.3219    0.1843 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3477    0.3799    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0219    0.6736    0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5950    0.2359   -1.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9069    0.7954   -2.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1621    1.7737   -1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9769   -0.9381   -0.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9103    0.5068    1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2875   -2.4180    0.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1454   -2.9321    0.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760    1.5599    0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5146    0.8511    1.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1208    0.0883   -1.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013    1.2115    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3704    1.7072    0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  9 18  1  0
 18 19  2  0
 19  6  1  0
 17 12  1  0
 16 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
 18 30  1  0
 19 31  1  0
M  END


  Mrv0541 07091309072D          

 19 21  0  0  0  0            999 V2000
    6.0275   -2.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9650   -2.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7900   -0.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5525   -1.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425    0.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025   -2.9191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7900   -2.2046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9650   -0.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275   -0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5525   -0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7900   -3.6336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579   -0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9650    0.6533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2025   -4.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9650   -3.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434   -0.0612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425   -0.7286    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  7  1  1  0  0  0  0
  8  2  2  0  0  0  0
  8  3  1  0  0  0  0
  8  7  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  6  2  0  0  0  0
 12  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 14 10  1  0  0  0  0
 15 12  2  0  0  0  0
 16 13  2  0  0  0  0
 17 13  1  0  0  0  0
 18 10  1  0  0  0  0
 18 14  1  0  0  0  0
 19 11  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060925

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C(O)=O)C1=CC=C(C=C1)C(=O)C1=CC2OC2S1

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O4S/c1-7(13(16)17)8-2-4-9(5-3-8)12(15)11-6-10-14(18-10)19-11/h2-7,10,14H,1H3,(H,16,17)

> <INCHI_KEY>
SDGBIPHZPNRUFG-UHFFFAOYSA-N

> <FORMULA>
C14H12O4S

> <MOLECULAR_WEIGHT>
276.308

> <EXACT_MASS>
276.045629562

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.578904520375275

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-{6-oxa-2-thiabicyclo[3.1.0]hex-3-ene-3-carbonyl}phenyl)propanoic acid

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
2.2533335303333337

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7385692214789996

> <JCHEM_PKA_STRONGEST_BASIC>
-4.313427558431402

> <JCHEM_POLAR_SURFACE_AREA>
66.9

> <JCHEM_REFRACTIVITY>
72.64620000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-{6-oxa-2-thiabicyclo[3.1.0]hex-3-ene-3-carbonyl}phenyl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060925
     RDKit          3D
Thiophene-4,5-epoxide
 31 33  0  0  0  0  0  0  0  0999 V2000
   -3.7736    0.7417   -1.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4154    0.0180   -0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8924    0.7854    1.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1874    1.1550    2.0969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2345    1.1396    1.1644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9769   -0.3053    0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5377   -1.6087    0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061   -1.9090    0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7997   -0.9092    0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1790   -1.2984    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786   -2.5899    0.2081 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3562   -0.5057    0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7185    0.7348    0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1105    1.0125    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1061    1.2705   -0.4825 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6439    0.0954   -0.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0566   -1.3219    0.1843 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3477    0.3799    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0219    0.6736    0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5950    0.2359   -1.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9069    0.7954   -2.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1621    1.7737   -1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9769   -0.9381   -0.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9103    0.5068    1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2875   -2.4180    0.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1454   -2.9321    0.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760    1.5599    0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5146    0.8511    1.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1208    0.0883   -1.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013    1.2115    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3704    1.7072    0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  9 18  1  0
 18 19  2  0
 19  6  1  0
 17 12  1  0
 16 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
 18 30  1  0
 19 31  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0      11.251  -5.449   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.711  -2.782   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.401  -4.115   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.941  -1.448   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.631  -2.782   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.186   1.132   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.711  -5.449   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.941  -4.115   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.401  -1.448   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.721   0.656   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.091  -0.114   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.631  -0.114   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.941  -6.783   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.721  -0.884   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.401   1.219   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.711  -8.116   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.401  -6.783   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.388  -0.114   0.000  0.00  0.00           O+0
HETATM   19  S   UNK     0       4.186  -1.360   0.000  0.00  0.00           S+0
CONECT    1    7                                                            
CONECT    2    4    8                                                       
CONECT    3    5    8                                                       
CONECT    4    2    9                                                       
CONECT    5    3    9                                                       
CONECT    6   10   11                                                       
CONECT    7    1    8   13                                                  
CONECT    8    2    3    7                                                  
CONECT    9    4    5   12                                                  
CONECT   10    6   14   18                                                  
CONECT   11    6   12   19                                                  
CONECT   12    9   11   15                                                  
CONECT   13    7   16   17                                                  
CONECT   14   10   18   19                                                  
CONECT   15   12                                                            
CONECT   16   13                                                            
CONECT   17   13                                                            
CONECT   18   10   14                                                       
CONECT   19   11   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0060925
HETATM    1  C1  UNL     1      -3.774   0.742  -1.327  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.415   0.018  -0.031  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.892   0.785   1.126  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.187   1.155   2.097  1.00  0.00           O  
HETATM    5  O2  UNL     1      -5.235   1.140   1.164  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.977  -0.305   0.028  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.538  -1.609   0.051  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.206  -1.909   0.106  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.800  -0.909   0.142  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.179  -1.298   0.198  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.379  -2.590   0.208  1.00  0.00           O  
HETATM   12  C9  UNL     1       3.356  -0.506   0.242  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.719   0.735   0.257  1.00  0.00           C  
HETATM   14  C11 UNL     1       5.111   1.013   0.317  1.00  0.00           C  
HETATM   15  O4  UNL     1       6.106   1.271  -0.483  1.00  0.00           O  
HETATM   16  C12 UNL     1       5.644   0.095  -0.788  1.00  0.00           C  
HETATM   17  S1  UNL     1       5.057  -1.322   0.184  1.00  0.00           S  
HETATM   18  C13 UNL     1       0.348   0.380   0.119  1.00  0.00           C  
HETATM   19  C14 UNL     1      -1.022   0.674   0.063  1.00  0.00           C  
HETATM   20  H1  UNL     1      -4.595   0.236  -1.872  1.00  0.00           H  
HETATM   21  H2  UNL     1      -2.907   0.795  -2.004  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.162   1.774  -1.100  1.00  0.00           H  
HETATM   23  H4  UNL     1      -3.977  -0.938  -0.051  1.00  0.00           H  
HETATM   24  H5  UNL     1      -5.910   0.507   1.572  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.287  -2.418   0.024  1.00  0.00           H  
HETATM   26  H7  UNL     1       0.145  -2.932   0.124  1.00  0.00           H  
HETATM   27  H8  UNL     1       2.976   1.560   0.224  1.00  0.00           H  
HETATM   28  H9  UNL     1       5.515   0.851   1.375  1.00  0.00           H  
HETATM   29  H10 UNL     1       5.121   0.088  -1.770  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.001   1.211   0.142  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.370   1.707   0.045  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    6   23
CONECT    3    4    4    5
CONECT    5   24
CONECT    6    7    7   19
CONECT    7    8   25
CONECT    8    9    9   26
CONECT    9   10   18
CONECT   10   11   11   12
CONECT   12   13   13   17
CONECT   13   14   27
CONECT   14   15   16   28
CONECT   15   16
CONECT   16   17   29
CONECT   18   19   19   30
CONECT   19   31
END

HMDB0060925
     RDKit          3D
Thiophene-4,5-epoxide
 31 33  0  0  0  0  0  0  0  0999 V2000
   -3.7736    0.7417   -1.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4154    0.0180   -0.0315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8924    0.7854    1.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1874    1.1550    2.0969 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2345    1.1396    1.1644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9769   -0.3053    0.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5377   -1.6087    0.0508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2061   -1.9090    0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7997   -0.9092    0.1424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1790   -1.2984    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786   -2.5899    0.2081 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3562   -0.5057    0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7185    0.7348    0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1105    1.0125    0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1061    1.2705   -0.4825 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6439    0.0954   -0.7883 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0566   -1.3219    0.1843 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3477    0.3799    0.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0219    0.6736    0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5950    0.2359   -1.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9069    0.7954   -2.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1621    1.7737   -1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9769   -0.9381   -0.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9103    0.5068    1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2875   -2.4180    0.0236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1454   -2.9321    0.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9760    1.5599    0.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5146    0.8511    1.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1208    0.0883   -1.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013    1.2115    0.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3704    1.7072    0.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  9 18  1  0
 18 19  2  0
 19  6  1  0
 17 12  1  0
 16 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  5 24  1  0
  7 25  1  0
  8 26  1  0
 13 27  1  0
 14 28  1  0
 16 29  1  0
 18 30  1  0
 19 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₁₂O₄S

Average Molecular Weight

276.308

Monoisotopic Molecular Weight

276.045629562

IUPAC Name

2-(4-{6-oxa-2-thiabicyclo[3.1.0]hex-3-ene-3-carbonyl}phenyl)propanoic acid

Traditional Name

2-(4-{6-oxa-2-thiabicyclo[3.1.0]hex-3-ene-3-carbonyl}phenyl)propanoic acid

CAS Registry Number

Not Available

SMILES

CC(C(O)=O)C1=CC=C(C=C1)C(=O)C1=CC2OC2S1

InChI Identifier

InChI=1S/C14H12O4S/c1-7(13(16)17)8-2-4-9(5-3-8)12(15)11-6-10-14(18-10)19-11/h2-7,10,14H,1H3,(H,16,17)

InChI Key

SDGBIPHZPNRUFG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

2-phenylpropanoic-acid
P-cymene
Aromatic monoterpenoid
Bicyclic monoterpenoid
Monoterpenoid
Benzoyl
Aryl ketone
Monocyclic benzene moiety
1,3-oxathiin
Benzenoid
Monothioacetal
2,3-dihydrothiophene
Ketone
Thioenolether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxirane
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060925)

Organ

Kidney (HMDB: HMDB0060925)
Liver (HMDB: HMDB0060925)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060925)

Cellular substructure

Cytoplasm (HMDB: HMDB0060925)
Membrane (HMDB: HMDB0060925)

Source

Endogenous

Endogenous (HMDB: HMDB0060925)

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
Water Solubility	0.1 g/L	ALOGPS
logP	2.06	ALOGPS
logP	2.25	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	3.74	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	72.65 m³·mol⁻¹	ChemAxon
Polarizability	27.58 Å³	ChemAxon
Number of Rings	3	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]+	163.491	31661259
DarkChem	[M-H]-	161.718	31661259
DeepCCS	[M+H]+	158.523	30932474
DeepCCS	[M-H]-	156.127	30932474
DeepCCS	[M-2H]-	189.078	30932474
DeepCCS	[M+Na]+	164.536	30932474
AllCCS	[M+H]+	162.5	32859911
AllCCS	[M+H-H2O]+	158.8	32859911
AllCCS	[M+NH4]+	165.9	32859911
AllCCS	[M+Na]+	166.9	32859911
AllCCS	[M-H]-	166.0	32859911
AllCCS	[M+Na-2H]-	165.6	32859911
AllCCS	[M+HCOO]-	165.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	5.91 minutes	32390414
Predicted by Siyang on May 30, 2022	15.023 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.11 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2126.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	431.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	163.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	250.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	146.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	612.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	694.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	142.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1237.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	496.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1480.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	417.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	426.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	543.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	396.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	137.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Thiophene-4,5-epoxide	CC(C(O)=O)C1=CC=C(C=C1)C(=O)C1=CC2OC2S1	3688.3	Standard polar	33892256
Thiophene-4,5-epoxide	CC(C(O)=O)C1=CC=C(C=C1)C(=O)C1=CC2OC2S1	2256.2	Standard non polar	33892256
Thiophene-4,5-epoxide	CC(C(O)=O)C1=CC=C(C=C1)C(=O)C1=CC2OC2S1	2516.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Thiophene-4,5-epoxide,1TMS,isomer #1	CC(C(=O)O[Si](C)(C)C)C1=CC=C(C(=O)C2=CC3OC3S2)C=C1	2549.3	Semi standard non polar	33892256
Thiophene-4,5-epoxide,1TBDMS,isomer #1	CC(C(=O)O[Si](C)(C)C(C)(C)C)C1=CC=C(C(=O)C2=CC3OC3S2)C=C1	2795.5	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 - Thiophene-4,5-epoxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-2920000000-651ad0632600c8035bd0	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiophene-4,5-epoxide GC-MS (1 TMS) - 70eV, Positive	splash10-05as-8940000000-fceeb260ec5f1c655fa8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiophene-4,5-epoxide 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 - Thiophene-4,5-epoxide 10V, Positive-QTOF	splash10-056r-0090000000-32b4a891609cea10d363	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiophene-4,5-epoxide 20V, Positive-QTOF	splash10-0560-0970000000-0c0dc73782a74a74e675	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiophene-4,5-epoxide 40V, Positive-QTOF	splash10-0faa-2920000000-439543c83056f195aba0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiophene-4,5-epoxide 10V, Negative-QTOF	splash10-004i-0090000000-34806146aed16dcb566d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiophene-4,5-epoxide 20V, Negative-QTOF	splash10-017j-7090000000-2e47f6d313092f513460	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiophene-4,5-epoxide 40V, Negative-QTOF	splash10-009j-6910000000-c08934a60d8e9a94182b	2017-10-06	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131769994

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 Thiophene-4,5-epoxide (HMDB0060925)

MOL for HMDB0060925 (Thiophene-4,5-epoxide)

3D MOL for HMDB0060925 (Thiophene-4,5-epoxide)

3D SDF for HMDB0060925 (Thiophene-4,5-epoxide)

3D-SDF for HMDB0060925 (Thiophene-4,5-epoxide)

PDB for HMDB0060925 (Thiophene-4,5-epoxide)

3D PDB for HMDB0060925 (Thiophene-4,5-epoxide)

SMILES for HMDB0060925 (Thiophene-4,5-epoxide)

INCHI for HMDB0060925 (Thiophene-4,5-epoxide)

Structure for HMDB0060925 (Thiophene-4,5-epoxide)

3D Structure for HMDB0060925 (Thiophene-4,5-epoxide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra