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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:17:52 UTC

Update Date

2022-03-07 02:54:06 UTC

HMDB ID

HMDB0034454

Secondary Accession Numbers

HMDB34454

Metabolite Identification

Common Name

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

Description

5-(4-Acetoxy-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. Thus, 5-(4-acetoxy-1-butynyl)-2,2'-bithiophene is considered to be an oxygenated hydrocarbon. 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene has been detected, but not quantified in, herbs and spices. This could make 5-(4-acetoxy-1-butynyl)-2,2'-bithiophene a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene.

Structure

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

HMDB0034454
     RDKit          3D
5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene
 30 31  0  0  0  0  0  0  0  0999 V2000
    7.3212    0.5119    0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8480    0.3664    0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3296   -0.3290    1.6627 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0722    1.0121   -0.1633 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6740    0.9578   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1620   -0.4627   -0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7069   -0.4695   -0.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4942   -0.4682   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9540   -0.4792   -0.4896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7775   -1.0069   -1.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1081   -0.8842   -1.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5135   -0.2491   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8929    0.0234    0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0822   -0.3001   -0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1994    0.0654    0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0686    0.7287    1.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3721    0.8239    1.7755 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0449    0.1651    0.6463 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7041   -0.1945   -0.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8090    0.2724    1.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6026    1.5476    0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3448    1.5271   -1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2109    1.4124    0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455   -1.1239    0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5207   -0.7680   -1.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3165   -1.5068   -2.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8475   -1.2857   -1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0792   -0.8461   -1.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2152   -0.1437    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8740    1.1035    2.2392 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  1  0
  7  8  3  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 18  1  0
 18  9  1  0
 17 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
 10 26  1  0
 11 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
M  END


  Mrv0541 05061307492D          

 18 19  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
   -4.1849    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
   -8.9595    2.4176    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
   -8.1526    2.2460    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
   -2.7560    1.9442    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
   -1.3271    1.9442    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
   -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  2  3  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 11  1  1  0  0  0  0
 12  5  1  0  0  0  0
 12  7  2  0  0  0  0
 13  6  2  0  0  0  0
 14  8  2  0  0  0  0
 14 13  1  0  0  0  0
 15 11  2  0  0  0  0
 16  9  1  0  0  0  0
 16 11  1  0  0  0  0
 17 10  1  0  0  0  0
 17 13  1  0  0  0  0
 18 12  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034454

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O2S2/c1-11(15)16-9-3-2-5-12-7-8-14(18-12)13-6-4-10-17-13/h4,6-8,10H,3,9H2,1H3

> <INCHI_KEY>
KHPAKGUGOFYJNA-UHFFFAOYSA-N

> <FORMULA>
C14H12O2S2

> <MOLECULAR_WEIGHT>
276.374

> <EXACT_MASS>
276.027871008

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
30.132654216023088

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.61

> <JCHEM_LOGP>
3.7434875199999995

> <ALOGPS_LOGS>
-4.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.976341584319819

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
71.1124

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.02e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0034454
     RDKit          3D
5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene
 30 31  0  0  0  0  0  0  0  0999 V2000
    7.3212    0.5119    0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8480    0.3664    0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3296   -0.3290    1.6627 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0722    1.0121   -0.1633 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6740    0.9578   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1620   -0.4627   -0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7069   -0.4695   -0.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4942   -0.4682   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9540   -0.4792   -0.4896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7775   -1.0069   -1.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1081   -0.8842   -1.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5135   -0.2491   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8929    0.0234    0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0822   -0.3001   -0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1994    0.0654    0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0686    0.7287    1.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3721    0.8239    1.7755 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0449    0.1651    0.6463 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7041   -0.1945   -0.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8090    0.2724    1.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6026    1.5476    0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3448    1.5271   -1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2109    1.4124    0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455   -1.1239    0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5207   -0.7680   -1.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3165   -1.5068   -2.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8475   -1.2857   -1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0792   -0.8461   -1.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2152   -0.1437    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8740    1.1035    2.2392 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  1  0
  7  8  3  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 18  1  0
 18  9  1  0
 17 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
 10 26  1  0
 11 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  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      -7.812   3.629   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.478   2.859   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -16.724   4.513   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     -15.218   4.193   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.640   6.701   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -12.147   7.021   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     -16.885   6.044   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.477   3.629   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      -3.811   2.859   0.000  0.00  0.00           O+0
HETATM   17  S   UNK     0     -15.479   6.671   0.000  0.00  0.00           S+0
HETATM   18  S   UNK     0     -11.886   4.543   0.000  0.00  0.00           S+0
CONECT    1   11                                                            
CONECT    2    3    5                                                       
CONECT    3    2    9                                                       
CONECT    4    6   10                                                       
CONECT    5    2   12                                                       
CONECT    6    4   13                                                       
CONECT    7    8   12                                                       
CONECT    8    7   14                                                       
CONECT    9    3   16                                                       
CONECT   10    4   17                                                       
CONECT   11    1   15   16                                                  
CONECT   12    5    7   18                                                  
CONECT   13    6   14   17                                                  
CONECT   14    8   13   18                                                  
CONECT   15   11                                                            
CONECT   16    9   11                                                       
CONECT   17   10   13                                                       
CONECT   18   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0034454
HETATM    1  C1  UNL     1       7.321   0.512   0.699  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.848   0.366   0.771  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.330  -0.329   1.663  1.00  0.00           O  
HETATM    4  O2  UNL     1       5.072   1.012  -0.163  1.00  0.00           O  
HETATM    5  C3  UNL     1       3.674   0.958  -0.208  1.00  0.00           C  
HETATM    6  C4  UNL     1       3.162  -0.463  -0.392  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.707  -0.469  -0.434  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.494  -0.468  -0.449  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.954  -0.479  -0.490  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.778  -1.007  -1.445  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.108  -0.884  -1.245  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.513  -0.249  -0.115  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.893   0.023   0.352  1.00  0.00           C  
HETATM   14  C12 UNL     1      -6.082  -0.300  -0.244  1.00  0.00           C  
HETATM   15  C13 UNL     1      -7.199   0.065   0.394  1.00  0.00           C  
HETATM   16  C14 UNL     1      -7.069   0.729   1.581  1.00  0.00           C  
HETATM   17  S1  UNL     1      -5.372   0.824   1.776  1.00  0.00           S  
HETATM   18  S2  UNL     1      -2.045   0.165   0.646  1.00  0.00           S  
HETATM   19  H1  UNL     1       7.704  -0.195  -0.056  1.00  0.00           H  
HETATM   20  H2  UNL     1       7.809   0.272   1.680  1.00  0.00           H  
HETATM   21  H3  UNL     1       7.603   1.548   0.421  1.00  0.00           H  
HETATM   22  H4  UNL     1       3.345   1.527  -1.114  1.00  0.00           H  
HETATM   23  H5  UNL     1       3.211   1.412   0.701  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.546  -1.124   0.388  1.00  0.00           H  
HETATM   25  H7  UNL     1       3.521  -0.768  -1.420  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.317  -1.507  -2.331  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.847  -1.286  -1.973  1.00  0.00           H  
HETATM   28  H10 UNL     1      -6.079  -0.846  -1.219  1.00  0.00           H  
HETATM   29  H11 UNL     1      -8.215  -0.144   0.005  1.00  0.00           H  
HETATM   30  H12 UNL     1      -7.874   1.103   2.239  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   22   23
CONECT    6    7   24   25
CONECT    7    8    8    8
CONECT    8    9
CONECT    9   10   10   18
CONECT   10   11   26
CONECT   11   12   12   27
CONECT   12   13   18
CONECT   13   14   14   17
CONECT   14   15   28
CONECT   15   16   16   29
CONECT   16   17   30
END

HMDB0034454
     RDKit          3D
5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene
 30 31  0  0  0  0  0  0  0  0999 V2000
    7.3212    0.5119    0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8480    0.3664    0.7707 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3296   -0.3290    1.6627 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0722    1.0121   -0.1633 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6740    0.9578   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1620   -0.4627   -0.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7069   -0.4695   -0.4337 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4942   -0.4682   -0.4490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9540   -0.4792   -0.4896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7775   -1.0069   -1.4447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1081   -0.8842   -1.2447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5135   -0.2491   -0.1153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8929    0.0234    0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0822   -0.3001   -0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1994    0.0654    0.3936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0686    0.7287    1.5810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3721    0.8239    1.7755 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0449    0.1651    0.6463 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7041   -0.1945   -0.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8090    0.2724    1.6802 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6026    1.5476    0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3448    1.5271   -1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2109    1.4124    0.7007 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455   -1.1239    0.3875 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5207   -0.7680   -1.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3165   -1.5068   -2.3315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8475   -1.2857   -1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0792   -0.8461   -1.2193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2152   -0.1437    0.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8740    1.1035    2.2392 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  1  0
  7  8  3  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 12 18  1  0
 18  9  1  0
 17 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
 10 26  1  0
 11 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(5-(2-Thienyl)-2-thienyl)-3-butyn-1-ol acetate	ChEBI
4-(5-(2-Thienyl)-2-thienyl)-3-butyn-1-ol acetic acid	Generator
3-Butyn-1-ol, 4-(5-(2-thienyl)-2-thienyl)-, acetate	HMDB
4-(2,2'-Bithien-5-yl)but-3-yn-1-yl acetate	HMDB
5-(4-Acetoxybut-1-ynyl)-2,2'-bithiophene	HMDB
5-(4-Acetoxybut-1-ynyl)-2-2'-bithiophene	HMDB
5-4-ACETOXYBUT-1-ynyl-2-2-bithiophene	HMDB
4-([2,2'-Bithiophen]-5-yl)but-3-yn-1-yl acetic acid	Generator

Chemical Formula

C₁₄H₁₂O₂S₂

Average Molecular Weight

276.374

Monoisotopic Molecular Weight

276.027871008

IUPAC Name

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

Traditional Name

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

CAS Registry Number

1219-28-9

SMILES

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

InChI Identifier

InChI=1S/C14H12O2S2/c1-11(15)16-9-3-2-5-12-7-8-14(18-12)13-6-4-10-17-13/h4,6-8,10H,3,9H2,1H3

InChI Key

KHPAKGUGOFYJNA-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
Heteroaromatic compound
Thiophene
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

2,2'-bithiophenes (CHEBI:17181 )
a small molecule (5-4-ACETOXYBUT-1-YNYL-2-2-BITHIOPHENE )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034454)
Cell membrane (HMDB: HMDB0034454)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034454)

Source

Exogenous

Exogenous (HMDB: HMDB0034454)

Food

Food (HMDB: HMDB0034454)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0034454)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034454)

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	4 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.02 g/L	ALOGPS
logP	4.61	ALOGPS
logP	3.74	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	71.11 m³·mol⁻¹	ChemAxon
Polarizability	30.13 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	164.349	31661259
DarkChem	[M-H]-	160.702	31661259
DeepCCS	[M+H]+	152.395	30932474
DeepCCS	[M-H]-	150.012	30932474
DeepCCS	[M-2H]-	184.021	30932474
DeepCCS	[M+Na]+	158.774	30932474
AllCCS	[M+H]+	159.9	32859911
AllCCS	[M+H-H2O]+	156.3	32859911
AllCCS	[M+NH4]+	163.3	32859911
AllCCS	[M+Na]+	164.3	32859911
AllCCS	[M-H]-	161.7	32859911
AllCCS	[M+Na-2H]-	161.5	32859911
AllCCS	[M+HCOO]-	161.4	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 × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	7.04 minutes	32390414
Predicted by Siyang on May 30, 2022	16.1786 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.91 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2308.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	522.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	201.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	311.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	339.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	649.4 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	619.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1436.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	497.9 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	1456.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	458.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	423.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	401.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	460.9 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	30.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene	CC(=O)OCCC#CC1=CC=C(S1)C1=CC=CS1	3234.6	Standard polar	33892256
5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene	CC(=O)OCCC#CC1=CC=C(S1)C1=CC=CS1	2336.6	Standard non polar	33892256
5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene	CC(=O)OCCC#CC1=CC=C(S1)C1=CC=CS1	2405.9	Semi standard non polar	33892256

Spectra

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

FDB012863

KNApSAcK ID

Not Available

Chemspider ID

389319

KEGG Compound ID

C04485

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440356

PDB ID

Not Available

ChEBI ID

17181

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1842961

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-1-butynyl)-2,2'-bithiophene (HMDB0034454)

MOL for HMDB0034454 (5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene)

3D MOL for HMDB0034454 (5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene)

3D SDF for HMDB0034454 (5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene)

3D-SDF for HMDB0034454 (5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene)

PDB for HMDB0034454 (5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene)

3D PDB for HMDB0034454 (5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene)

SMILES for HMDB0034454 (5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene)

INCHI for HMDB0034454 (5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene)

Structure for HMDB0034454 (5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene)

3D Structure for HMDB0034454 (5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized