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Showing metabocard for 5-Methyl-2(3H)-furanone (HMDB0029609)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:26 UTC
Update Date2023-02-21 17:18:52 UTC
HMDB IDHMDB0029609
Secondary Accession Numbers
  • HMDB29609
Metabolite Identification
Common Name5-Methyl-2(3H)-furanone
Description5-Methyl-2(3H)-furanone, also known as beta-angelicalacton or 2-penten-4-olide, belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 5-Methyl-2(3H)-furanone is a sweet, coumarin, and nutty tasting compound. 5-Methyl-2(3H)-furanone has been detected, but not quantified in, blackberries (Rubus) and evergreen blackberries (Rubus laciniatus). This could make 5-methyl-2(3H)-furanone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 5-Methyl-2(3H)-furanone.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0029609 (5-Methyl-2(3H)-furanone)

  Mrv0541 02241218392D          

  7  7  0  0  0  0            999 V2000
    1.4021   -0.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5771   -0.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821   -0.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -0.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    0.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4021    0.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821    0.5358    0.0000 O   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
  2  7  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
  5  7  1  0  0  0  0
M  END
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3D MOL for HMDB0029609 (5-Methyl-2(3H)-furanone)

HMDB0029609
     RDKit          3D
5-Methyl-2(3H)-furanone
 13 13  0  0  0  0  0  0  0  0999 V2000
   -1.6907   -0.2059    0.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4270   -0.3734   -0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371    0.8908   -0.5260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5756    0.7119   -0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6562   -0.6694    0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6911   -1.2036    0.8046 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4543   -1.3171    0.1570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6007    0.5506    1.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4668    0.1865   -0.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0402   -1.1611    0.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7249   -0.7130   -1.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0814    1.8031   -0.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3173    1.5005   -0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  2  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  4 13  1  0
M  END
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3D SDF for HMDB0029609 (5-Methyl-2(3H)-furanone)

  Mrv0541 02241218392D          

  7  7  0  0  0  0            999 V2000
    1.4021   -0.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5771   -0.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821   -0.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -0.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    0.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4021    0.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821    0.5358    0.0000 O   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
  2  7  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
  5  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029609

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1OC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C5H6O2/c1-4-2-3-5(6)7-4/h2-4H,1H3

> <INCHI_KEY>
BGLUXFNVVSVEET-UHFFFAOYSA-N

> <FORMULA>
C5H6O2

> <MOLECULAR_WEIGHT>
98.0999

> <EXACT_MASS>
98.036779436

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
9.440003818526934

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
0.9531906133333332

> <ALOGPS_LOGS>
0.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.603358244772529

> <JCHEM_PKA_STRONGEST_BASIC>
-6.818888195642315

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
25.666200000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α,β-angelica lactone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0029609 (5-Methyl-2(3H)-furanone)

HMDB0029609
     RDKit          3D
5-Methyl-2(3H)-furanone
 13 13  0  0  0  0  0  0  0  0999 V2000
   -1.6907   -0.2059    0.4148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4270   -0.3734   -0.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371    0.8908   -0.5260 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5756    0.7119   -0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6562   -0.6694    0.3330 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6911   -1.2036    0.8046 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4543   -1.3171    0.1570 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6007    0.5506    1.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4668    0.1865   -0.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0402   -1.1611    0.8064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7249   -0.7130   -1.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0814    1.8031   -0.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3173    1.5005   -0.1020 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  2  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  4 13  1  0
M  END
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PDB for HMDB0029609 (5-Methyl-2(3H)-furanone)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       2.617  -0.230   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.077  -0.230   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.153  -1.462   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.385  -1.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.385   0.538   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.617   1.462   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.153   1.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    2    5                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END
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3D PDB for HMDB0029609 (5-Methyl-2(3H)-furanone)

COMPND    HMDB0029609
HETATM    1  C1  UNL     1      -1.691  -0.206   0.415  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.427  -0.373  -0.388  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.337   0.891  -0.526  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.576   0.712  -0.097  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.656  -0.669   0.333  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.691  -1.204   0.805  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.454  -1.317   0.157  1.00  0.00           O  
HETATM    8  H1  UNL     1      -1.601   0.551   1.221  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.467   0.187  -0.290  1.00  0.00           H  
HETATM   10  H3  UNL     1      -2.040  -1.161   0.806  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.725  -0.713  -1.413  1.00  0.00           H  
HETATM   12  H5  UNL     1      -0.081   1.803  -0.921  1.00  0.00           H  
HETATM   13  H6  UNL     1       2.317   1.501  -0.102  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    7   11
CONECT    3    4    4   12
CONECT    4    5   13
CONECT    5    6    6    7
END
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SMILES for HMDB0029609 (5-Methyl-2(3H)-furanone)

CC1OC(=O)C=C1
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INCHI for HMDB0029609 (5-Methyl-2(3H)-furanone)

InChI=1S/C5H6O2/c1-4-2-3-5(6)7-4/h2-4H,1H3
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC5H6O2
Average Molecular Weight98.0999
Monoisotopic Molecular Weight98.036779436
IUPAC Name5-methyl-2,5-dihydrofuran-2-one
Traditional Nameα,β-angelica lactone
CAS Registry Number591-12-8
SMILES
CC1OC(=O)C=C1
InChI Identifier
InChI=1S/C5H6O2/c1-4-2-3-5(6)7-4/h2-4H,1H3
InChI KeyBGLUXFNVVSVEET-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDihydrofurans
Sub ClassFuranones
Direct ParentButenolides
Alternative Parents
Substituents
  • 2-furanone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point18 °CNot Available
Boiling Point208.00 to 210.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility50 mg/mL at 15 °CNot Available
LogP-0.133 (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 IDFDB000776
KNApSAcK IDC00052742
Chemspider ID11070
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11558
PDB IDNot Available
ChEBI ID36436
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1386791
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.. .