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Showing metabocard for Benzofuran (HMDB0032929)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:52:43 UTC
Update Date2023-02-21 17:22:48 UTC
HMDB IDHMDB0032929
Secondary Accession Numbers
  • HMDB32929
Metabolite Identification
Common NameBenzofuran
DescriptionBenzofuran, also known as coumaron or 1-oxaindene, belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Benzothiophene, an analog with a sulfur instead of the oxygen atom. Benzofuran is a drug. benzofuran has been detected, but not quantified, in several different foods, such as alcoholic beverages, coffee and coffee products, herbs and spices, root vegetables, and tea. This could make benzofuran a potential biomarker for the consumption of these foods. This colourless liquid is a component of coal tar. Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. Benzofuran is a potentially toxic compound. For example, psoralen is a benzofuran derivative that occurs in several plants. Isobenzofuran, the isomer with oxygen in the adjacent position.
Structure
Data?1677000168
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032929 (Benzofuran)


  Mrv1652305271900032D          

  9 10  0  0  0  0            999 V2000
   -0.1435   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  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
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
M  END
Download

3D MOL for HMDB0032929 (Benzofuran)

HMDB0032929
     RDKit          3D
Benzofuran
 15 16  0  0  0  0  0  0  0  0999 V2000
   -1.9332    0.5871    0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9891   -0.7600   -0.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7980   -1.4297   -0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4242   -0.7909   -0.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6759   -1.2107   -0.2549 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5389   -0.2752   -0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8185    0.8793    0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4830    0.5547    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147    1.2192    0.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8666    1.1221    0.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9603   -1.2762   -0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8158   -2.5010   -0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6198   -0.2811   -0.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1816    1.8784    0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6641    2.2839    0.4767 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
Download

3D SDF for HMDB0032929 (Benzofuran)


  Mrv1652305271900032D          

  9 10  0  0  0  0            999 V2000
   -0.1435   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  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
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032929

> <DATABASE_NAME>
hmdb

> <SMILES>
O1C=CC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H

> <INCHI_KEY>
IANQTJSKSUMEQM-UHFFFAOYSA-N

> <FORMULA>
C8H6O

> <MOLECULAR_WEIGHT>
118.1326

> <EXACT_MASS>
118.041864814

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
12.33147517144278

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-benzofuran

> <ALOGPS_LOGP>
2.75

> <JCHEM_LOGP>
2.1323692166666666

> <ALOGPS_LOGS>
-2.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9157258827171466

> <JCHEM_POLAR_SURFACE_AREA>
13.14

> <JCHEM_REFRACTIVITY>
34.8991

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzofuran

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0032929 (Benzofuran)

HMDB0032929
     RDKit          3D
Benzofuran
 15 16  0  0  0  0  0  0  0  0999 V2000
   -1.9332    0.5871    0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9891   -0.7600   -0.1548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7980   -1.4297   -0.2963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4242   -0.7909   -0.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6759   -1.2107   -0.2549 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5389   -0.2752   -0.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8185    0.8793    0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4830    0.5547    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147    1.2192    0.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8666    1.1221    0.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9603   -1.2762   -0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8158   -2.5010   -0.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6198   -0.2811   -0.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1816    1.8784    0.3874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6641    2.2839    0.4767 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 HMDB0032929 (Benzofuran)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      -0.268  -0.057   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.268  -2.549   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   20    0
END
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3D PDB for HMDB0032929 (Benzofuran)

COMPND    HMDB0032929
HETATM    1  C1  UNL     1      -1.933   0.587   0.126  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.989  -0.760  -0.155  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.798  -1.430  -0.296  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.424  -0.791  -0.165  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.676  -1.211  -0.255  1.00  0.00           O  
HETATM    6  C5  UNL     1       2.539  -0.275  -0.062  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.819   0.879   0.180  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.483   0.555   0.115  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.715   1.219   0.255  1.00  0.00           C  
HETATM   10  H1  UNL     1      -2.867   1.122   0.238  1.00  0.00           H  
HETATM   11  H2  UNL     1      -2.960  -1.276  -0.261  1.00  0.00           H  
HETATM   12  H3  UNL     1      -0.816  -2.501  -0.519  1.00  0.00           H  
HETATM   13  H4  UNL     1       3.620  -0.281  -0.065  1.00  0.00           H  
HETATM   14  H5  UNL     1       2.182   1.878   0.387  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.664   2.284   0.477  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 HMDB0032929 (Benzofuran)

O1C=CC2=C1C=CC=C2
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INCHI for HMDB0032929 (Benzofuran)

InChI=1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Benzo[b]furanChEBI
CoumaronChEBI
CoumaroneChEBI
CumaroneChEBI
1-BenzofuranHMDB
1-OxaindeneHMDB
1-OxideneHMDB
1-OxindeneHMDB
2,3-BenzofuranHMDB, MeSH
benzo(b)FuranHMDB, MeSH
BenzofurfuranHMDB, MeSH
BZFHMDB
CumaronHMDB
BenzofuranChEBI
Chemical FormulaC8H6O
Average Molecular Weight118.1326
Monoisotopic Molecular Weight118.041864814
IUPAC Name1-benzofuran
Traditional Namebenzofuran
CAS Registry Number271-89-6
SMILES
O1C=CC2=C1C=CC=C2
InChI Identifier
InChI=1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
InChI KeyIANQTJSKSUMEQM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzofurans
Sub ClassNot Available
Direct ParentBenzofurans
Alternative Parents
Substituents
  • Benzofuran
  • Benzenoid
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point< -18 °CNot Available
Boiling Point174.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility534.8 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.67Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.82 g/LALOGPS
logP2.75ALOGPS
logP2.13ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area13.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.9 m³·mol⁻¹ChemAxon
Polarizability12.33 ųChemAxon
Number of Rings2ChemAxon
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]+121.03931661259
DarkChem[M-H]-118.38631661259
DeepCCS[M+H]+123.60330932474
DeepCCS[M-H]-120.70630932474
DeepCCS[M-2H]-157.41930932474
DeepCCS[M+Na]+132.23230932474
AllCCS[M+H]+121.232859911
AllCCS[M+H-H2O]+116.132859911
AllCCS[M+NH4]+126.032859911
AllCCS[M+Na]+127.432859911
AllCCS[M-H]-117.832859911
AllCCS[M+Na-2H]-119.232859911
AllCCS[M+HCOO]-120.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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. Predicted by Afia on May 17, 2022.4.0 minutes32390414
Predicted by Siyang on May 30, 202214.5191 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20224.4 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1878.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid589.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid237.1 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid400.5 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid289.7 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid528.2 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid636.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)291.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1208.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid473.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1247.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid426.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid417.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate568.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA429.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water93.6 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BenzofuranO1C=CC2=C1C=CC=C21511.3Standard polar33892256
BenzofuranO1C=CC2=C1C=CC=C21002.3Standard non polar33892256
BenzofuranO1C=CC2=C1C=CC=C21005.8Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Membrane
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 IDDB04179
Phenol Explorer Compound IDNot Available
FooDB IDFDB010914
KNApSAcK IDC00054105
Chemspider ID8868
KEGG Compound IDC14512
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link1-benzofuran
METLIN IDNot Available
PubChem Compound9223
PDB IDNot Available
ChEBI ID35260
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1161131
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Wahab Khan M, Jahangir Alam M, Rashid MA, Chowdhury R: A new structural alternative in benzo[b]furans for antimicrobial activity. Bioorg Med Chem. 2005 Aug 15;13(16):4796-805. [PubMed:15964760 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .