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Showing metabocard for Homofureanol (HMDB0033736)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:29:44 UTC
Update Date2023-02-21 17:23:34 UTC
HMDB IDHMDB0033736
Secondary Accession Numbers
  • HMDB33736
Metabolite Identification
Common NameHomofureanol
DescriptionHomofureanol belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group. Homofureanol is a sweet, butterscotch, and candy tasting compound. Homofureanol has been detected, but not quantified in, several different foods, such as sorghums (Sorghum bicolor), sweet oranges (Citrus sinensis), silver lindens (Tilia argentea), horseradishes (Armoracia rusticana), and green bell peppers (Capsicum annuum). This could make homofureanol a potential biomarker for the consumption of these foods. Homofureanol 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 Homofureanol.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0033736 (Homofureanol)

  Mrv0541 05061307192D          

 10 10  0  0  0  0            999 V2000
   -1.1501   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  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
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  1  0  0  0  0
 10  5  1  0  0  0  0
M  END
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3D MOL for HMDB0033736 (Homofureanol)

HMDB0033736
     RDKit          3D
Homofureanol
 20 20  0  0  0  0  0  0  0  0999 V2000
    2.9178   -0.0038    0.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6984   -0.7711    0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363   -0.0015   -0.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3605   -0.8613   -0.9215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5365   -0.3135   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8714   -0.9640   -0.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3093    0.8544    0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3140    1.6420    0.7167 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1108    1.1325    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126    2.1420    0.4707 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7271   -0.7407    0.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7370    0.5586    1.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3105    0.6601   -0.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9612   -1.7145   -0.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1738   -1.0726    1.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803    0.3228   -1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9821   -1.8153    0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9339   -1.4174   -1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7008   -0.2777   -0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2574    2.6411    0.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9  3  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  6 17  1  0
  6 18  1  0
  6 19  1  0
  8 20  1  0
M  END
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3D SDF for HMDB0033736 (Homofureanol)

  Mrv0541 05061307192D          

 10 10  0  0  0  0            999 V2000
   -1.1501   -0.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.8843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  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
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  1  0  0  0  0
 10  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033736

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1OC(C)=C(O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H10O3/c1-3-5-7(9)6(8)4(2)10-5/h5,8H,3H2,1-2H3

> <INCHI_KEY>
GWCRPYGYVRXVLI-UHFFFAOYSA-N

> <FORMULA>
C7H10O3

> <MOLECULAR_WEIGHT>
142.1525

> <EXACT_MASS>
142.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
14.514653585734772

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-ethyl-4-hydroxy-5-methyl-2,3-dihydrofuran-3-one

> <ALOGPS_LOGP>
0.11

> <JCHEM_LOGP>
0.7312850889999998

> <ALOGPS_LOGS>
0.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.295984186468505

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.536964121228373

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2808376956542675

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
37.81670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0033736 (Homofureanol)

HMDB0033736
     RDKit          3D
Homofureanol
 20 20  0  0  0  0  0  0  0  0999 V2000
    2.9178   -0.0038    0.5963 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6984   -0.7711    0.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7363   -0.0015   -0.6485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3605   -0.8613   -0.9215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5365   -0.3135   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8714   -0.9640   -0.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3093    0.8544    0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3140    1.6420    0.7167 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1108    1.1325    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7126    2.1420    0.4707 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7271   -0.7407    0.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7370    0.5586    1.5436 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3105    0.6601   -0.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9612   -1.7145   -0.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1738   -1.0726    1.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1803    0.3228   -1.5924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9821   -1.8153    0.1600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9339   -1.4174   -1.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7008   -0.2777   -0.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2574    2.6411    0.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9  3  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  0
  2 15  1  0
  3 16  1  0
  6 17  1  0
  6 18  1  0
  6 19  1  0
  8 20  1  0
M  END
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PDB for HMDB0033736 (Homofureanol)

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.147  -1.375   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.770   1.651   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.615  -1.536   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  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.830  -0.290   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    6   10                                                  
CONECT    5    3    7   10                                                  
CONECT    6    4    7    8                                                  
CONECT    7    5    6    9                                                  
CONECT    8    6                                                            
CONECT    9    7                                                            
CONECT   10    4    5                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for HMDB0033736 (Homofureanol)

COMPND    HMDB0033736
HETATM    1  C1  UNL     1       2.918  -0.004   0.596  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.698  -0.771   0.216  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.736  -0.002  -0.648  1.00  0.00           C  
HETATM    4  O1  UNL     1      -0.361  -0.861  -0.922  1.00  0.00           O  
HETATM    5  C4  UNL     1      -1.536  -0.313  -0.438  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.871  -0.964  -0.557  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.309   0.854   0.136  1.00  0.00           C  
HETATM    8  O2  UNL     1      -2.314   1.642   0.717  1.00  0.00           O  
HETATM    9  C7  UNL     1       0.111   1.133   0.045  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.713   2.142   0.471  1.00  0.00           O  
HETATM   11  H1  UNL     1       3.727  -0.741   0.835  1.00  0.00           H  
HETATM   12  H2  UNL     1       2.737   0.559   1.544  1.00  0.00           H  
HETATM   13  H3  UNL     1       3.311   0.660  -0.181  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.961  -1.714  -0.304  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.174  -1.073   1.149  1.00  0.00           H  
HETATM   16  H6  UNL     1       1.180   0.323  -1.592  1.00  0.00           H  
HETATM   17  H7  UNL     1      -2.982  -1.815   0.160  1.00  0.00           H  
HETATM   18  H8  UNL     1      -2.934  -1.417  -1.583  1.00  0.00           H  
HETATM   19  H9  UNL     1      -3.701  -0.278  -0.391  1.00  0.00           H  
HETATM   20  H10 UNL     1      -2.257   2.641   0.748  1.00  0.00           H  
CONECT    1    2   11   12   13
CONECT    2    3   14   15
CONECT    3    4    9   16
CONECT    4    5
CONECT    5    6    7    7
CONECT    6   17   18   19
CONECT    7    8    9
CONECT    8   20
CONECT    9   10   10
END
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SMILES for HMDB0033736 (Homofureanol)

CCC1OC(C)=C(O)C1=O
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INCHI for HMDB0033736 (Homofureanol)

InChI=1S/C7H10O3/c1-3-5-7(9)6(8)4(2)10-5/h5,8H,3H2,1-2H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
4-Hydroxy-2-ethyl-5-methyl-3(2H)-furanoneChEBI
HomofuraneolChEBI
2-Ethyl-4-hydroxy-5-methyl-3(2H)-furanoneHMDB
2-Ethyl-4-hydroxy-5-methyl-3(2H)-furanone (homofuraneol)HMDB
2-Ethyl-4-hydroxy-5-methylfuran-3(2H)-oneHMDB
4-Hydroxy-2- or 5-ethyl-5- and 2-methyl-3(2H)-furanoneHMDB
Ethyl 4-hydroxy-5-methyl-3(2H)-furanone (homofuraneol)HMDB
HEMFHMDB
4-HEMFMeSH, HMDB
4-Hydroxy-5-ethyl-2-methyl-3(2H)-furanoneMeSH, HMDB
5-Ethyl-4-hydroxy-2-methyl-3(2H)-furanoneMeSH, HMDB
EHMF CPDMeSH, HMDB
Chemical FormulaC7H10O3
Average Molecular Weight142.1525
Monoisotopic Molecular Weight142.062994186
IUPAC Name2-ethyl-4-hydroxy-5-methyl-2,3-dihydrofuran-3-one
Traditional Name2-ethyl-4-hydroxy-5-methyl-2H-furan-3-one
CAS Registry Number27538-10-9
SMILES
CCC1OC(C)=C(O)C1=O
InChI Identifier
InChI=1S/C7H10O3/c1-3-5-7(9)6(8)4(2)10-5/h5,8H,3H2,1-2H3
InChI KeyGWCRPYGYVRXVLI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furanones. Furanones are compounds containing a furan ring bearing a ketone group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentFuranones
Alternative Parents
Substituents
  • 3-furanone
  • Vinylogous ester
  • Cyclic ketone
  • Ketone
  • Oxacycle
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point103.00 °C. @ 15.00 mm HgThe Good Scents Company Information System
Water Solubility6178 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.434 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
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 IDFDB011860
KNApSAcK IDNot Available
Chemspider ID31277
KEGG Compound IDNot Available
BioCyc IDCPD-10201
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound33931
PDB IDNot Available
ChEBI ID137995
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1491201
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.. .