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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

Cell membrane (HMDB: HMDB0034454)

Cellular substructure

Membrane (HMDB: HMDB0034454)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034454)

Source

Exogenous

Food

Food (HMDB: HMDB0034454)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0034454)

Not Available

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 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

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9230000000-554b2fbe8c3c6cedd8bd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(4-Acetoxy-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-1-butynyl)-2,2'-bithiophene 10V, Positive-QTOF	splash10-00or-1090000000-cdc8c3dbbc7d5b917129	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 20V, Positive-QTOF	splash10-014i-3690000000-83993ad838519da6972b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 40V, Positive-QTOF	splash10-00l6-9520000000-b3a5619ce781b4bfb35b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 10V, Negative-QTOF	splash10-004i-4190000000-ce9b14e688d25f54633b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 20V, Negative-QTOF	splash10-0a4i-9130000000-50b68e71c9ad3db4f15b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 40V, Negative-QTOF	splash10-0a4l-9200000000-b8979ecd0ba33b4f511f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 10V, Positive-QTOF	splash10-00or-0090000000-72e87881f01aad83c636	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 20V, Positive-QTOF	splash10-001i-0090000000-460a71401789276498a7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 40V, Positive-QTOF	splash10-0f77-0930000000-2afc7e22a584cd5e504c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 10V, Negative-QTOF	splash10-004i-1090000000-5993b5eb3c52930c57d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 20V, Negative-QTOF	splash10-0udi-0090000000-b80b91c07d0f1b7f348c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(4-Acetoxy-1-butynyl)-2,2'-bithiophene 40V, Negative-QTOF	splash10-0udi-1590000000-3573fc31cccca9dd5557	2021-09-24	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

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 Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra