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Showing metabocard for 2,5-Dimethylfuran (HMDB0033182)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:54:14 UTC
Update Date2023-02-21 17:23:12 UTC
HMDB IDHMDB0033182
Secondary Accession Numbers
  • HMDB33182
Metabolite Identification
Common Name2,5-Dimethylfuran
Description2,5-Dimethylfuran is a derivative of furan. It is a heterocyclic compound of the formula C6H8O. While it may be abbreviated DMF, it should not be confused with dimethylformamide. 2,5-Dimethylfuran is a maillard product. 2,5-Dimethylfuran has been identified as one of the components of cigar smoke with low cilatoxicity (ability to adversely affect the cilia in the respiratory tract that are responsible for removing foreign particles). Its blood concentration can be used as a biomarker for smoking. 2,5-Dimethylfuran, together with 2,5-hexanedione and 4,5-dihydroxy-2-hexanone, is one of the main metabolites of hexane in humans, which play a role in the mechanism for the neurotoxicity of hexane.Recent advances have increased its attractiveness as a biofuel.
Structure
Data?1677000192
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0033182 (2,5-Dimethylfuran)


  Mrv1652305261923562D          

  7  7  0  0  0  0            999 V2000
   -0.3297   -0.8227    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
    0.9803   -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    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
M  END
Download

3D MOL for HMDB0033182 (2,5-Dimethylfuran)

HMDB0033182
     RDKit          3D
2,5-Dimethylfuran
 15 15  0  0  0  0  0  0  0  0999 V2000
    2.5264   -0.5257   -0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0943   -0.0695   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590    1.1965    0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7189    1.1690    0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0837   -0.1135   -0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4978   -0.6223   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0163   -0.7852   -0.2108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5688   -1.1272   -1.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7747   -1.2073    0.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1908    0.3382   -0.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3091    2.0463    0.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3758    2.0127    0.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1207   -0.0991    0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5178   -1.7095    0.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8247   -0.5034   -1.1969 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
  5  7  1  0
  7  2  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  6 13  1  0
  6 14  1  0
  6 15  1  0
M  END
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3D SDF for HMDB0033182 (2,5-Dimethylfuran)


  Mrv1652305261923562D          

  7  7  0  0  0  0            999 V2000
   -0.3297   -0.8227    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
    0.9803   -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    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033182

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=C(C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3

> <INCHI_KEY>
GSNUFIFRDBKVIE-UHFFFAOYSA-N

> <FORMULA>
C6H8O

> <MOLECULAR_WEIGHT>
96.1271

> <EXACT_MASS>
96.057514878

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.08581108665272

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,5-dimethylfuran

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
1.5126139823333333

> <ALOGPS_LOGS>
-1.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.737097440646146

> <JCHEM_POLAR_SURFACE_AREA>
13.14

> <JCHEM_REFRACTIVITY>
28.870800000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.55e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dimethylfuran

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0033182 (2,5-Dimethylfuran)

HMDB0033182
     RDKit          3D
2,5-Dimethylfuran
 15 15  0  0  0  0  0  0  0  0999 V2000
    2.5264   -0.5257   -0.1616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0943   -0.0695   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590    1.1965    0.2970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7189    1.1690    0.2997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0837   -0.1135   -0.0293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4978   -0.6223   -0.1508 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0163   -0.7852   -0.2108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5688   -1.1272   -1.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7747   -1.2073    0.7009 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1908    0.3382   -0.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3091    2.0463    0.5121 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3758    2.0127    0.5225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1207   -0.0991    0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5178   -1.7095    0.0949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8247   -0.5034   -1.1969 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
  5  7  1  0
  7  2  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  3 11  1  0
  4 12  1  0
  6 13  1  0
  6 14  1  0
  6 15  1  0
M  END
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PDB for HMDB0033182 (2,5-Dimethylfuran)

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      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.290  -0.290   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      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    1    3    7                                                  
CONECT    6    2    4    7                                                  
CONECT    7    5    6                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END
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3D PDB for HMDB0033182 (2,5-Dimethylfuran)

COMPND    HMDB0033182
HETATM    1  C1  UNL     1       2.526  -0.526  -0.162  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.094  -0.070  -0.033  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.659   1.197   0.297  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.719   1.169   0.300  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.084  -0.113  -0.029  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.498  -0.622  -0.151  1.00  0.00           C  
HETATM    7  O1  UNL     1       0.016  -0.785  -0.211  1.00  0.00           O  
HETATM    8  H1  UNL     1       2.569  -1.127  -1.088  1.00  0.00           H  
HETATM    9  H2  UNL     1       2.775  -1.207   0.701  1.00  0.00           H  
HETATM   10  H3  UNL     1       3.191   0.338  -0.142  1.00  0.00           H  
HETATM   11  H4  UNL     1       1.309   2.046   0.512  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.376   2.013   0.522  1.00  0.00           H  
HETATM   13  H6  UNL     1      -3.121  -0.099   0.586  1.00  0.00           H  
HETATM   14  H7  UNL     1      -2.518  -1.709   0.095  1.00  0.00           H  
HETATM   15  H8  UNL     1      -2.825  -0.503  -1.197  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    3    7
CONECT    3    4   11
CONECT    4    5    5   12
CONECT    5    6    7
CONECT    6   13   14   15
END
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SMILES for HMDB0033182 (2,5-Dimethylfuran)

CC1=CC=C(C)O1
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INCHI for HMDB0033182 (2,5-Dimethylfuran)

InChI=1S/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2,5-Dimethyl-furanChEBI
2,5-DimethylfuraneChEBI
Chemical FormulaC6H8O
Average Molecular Weight96.1271
Monoisotopic Molecular Weight96.057514878
IUPAC Name2,5-dimethylfuran
Traditional Name2,5-dimethylfuran
CAS Registry Number625-86-5
SMILES
CC1=CC=C(C)O1
InChI Identifier
InChI=1S/C6H8O/c1-5-3-4-6(2)7-5/h3-4H,1-2H3
InChI KeyGSNUFIFRDBKVIE-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 locationSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-63 °CNot Available
Boiling Point92.00 to 94.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1466 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.24Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.55 g/LALOGPS
logP2.17ALOGPS
logP1.51ChemAxon
logS-1.1ALOGPS
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area13.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity28.87 m³·mol⁻¹ChemAxon
Polarizability11.09 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]+117.72131661259
DarkChem[M-H]-113.97931661259
DeepCCS[M+H]+127.9230932474
DeepCCS[M-H]-125.91130932474
DeepCCS[M-2H]-161.52830932474
DeepCCS[M+Na]+136.18330932474
AllCCS[M+H]+115.332859911
AllCCS[M+H-H2O]+110.132859911
AllCCS[M+NH4]+120.232859911
AllCCS[M+Na]+121.632859911
AllCCS[M-H]-117.132859911
AllCCS[M+Na-2H]-120.132859911
AllCCS[M+HCOO]-123.532859911

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. 3.88 minutes32390414
Predicted by Siyang on May 30, 202214.8041 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.7 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1349.0 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid582.2 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 Acid406.2 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid252.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid461.0 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 Acid651.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)426.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1203.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid432.5 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1279.4 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid443.8 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid431.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate587.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA475.8 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water73.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,5-DimethylfuranCC1=CC=C(C)O1927.5Standard polar33892256
2,5-DimethylfuranCC1=CC=C(C)O1714.2Standard non polar33892256
2,5-DimethylfuranCC1=CC=C(C)O1700.1Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000166 uMAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Ulcerative colitis		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Crohn's disease 		details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)FemaleBreast cancer details
Associated Disorders and Diseases
Disease References
Ulcerative colitis
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
Crohn's disease
  1. De Preter V, Machiels K, Joossens M, Arijs I, Matthys C, Vermeire S, Rutgeerts P, Verbeke K: Faecal metabolite profiling identifies medium-chain fatty acids as discriminating compounds in IBD. Gut. 2015 Mar;64(3):447-58. doi: 10.1136/gutjnl-2013-306423. Epub 2014 May 8. [PubMed:24811995 ]
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 IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB011193
KNApSAcK IDNot Available
Chemspider ID11763
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2,5-Dimethylfuran
METLIN IDNot Available
PubChem Compound12266
PDB IDNot Available
ChEBI ID89052
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029794
Good Scents IDrw1040081
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.. .