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Showing metabocard for 2-Methylfuran (HMDB0013749)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-05-18 14:35:49 UTC
Update Date2023-02-21 17:18:02 UTC
HMDB IDHMDB0013749
Secondary Accession Numbers
  • HMDB13749
Metabolite Identification
Common Name2-Methylfuran
Description2-Methylfuran, also known as alpha-methylfuran or 2-MF, belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom. 2-Methylfuran is an acetone, chocolate, and ethereal tasting compound. 2-Methylfuran is found, on average, in the highest concentration within milk (cow). 2-Methylfuran has also been detected, but not quantified in, several different foods, such as blackberries (Rubus), cauliflowers (Brassica oleracea var. botrytis), evergreen blackberries (Rubus laciniatus), and tamarinds (Tamarindus indica). This could make 2-methylfuran a potential biomarker for the consumption of these foods. 2-Methylfuran is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 2-Methylfuran.
Structure
Data?1676999882
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0013749 (2-Methylfuran)


  Mrv1652303102016532D          

  6  6  0  0  0  0            999 V2000
   -0.2471    0.6600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2471   -0.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  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
  5  6  1  0  0  0  0
M  END
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3D MOL for HMDB0013749 (2-Methylfuran)

HMDB0013749
     RDKit          3D
2-Methylfuran
 12 12  0  0  0  0  0  0  0  0999 V2000
   -1.8767   -0.2856   -0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019   -0.1766   -0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3397    0.9699    0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6553    0.5815    0.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6604   -0.7900    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4257   -1.1794   -0.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2093   -0.7070   -1.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2896   -0.9394    0.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3384    0.7291   -0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0308    2.0062    0.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5195    1.2368    0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5460   -1.4454    0.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  2  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
M  END
Download

3D SDF for HMDB0013749 (2-Methylfuran)


  Mrv1652303102016532D          

  6  6  0  0  0  0            999 V2000
   -0.2471    0.6600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2471   -0.6600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  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
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013749

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=CO1

> <INCHI_IDENTIFIER>
InChI=1S/C5H6O/c1-5-3-2-4-6-5/h2-4H,1H3

> <INCHI_KEY>
VQKFNUFAXTZWDK-UHFFFAOYSA-N

> <FORMULA>
C5H6O

> <MOLECULAR_WEIGHT>
82.1005

> <EXACT_MASS>
82.041864814

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
8.847867297264314

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methylfuran

> <ALOGPS_LOGP>
1.75

> <JCHEM_LOGP>
1.3130526593333336

> <ALOGPS_LOGS>
-0.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7978732909896054

> <JCHEM_POLAR_SURFACE_AREA>
13.14

> <JCHEM_REFRACTIVITY>
23.7211

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
silvan

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0013749 (2-Methylfuran)

HMDB0013749
     RDKit          3D
2-Methylfuran
 12 12  0  0  0  0  0  0  0  0999 V2000
   -1.8767   -0.2856   -0.1625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019   -0.1766   -0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3397    0.9699    0.0797 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6553    0.5815    0.1565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6604   -0.7900    0.0758 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4257   -1.1794   -0.0408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2093   -0.7070   -1.1185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2896   -0.9394    0.6486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3384    0.7291   -0.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0308    2.0062    0.1128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5195    1.2368    0.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5460   -1.4454    0.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  2  1  0
  1  7  1  0
  1  8  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  5 12  1  0
M  END
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PDB for HMDB0013749 (2-Methylfuran)

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  O   UNK     0      -0.461   1.232   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.001   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.461  -1.232   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.461   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.001   0.000   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    1    4    6                                                  
CONECT    6    5                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   12    0
END
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3D PDB for HMDB0013749 (2-Methylfuran)

COMPND    HMDB0013749
HETATM    1  C1  UNL     1      -1.877  -0.286  -0.163  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.402  -0.177  -0.044  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.340   0.970   0.080  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.655   0.582   0.156  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.660  -0.790   0.076  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.426  -1.179  -0.041  1.00  0.00           O  
HETATM    7  H1  UNL     1      -2.209  -0.707  -1.118  1.00  0.00           H  
HETATM    8  H2  UNL     1      -2.290  -0.939   0.649  1.00  0.00           H  
HETATM    9  H3  UNL     1      -2.338   0.729  -0.072  1.00  0.00           H  
HETATM   10  H4  UNL     1      -0.031   2.006   0.113  1.00  0.00           H  
HETATM   11  H5  UNL     1       2.520   1.237   0.261  1.00  0.00           H  
HETATM   12  H6  UNL     1       2.546  -1.445   0.104  1.00  0.00           H  
CONECT    1    2    7    8    9
CONECT    2    3    3    6
CONECT    3    4   10
CONECT    4    5    5   11
CONECT    5    6   12
END
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SMILES for HMDB0013749 (2-Methylfuran)

CC1=CC=CO1
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INCHI for HMDB0013749 (2-Methylfuran)

InChI=1S/C5H6O/c1-5-3-2-4-6-5/h2-4H,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-Methyl furanChEBI
2-Methyl-furanChEBI
2-MethylfuraneChEBI
2-MFChEBI
5-MethylfuranChEBI
alpha-MethylfuranChEBI
SilvanChEBI
SylvanChEBI
a-MethylfuranGenerator
Α-methylfuranGenerator
2-Methylfuran (acd/name 4.0)HMDB
alpha -MethylfuranHMDB
MethylfuranHMDB
Methylfuran (dot)HMDB
Chemical FormulaC5H6O
Average Molecular Weight82.1005
Monoisotopic Molecular Weight82.041864814
IUPAC Name2-methylfuran
Traditional Namesilvan
CAS Registry Number534-22-5
SMILES
CC1=CC=CO1
InChI Identifier
InChI=1S/C5H6O/c1-5-3-2-4-6-5/h2-4H,1H3
InChI KeyVQKFNUFAXTZWDK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassHeteroaromatic compounds
Sub ClassNot Available
Direct ParentHeteroaromatic compounds
Alternative Parents
Substituents
  • Heteroaromatic compound
  • Furan
  • Oxacycle
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-87.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3 mg/mL at 20 °CNot Available
LogP1.85Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility12.6 g/LALOGPS
logP1.75ALOGPS
logP1.31ChemAxon
logS-0.81ALOGPS
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area13.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity23.72 m³·mol⁻¹ChemAxon
Polarizability8.85 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]+113.02331661259
DarkChem[M-H]-107.53431661259
DeepCCS[M+H]+122.42730932474
DeepCCS[M-H]-120.53230932474
DeepCCS[M-2H]-155.97230932474
DeepCCS[M+Na]+130.25730932474
AllCCS[M+H]+112.932859911
AllCCS[M+H-H2O]+107.532859911
AllCCS[M+NH4]+117.932859911
AllCCS[M+Na]+119.332859911
AllCCS[M-H]-115.132859911
AllCCS[M+Na-2H]-118.832859911
AllCCS[M+HCOO]-122.832859911

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, 2022.3.02 minutes32390414
Predicted by Siyang on May 30, 202213.0795 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20223.59 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1199.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid539.4 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid218.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid381.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid229.3 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid428.4 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 Acid602.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)490.2 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1051.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid375.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1105.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid398.9 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid417.6 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate616.1 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA474.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water115.2 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-MethylfuranCC1=CC=CO1857.6Standard polar33892256
2-MethylfuranCC1=CC=CO1602.1Standard non polar33892256
2-MethylfuranCC1=CC=CO1611.1Semi standard non polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Breath
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BreathDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Nonalcoholic fatty liver disease		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Perillyl alcohol administration for cancer treatment
  1. Silva CL, Passos M, Camara JS: Solid phase microextraction, mass spectrometry and metabolomic approaches for detection of potential urinary cancer biomarkers--a powerful strategy for breast cancer diagnosis. Talanta. 2012 Jan 30;89:360-8. doi: 10.1016/j.talanta.2011.12.041. Epub 2011 Dec 22. [PubMed:22284503 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012718
KNApSAcK IDC00048276
Chemspider ID10340
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2-Methylfuran
METLIN IDNot Available
PubChem Compound10797
PDB IDNot Available
ChEBI ID88912
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available