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Showing metabocard for Benzothiophene (HMDB0249003)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 03:28:00 UTC
Update Date2021-09-26 22:59:36 UTC
HMDB IDHMDB0249003
Secondary Accession NumbersNone
Metabolite Identification
Common NameBenzothiophene
Description1-benzothiophene, also known as thianaphthene or 1-thiaindene, belongs to the class of organic compounds known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system. Based on a literature review a significant number of articles have been published on 1-benzothiophene. This compound has been identified in human blood as reported by (PMID: 31557052 ). Benzothiophene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Benzothiophene is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0249003 (Benzothiophene)

  Mrv1533004251508052D          

  9 10  0  0  0  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  1  9  1  0  0  0  0
M  END
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3D MOL for HMDB0249003 (Benzothiophene)

HMDB0249003
     RDKit          3D
Benzothiophene
 15 16  0  0  0  0  0  0  0  0999 V2000
   -1.7770   -0.8489   -0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1853    0.4311   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1825    1.3512    0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1633    0.9492    0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6354    1.7651    0.4941 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7184    0.4666    0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8842   -0.5832    0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5638   -0.3332   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4814   -1.2434   -0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5691   -1.5746   -0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2243    0.6836   -0.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4134    2.3796    0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8240    0.4379    0.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344   -1.5905   -0.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2905   -2.2906   -0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  1  1  0
  8  4  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  6 13  1  0
  7 14  1  0
  9 15  1  0
M  END
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3D SDF for HMDB0249003 (Benzothiophene)

  Mrv1533004251508052D          

  9 10  0  0  0  0            999 V2000
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  1  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249003

> <DATABASE_NAME>
hmdb

> <SMILES>
S1C=CC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C8H6S/c1-2-4-8-7(3-1)5-6-9-8/h1-6H

> <INCHI_KEY>
FCEHBMOGCRZNNI-UHFFFAOYSA-N

> <FORMULA>
C8H6S

> <MOLECULAR_WEIGHT>
134.2

> <EXACT_MASS>
134.019021367

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
14.22673767840022

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-benzothiophene

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
2.849270612333333

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
39.3981

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzothiophene

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0249003 (Benzothiophene)

HMDB0249003
     RDKit          3D
Benzothiophene
 15 16  0  0  0  0  0  0  0  0999 V2000
   -1.7770   -0.8489   -0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1853    0.4311   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1825    1.3512    0.2104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1633    0.9492    0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6354    1.7651    0.4941 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.7184    0.4666    0.2882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8842   -0.5832    0.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5638   -0.3332   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4814   -1.2434   -0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5691   -1.5746   -0.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2243    0.6836   -0.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4134    2.3796    0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8240    0.4379    0.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3344   -1.5905   -0.1828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2905   -2.2906   -0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  1  1  0
  8  4  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  6 13  1  0
  7 14  1  0
  9 15  1  0
M  END
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PDB for HMDB0249003 (Benzothiophene)

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0       2.126   1.597   0.000  0.00  0.00           S+0
HETATM    6  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    4    9                                                  
CONECT    9    8    1                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   20    0
END
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3D PDB for HMDB0249003 (Benzothiophene)

COMPND    HMDB0249003
HETATM    1  C1  UNL     1      -1.777  -0.849  -0.306  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.185   0.431  -0.057  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.182   1.351   0.210  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.163   0.949   0.216  1.00  0.00           C  
HETATM    5  S1  UNL     1       1.635   1.765   0.494  1.00  0.00           S  
HETATM    6  C5  UNL     1       2.718   0.467   0.288  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.884  -0.583   0.004  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.564  -0.333  -0.033  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.481  -1.243  -0.302  1.00  0.00           C  
HETATM   10  H1  UNL     1      -2.569  -1.575  -0.517  1.00  0.00           H  
HETATM   11  H2  UNL     1      -3.224   0.684  -0.075  1.00  0.00           H  
HETATM   12  H3  UNL     1      -1.413   2.380   0.417  1.00  0.00           H  
HETATM   13  H4  UNL     1       3.824   0.438   0.358  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.334  -1.590  -0.183  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.290  -2.291  -0.515  1.00  0.00           H  
CONECT    1    2    2    9   10
CONECT    2    3   11
CONECT    3    4    4   12
CONECT    4    5    8
CONECT    5    6
CONECT    6    7    7   13
CONECT    7    8   14
CONECT    8    9    9
CONECT    9   15
END
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SMILES for HMDB0249003 (Benzothiophene)

S1C=CC2=CC=CC=C12
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INCHI for HMDB0249003 (Benzothiophene)

InChI=1S/C8H6S/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1-ThiaindeneChEBI
Benzo[b]thiopheneChEBI
BenzothiofuranChEBI
ThianaphtheneChEBI
Benzo(b)thiopheneMeSH
BenzothiopheneMeSH
Chemical FormulaC8H6S
Average Molecular Weight134.2
Monoisotopic Molecular Weight134.019021367
IUPAC Name1-benzothiophene
Traditional Namebenzothiophene
CAS Registry NumberNot Available
SMILES
S1C=CC2=CC=CC=C12
InChI Identifier
InChI=1S/C8H6S/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
InChI KeyFCEHBMOGCRZNNI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-benzothiophenes. These are aromatic heterocyclic compound containing the Benzo[b]thiophene ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiophenes
Sub Class1-benzothiophenes
Direct Parent1-benzothiophenes
Alternative Parents
Substituents
  • 1-benzothiophene
  • Benzenoid
  • Heteroaromatic compound
  • Thiophene
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP3.24ALOGPS
logP2.85ChemAxon
logS-2.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.4 m³·mol⁻¹ChemAxon
Polarizability14.23 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6951
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzothiophene
METLIN IDNot Available
PubChem Compound7221
PDB IDNot Available
ChEBI ID35858
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1578681
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]