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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:46:44 UTC

Update Date

2022-03-07 02:55:46 UTC

HMDB ID

HMDB0038459

Secondary Accession Numbers

HMDB38459

Metabolite Identification

Common Name

5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene

Description

5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene belongs to the class of organic compounds known as bi- and oligothiophenes. These are organic compounds containing two or more linked thiophene rings. Thiophene is a five-member aromatic ring with one sulfur and four carbon atoms. Based on a literature review very few articles have been published on 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene.

Structure

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

HMDB0038459
     RDKit          3D
5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene
 29 30  0  0  0  0  0  0  0  0999 V2000
    7.7745   -0.1180    0.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3858    0.2465    0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1864    1.1969    1.3357 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -0.3743    0.0028 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9819    0.0301    0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555   -0.7892   -0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3544   -1.6952   -1.1118 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5476   -0.5801   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658   -0.3885   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0686   -0.1623    0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7185    0.3079    1.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0575    0.4432    1.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6416    0.0944   -0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0899    0.1587   -0.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6934   -0.1854   -1.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0247   -0.0476   -1.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6709    0.4234   -0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3946    0.6599    0.6217 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3277   -0.4038   -0.9848 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8697   -1.2265    0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1535    0.3736   -0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4542    0.1491    1.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8714   -0.1614    1.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8161    1.1187    0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1512    0.5670    2.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6904    0.8191    2.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0851   -0.5638   -2.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6272   -0.2934   -2.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7520    0.6022   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  3  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 19  1  0
 19 10  1  0
 18 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  5 24  1  0
 11 25  1  0
 12 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
M  END


  Mrv0541 05061310282D          

 19 20  0  0  0  0            999 V2000
   -0.6126    1.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9595    2.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1526    2.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1849    1.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8994    2.3567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7001    3.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5071    3.7612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0458    3.2380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7560    1.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3271    1.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4705    1.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6139    2.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7401    2.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9196    3.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3271    2.7692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4705    0.7067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0415    1.5317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2921    3.5736    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3676    2.4337    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  5  4  3  0  0  0  0
  7  6  1  0  0  0  0
  8  2  2  0  0  0  0
 10  1  1  0  0  0  0
 11  4  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  1  0  0  0  0
 12  6  2  0  0  0  0
 13  3  2  0  0  0  0
 14  7  2  0  0  0  0
 14 13  1  0  0  0  0
 15 10  2  0  0  0  0
 16 11  2  0  0  0  0
 17  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18  8  1  0  0  0  0
 18 13  1  0  0  0  0
 19 12  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038459

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OCC(=O)C#CC1=CC=C(S1)C1=CC=CS1

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O3S2/c1-10(15)17-9-11(16)4-5-12-6-7-14(19-12)13-3-2-8-18-13/h2-3,6-8H,9H2,1H3

> <INCHI_KEY>
DTTMMEKKOHDZHY-UHFFFAOYSA-N

> <FORMULA>
C14H10O3S2

> <MOLECULAR_WEIGHT>
290.357

> <EXACT_MASS>
290.007135566

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.141713568595854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-oxo-4-[5-(thiophen-2-yl)thiophen-2-yl]but-3-yn-1-yl acetate

> <ALOGPS_LOGP>
3.35

> <JCHEM_LOGP>
3.439667547333333

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.0965473318785

> <JCHEM_PKA_STRONGEST_BASIC>
-6.947974802231669

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
71.55319999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-oxo-4-[5-(thiophen-2-yl)thiophen-2-yl]but-3-yn-1-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038459
     RDKit          3D
5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene
 29 30  0  0  0  0  0  0  0  0999 V2000
    7.7745   -0.1180    0.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3858    0.2465    0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1864    1.1969    1.3357 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -0.3743    0.0028 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9819    0.0301    0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555   -0.7892   -0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3544   -1.6952   -1.1118 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5476   -0.5801   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658   -0.3885   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0686   -0.1623    0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7185    0.3079    1.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0575    0.4432    1.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6416    0.0944   -0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0899    0.1587   -0.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6934   -0.1854   -1.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0247   -0.0476   -1.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6709    0.4234   -0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3946    0.6599    0.6217 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3277   -0.4038   -0.9848 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8697   -1.2265    0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1535    0.3736   -0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4542    0.1491    1.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8714   -0.1614    1.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8161    1.1187    0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1512    0.5670    2.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6904    0.8191    2.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0851   -0.5638   -2.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6272   -0.2934   -2.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7520    0.6022   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  3  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 19  1  0
 19 10  1  0
 18 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  5 24  1  0
 11 25  1  0
 12 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  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      -1.144   2.859   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -16.724   4.513   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -15.218   4.193   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.812   3.629   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.146   4.399   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.640   6.701   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -12.147   7.021   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -16.885   6.044   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.145   3.629   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.477   3.629   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -6.478   2.859   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.479   5.169   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -14.448   5.526   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -12.917   5.687   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.477   5.169   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -6.478   1.319   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -3.811   2.859   0.000  0.00  0.00           O+0
HETATM   18  S   UNK     0     -15.479   6.671   0.000  0.00  0.00           S+0
HETATM   19  S   UNK     0     -11.886   4.543   0.000  0.00  0.00           S+0
CONECT    1   10                                                            
CONECT    2    3    8                                                       
CONECT    3    2   13                                                       
CONECT    4    5   11                                                       
CONECT    5    4   12                                                       
CONECT    6    7   12                                                       
CONECT    7    6   14                                                       
CONECT    8    2   18                                                       
CONECT    9   11   17                                                       
CONECT   10    1   15   17                                                  
CONECT   11    4    9   16                                                  
CONECT   12    5    6   19                                                  
CONECT   13    3   14   18                                                  
CONECT   14    7   13   19                                                  
CONECT   15   10                                                            
CONECT   16   11                                                            
CONECT   17    9   10                                                       
CONECT   18    8   13                                                       
CONECT   19   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0038459
HETATM    1  C1  UNL     1       7.774  -0.118   0.209  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.386   0.247   0.526  1.00  0.00           C  
HETATM    3  O1  UNL     1       6.186   1.197   1.336  1.00  0.00           O  
HETATM    4  O2  UNL     1       5.277  -0.374   0.003  1.00  0.00           O  
HETATM    5  C3  UNL     1       3.982   0.030   0.353  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.956  -0.789  -0.339  1.00  0.00           C  
HETATM    7  O3  UNL     1       3.354  -1.695  -1.112  1.00  0.00           O  
HETATM    8  C5  UNL     1       1.548  -0.580  -0.155  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.366  -0.388  -0.014  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.069  -0.162   0.132  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.718   0.308   1.237  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.058   0.443   1.159  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.642   0.094  -0.029  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.090   0.159  -0.346  1.00  0.00           C  
HETATM   15  C12 UNL     1      -5.693  -0.185  -1.526  1.00  0.00           C  
HETATM   16  C13 UNL     1      -7.025  -0.048  -1.595  1.00  0.00           C  
HETATM   17  C14 UNL     1      -7.671   0.423  -0.486  1.00  0.00           C  
HETATM   18  S1  UNL     1      -6.395   0.660   0.622  1.00  0.00           S  
HETATM   19  S2  UNL     1      -2.328  -0.404  -0.985  1.00  0.00           S  
HETATM   20  H1  UNL     1       7.870  -1.226   0.079  1.00  0.00           H  
HETATM   21  H2  UNL     1       8.154   0.374  -0.716  1.00  0.00           H  
HETATM   22  H3  UNL     1       8.454   0.149   1.046  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.871  -0.161   1.456  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.816   1.119   0.214  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.151   0.567   2.165  1.00  0.00           H  
HETATM   26  H7  UNL     1      -3.690   0.819   2.003  1.00  0.00           H  
HETATM   27  H8  UNL     1      -5.085  -0.564  -2.386  1.00  0.00           H  
HETATM   28  H9  UNL     1      -7.627  -0.293  -2.498  1.00  0.00           H  
HETATM   29  H10 UNL     1      -8.752   0.602  -0.353  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   23   24
CONECT    6    7    7    8
CONECT    8    9    9    9
CONECT    9   10
CONECT   10   11   11   19
CONECT   11   12   25
CONECT   12   13   13   26
CONECT   13   14   19
CONECT   14   15   15   18
CONECT   15   16   27
CONECT   16   17   17   28
CONECT   17   18   29
END

HMDB0038459
     RDKit          3D
5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene
 29 30  0  0  0  0  0  0  0  0999 V2000
    7.7745   -0.1180    0.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3858    0.2465    0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1864    1.1969    1.3357 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -0.3743    0.0028 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9819    0.0301    0.3531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9555   -0.7892   -0.3393 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3544   -1.6952   -1.1118 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5476   -0.5801   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3658   -0.3885   -0.0138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0686   -0.1623    0.1318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7185    0.3079    1.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0575    0.4432    1.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6416    0.0944   -0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0899    0.1587   -0.3456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6934   -0.1854   -1.5263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0247   -0.0476   -1.5952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6709    0.4234   -0.4863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3946    0.6599    0.6217 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3277   -0.4038   -0.9848 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.8697   -1.2265    0.0786 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1535    0.3736   -0.7163 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4542    0.1491    1.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8714   -0.1614    1.4560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8161    1.1187    0.2143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1512    0.5670    2.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6904    0.8191    2.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0851   -0.5638   -2.3861 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6272   -0.2934   -2.4975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7520    0.6022   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  3  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 13 19  1  0
 19 10  1  0
 18 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  5 24  1  0
 11 25  1  0
 12 26  1  0
 15 27  1  0
 16 28  1  0
 17 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
TPL	HMDB
Triptolid	HMDB
Triptolide	HMDB
Triptolide (9ci)	HMDB
Triptolide, tripterygium wilfordii	HMDB
4-{[2,2'-bithiophene]-5-yl}-2-oxobut-3-yn-1-yl acetic acid	Generator

Chemical Formula

C₁₄H₁₀O₃S₂

Average Molecular Weight

290.357

Monoisotopic Molecular Weight

290.007135566

IUPAC Name

2-oxo-4-[5-(thiophen-2-yl)thiophen-2-yl]but-3-yn-1-yl acetate

Traditional Name

2-oxo-4-[5-(thiophen-2-yl)thiophen-2-yl]but-3-yn-1-yl acetate

CAS Registry Number

1222-83-9

SMILES

CC(=O)OCC(=O)C#CC1=CC=C(S1)C1=CC=CS1

InChI Identifier

InChI=1S/C14H10O3S2/c1-10(15)17-9-11(16)4-5-12-6-7-14(19-12)13-3-2-8-18-13/h2-3,6-8H,9H2,1H3

InChI Key

DTTMMEKKOHDZHY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bi- and oligothiophenes. These are organic compounds containing two or more linked thiophene rings. Thiophene is a five-member aromatic ring with one sulfur and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Bi- and oligothiophenes

Sub Class

Not Available

Direct Parent

Bi- and oligothiophenes

Alternative Parents

Substituents

Bithiophene
2,5-disubstituted thiophene
Alpha-acyloxy ketone
Thiophene
Alpha,beta-unsaturated ketone
Heteroaromatic compound
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038459)

Membrane (HMDB: HMDB0038459)
Cell membrane (HMDB: HMDB0038459)

Source

Exogenous

Food

Food (HMDB: HMDB0038459)

Not Available

Nutrient (HMDB: HMDB0038459)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	68 °C	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	0.02 g/L	ALOGPS
logP	3.35	ALOGPS
logP	3.44	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	17.1	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	71.55 m³·mol⁻¹	ChemAxon
Polarizability	30.14 Å³	ChemAxon
Number of Rings	2	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]+	167.856	31661259
DarkChem	[M-H]-	167.054	31661259
DeepCCS	[M+H]+	155.229	30932474
DeepCCS	[M-H]-	152.871	30932474
DeepCCS	[M-2H]-	186.628	30932474
DeepCCS	[M+Na]+	161.68	30932474
AllCCS	[M+H]+	162.3	32859911
AllCCS	[M+H-H2O]+	158.8	32859911
AllCCS	[M+NH4]+	165.6	32859911
AllCCS	[M+Na]+	166.6	32859911
AllCCS	[M-H]-	164.9	32859911
AllCCS	[M+Na-2H]-	164.7	32859911
AllCCS	[M+HCOO]-	164.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene	CC(=O)OCC(=O)C#CC1=CC=C(S1)C1=CC=CS1	3670.8	Standard polar	33892256
5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene	CC(=O)OCC(=O)C#CC1=CC=C(S1)C1=CC=CS1	2429.2	Standard non polar	33892256
5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene	CC(=O)OCC(=O)C#CC1=CC=C(S1)C1=CC=CS1	2528.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene,1TMS,isomer #1	CC(=O)OC=C(C#CC1=CC=C(C2=CC=CS2)S1)O[Si](C)(C)C	2661.6	Semi standard non polar	33892256
5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene,1TMS,isomer #1	CC(=O)OC=C(C#CC1=CC=C(C2=CC=CS2)S1)O[Si](C)(C)C	2545.8	Standard non polar	33892256
5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene,1TBDMS,isomer #1	CC(=O)OC=C(C#CC1=CC=C(C2=CC=CS2)S1)O[Si](C)(C)C(C)(C)C	2880.2	Semi standard non polar	33892256
5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene,1TBDMS,isomer #1	CC(=O)OC=C(C#CC1=CC=C(C2=CC=CS2)S1)O[Si](C)(C)C(C)(C)C	2796.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-6390000000-a703e07ce2d493a7135a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene 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 - 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene 10V, Positive-QTOF	splash10-006x-0090000000-9f1d31b78d9dfae649cf	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene 20V, Positive-QTOF	splash10-006x-1190000000-33a952358358fc1a70ec	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene 40V, Positive-QTOF	splash10-0006-7390000000-8f5c11eb1f9d42ae34db	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene 10V, Negative-QTOF	splash10-000i-2090000000-6ab1c097b48779266178	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene 20V, Negative-QTOF	splash10-000i-4190000000-4614b7d2689a676cd581	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene 40V, Negative-QTOF	splash10-052f-9110000000-522751047a26b6cd87fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene 10V, Positive-QTOF	splash10-001l-0090000000-5f5852d5f92ee139c640	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene 20V, Positive-QTOF	splash10-000t-0090000000-143f367ae50bbb655886	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene 40V, Positive-QTOF	splash10-000l-1910000000-7f7f59c52ce6c0ce717c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene 10V, Negative-QTOF	splash10-000i-0090000000-ab243076771e8e2ae4e7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene 20V, Negative-QTOF	splash10-000i-0190000000-9d97d8fdeca74c0ea874	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene 40V, Negative-QTOF	splash10-03dr-0920000000-f96718b4fc62d8b6dcad	2021-09-22	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

FDB017818

KNApSAcK ID

C00054207

Chemspider ID

30777254

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752377

PDB ID

Not Available

ChEBI ID

169239

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 5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene (HMDB0038459)

MOL for HMDB0038459 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

3D MOL for HMDB0038459 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

3D SDF for HMDB0038459 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

3D-SDF for HMDB0038459 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

PDB for HMDB0038459 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

3D PDB for HMDB0038459 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

SMILES for HMDB0038459 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

INCHI for HMDB0038459 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

Structure for HMDB0038459 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

3D Structure for HMDB0038459 (5-(4-Acetoxy-3-oxo-1-butynyl)-2,2'-bithiophene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra