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Showing metabocard for 2-Acetylthiophene (HMDB0033133)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:53:55 UTC
Update Date2023-02-21 17:23:07 UTC
HMDB IDHMDB0033133
Secondary Accession Numbers
  • HMDB33133
Metabolite Identification
Common Name2-Acetylthiophene
Description2-Acetylthiophene, also known as 2-acetothienone or thiophene,2-acetyl, belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group. 2-Acetylthiophene is a sulfury tasting compound. 2-Acetylthiophene is found, on average, in the highest concentration within kohlrabis. 2-Acetylthiophene has also been detected, but not quantified, in asparagus. This could make 2-acetylthiophene a potential biomarker for the consumption of these foods.
Structure
Data?1677000187
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0033133 (2-Acetylthiophene)


  Mrv1652305261923532D          

  8  8  0  0  0  0            999 V2000
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  2  0  0  0  0
  5  1  1  0  0  0  0
  6  3  2  0  0  0  0
  6  5  1  0  0  0  0
  7  5  2  0  0  0  0
  8  4  1  0  0  0  0
  8  6  1  0  0  0  0
M  END
Download

3D MOL for HMDB0033133 (2-Acetylthiophene)

HMDB0033133
     RDKit          3D
2-Acetylthiophene
 14 14  0  0  0  0  0  0  0  0999 V2000
   -2.3406   -0.1180    0.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3275    0.8271   -0.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6925    1.8913   -1.0171 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0978    0.4969   -0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6535   -0.6060    0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9948   -0.6802    0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6963    0.3495   -0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4569    1.3948   -0.7932 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9664   -1.1403    0.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1872   -0.1745   -0.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7248    0.2098    1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0129   -1.3852    0.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -1.5289    0.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7971    0.4636   -0.3283 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  4  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
M  END
Download

3D SDF for HMDB0033133 (2-Acetylthiophene)


  Mrv1652305261923532D          

  8  8  0  0  0  0            999 V2000
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  2  0  0  0  0
  5  1  1  0  0  0  0
  6  3  2  0  0  0  0
  6  5  1  0  0  0  0
  7  5  2  0  0  0  0
  8  4  1  0  0  0  0
  8  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033133

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)C1=CC=CS1

> <INCHI_IDENTIFIER>
InChI=1S/C6H6OS/c1-5(7)6-3-2-4-8-6/h2-4H,1H3

> <INCHI_KEY>
WYJOVVXUZNRJQY-UHFFFAOYSA-N

> <FORMULA>
C6H6OS

> <MOLECULAR_WEIGHT>
126.176

> <EXACT_MASS>
126.013935504

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
14

> <JCHEM_AVERAGE_POLARIZABILITY>
12.717966707681217

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-(thiophen-2-yl)ethan-1-one

> <ALOGPS_LOGP>
1.28

> <JCHEM_LOGP>
1.4437747076666667

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.958114479013645

> <JCHEM_PKA_STRONGEST_BASIC>
-7.809546142304336

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
33.3507

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-acetylthiophene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0033133 (2-Acetylthiophene)

HMDB0033133
     RDKit          3D
2-Acetylthiophene
 14 14  0  0  0  0  0  0  0  0999 V2000
   -2.3406   -0.1180    0.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3275    0.8271   -0.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6925    1.8913   -1.0171 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0978    0.4969   -0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6535   -0.6060    0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9948   -0.6802    0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6963    0.3495   -0.2537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4569    1.3948   -0.7932 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9664   -1.1403    0.1648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1872   -0.1745   -0.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7248    0.2098    1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0129   -1.3852    0.7021 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5553   -1.5289    0.7459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7971    0.4636   -0.3283 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  4  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
M  END
Download

PDB for HMDB0033133 (2-Acetylthiophene)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.393   4.390   0.000  0.00  0.00           O+0
HETATM    8  S   UNK     0      -0.186   1.175   0.000  0.00  0.00           S+0
CONECT    1    5                                                            
CONECT    2    3    4                                                       
CONECT    3    2    6                                                       
CONECT    4    2    8                                                       
CONECT    5    1    6    7                                                  
CONECT    6    3    5    8                                                  
CONECT    7    5                                                            
CONECT    8    4    6                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for HMDB0033133 (2-Acetylthiophene)

COMPND    HMDB0033133
HETATM    1  C1  UNL     1      -2.341  -0.118   0.059  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.328   0.827  -0.456  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.693   1.891  -1.017  1.00  0.00           O  
HETATM    4  C3  UNL     1       0.098   0.497  -0.299  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.654  -0.606   0.280  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.995  -0.680   0.302  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.696   0.349  -0.254  1.00  0.00           C  
HETATM    8  S1  UNL     1       1.457   1.395  -0.793  1.00  0.00           S  
HETATM    9  H1  UNL     1      -1.966  -1.140   0.165  1.00  0.00           H  
HETATM   10  H2  UNL     1      -3.187  -0.174  -0.682  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.725   0.210   1.068  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.013  -1.385   0.702  1.00  0.00           H  
HETATM   13  H5  UNL     1       2.555  -1.529   0.746  1.00  0.00           H  
HETATM   14  H6  UNL     1       3.797   0.464  -0.328  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    4
CONECT    4    5    5    8
CONECT    5    6   12
CONECT    6    7    7   13
CONECT    7    8   14
END
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SMILES for HMDB0033133 (2-Acetylthiophene)

CC(=O)C1=CC=CS1
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INCHI for HMDB0033133 (2-Acetylthiophene)

InChI=1S/C6H6OS/c1-5(7)6-3-2-4-8-6/h2-4H,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1-(2-Thienyl)-ethanoneHMDB
1-(2-Thienyl)ethanoneHMDB
1-(2-Thienyl)ethanone, 9ciHMDB
1-Thiophen-2-yl-ethanoneHMDB
2-AcethylthiopheneHMDB
2-AcetothienoneHMDB
2-AcetothiopheneHMDB
2-AcetylthiophenHMDB
2-Thienyl methyl ketoneHMDB
alpha-AcetylthiopheneHMDB
Ketone, methyl 2-thienylHMDB
Methyl 2-thienyl ketoneHMDB
Methyl-2-thienyl ketoneHMDB
THIOPHENE,2-acetylHMDB
2-AcetylthiopheneMeSH
Chemical FormulaC6H6OS
Average Molecular Weight126.176
Monoisotopic Molecular Weight126.013935504
IUPAC Name1-(thiophen-2-yl)ethan-1-one
Traditional Name2-acetylthiophene
CAS Registry Number88-15-3
SMILES
CC(=O)C1=CC=CS1
InChI Identifier
InChI=1S/C6H6OS/c1-5(7)6-3-2-4-8-6/h2-4H,1H3
InChI KeyWYJOVVXUZNRJQY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryl alkyl ketones. These are ketones have the generic structure RC(=O)R', where R = aryl group and R'=alkyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl alkyl ketones
Alternative Parents
Substituents
  • Aryl alkyl ketone
  • Heteroaromatic compound
  • Thiophene
  • Organoheterocyclic compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point9 °CNot Available
Boiling Point213.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility14 mg/mL at 30 °CNot Available
LogP1.25Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.91 g/LALOGPS
logP1.28ALOGPS
logP1.44ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)14.96ChemAxon
pKa (Strongest Basic)-7.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.35 m³·mol⁻¹ChemAxon
Polarizability12.72 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.65631661259
DarkChem[M-H]-118.78531661259
DeepCCS[M+H]+127.80230932474
DeepCCS[M-H]-125.71930932474
DeepCCS[M-2H]-161.30430932474
DeepCCS[M+Na]+135.67930932474
AllCCS[M+H]+122.432859911
AllCCS[M+H-H2O]+117.632859911
AllCCS[M+NH4]+127.032859911
AllCCS[M+Na]+128.332859911
AllCCS[M-H]-123.932859911
AllCCS[M+Na-2H]-126.332859911
AllCCS[M+HCOO]-129.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-AcetylthiopheneCC(=O)C1=CC=CS11733.2Standard polar33892256
2-AcetylthiopheneCC(=O)C1=CC=CS11033.6Standard non polar33892256
2-AcetylthiopheneCC(=O)C1=CC=CS11078.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Acetylthiophene EI-B (Non-derivatized)splash10-03fr-3900000000-f96bcae1b452aa83d4c82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Acetylthiophene EI-B (Non-derivatized)splash10-03di-7900000000-857b33ff69870de2f3402017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Acetylthiophene EI-B (Non-derivatized)splash10-03fr-3900000000-f96bcae1b452aa83d4c82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Acetylthiophene EI-B (Non-derivatized)splash10-03di-7900000000-857b33ff69870de2f3402018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Acetylthiophene GC-MS (Non-derivatized) - 70eV, Positivesplash10-06vu-9400000000-51103572f0e23662b98b2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Acetylthiophene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Acetylthiophene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylthiophene 10V, Positive-QTOFsplash10-056r-0900000000-2f4fa00685ac1768a3572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylthiophene 20V, Positive-QTOFsplash10-004i-0900000000-e07fd7b790d62f487ffd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylthiophene 40V, Positive-QTOFsplash10-0a4i-4900000000-c401ba1f2ff8b40736a02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylthiophene 10V, Negative-QTOFsplash10-004i-0900000000-a22e2fdb212f2aae61db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylthiophene 20V, Negative-QTOFsplash10-0059-5900000000-66a4340e769e9d088d0f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylthiophene 40V, Negative-QTOFsplash10-0a4i-9000000000-c7e99f903fd6cdfa6f182016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylthiophene 10V, Negative-QTOFsplash10-001i-9100000000-7543ad714c7071e1a7252021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylthiophene 20V, Negative-QTOFsplash10-001i-9000000000-7d99ce9954aa98dbedf62021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylthiophene 40V, Negative-QTOFsplash10-0a4i-9000000000-aa4ca3b62a339ccc651a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylthiophene 10V, Positive-QTOFsplash10-004l-6900000000-d9c3fc40dd5da9ccf9eb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylthiophene 20V, Positive-QTOFsplash10-0006-9100000000-00c18beba67e86df50e22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Acetylthiophene 40V, Positive-QTOFsplash10-0006-9000000000-9a655bce1c1c041d1dd72021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011134
KNApSAcK IDC00054096
Chemspider ID6654
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6920
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1038531
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .