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Showing metabocard for Dihydro-5-methyl-2(3H)-furanone (HMDB0033840)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 18:36:49 UTC
Update Date2023-02-21 17:23:40 UTC
HMDB IDHMDB0033840
Secondary Accession Numbers
  • HMDB33840
Metabolite Identification
Common NameDihydro-5-methyl-2(3H)-furanone
DescriptionDihydro-5-methyl-2(3H)-furanone, also known as 4-hydroxypentanoic acid lactone or 4-methyl-gamma-butyrolactone, belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Thus, dihydro-5-methyl-2(3H)-furanone is considered to be a fatty ester lipid molecule. Dihydro-5-methyl-2(3H)-furanone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Data?1677000220
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0033840 (Dihydro-5-methyl-2(3H)-furanone)

  Mrv1652305271900092D          

  7  7  0  0  0  0            999 V2000
   -1.4021    0.7833    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
   -0.7421   -0.5358    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
    0.5771   -0.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021   -0.1233    0.0000 O   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  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
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3D MOL for HMDB0033840 (Dihydro-5-methyl-2(3H)-furanone)

HMDB0033840
     RDKit          3D
Dihydro-5-methyl-2(3H)-furanone
 15 15  0  0  0  0  0  0  0  0999 V2000
   -1.8849    0.3024   -0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6298    0.4079    0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1213   -0.8714    0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5616   -0.5502    0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4907    0.7967   -0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434    1.3834   -1.0273 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2306    1.3222   -0.3113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5922   -0.4650   -0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636    1.3228   -0.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5801    0.1456   -1.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247    0.8631    1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0730   -1.2339    1.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2355   -1.6865   -0.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0047   -1.2933   -0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1854   -0.4438    1.0814 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  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
  3 13  1  0
  4 14  1  0
  4 15  1  0
M  END
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3D SDF for HMDB0033840 (Dihydro-5-methyl-2(3H)-furanone)

  Mrv1652305271900092D          

  7  7  0  0  0  0            999 V2000
   -1.4021    0.7833    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
   -0.7421   -0.5358    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
    0.5771   -0.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021   -0.1233    0.0000 O   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  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033840

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O2/c1-4-2-3-5(6)7-4/h4H,2-3H2,1H3

> <INCHI_KEY>
GAEKPEKOJKCEMS-UHFFFAOYSA-N

> <FORMULA>
C5H8O2

> <MOLECULAR_WEIGHT>
100.1158

> <EXACT_MASS>
100.0524295

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.161339832875981

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methyloxolan-2-one

> <ALOGPS_LOGP>
0.36

> <JCHEM_LOGP>
0.5661263303333333

> <ALOGPS_LOGS>
-0.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.041941973796066

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
24.7269

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.26e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma-valerolactone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0033840 (Dihydro-5-methyl-2(3H)-furanone)

HMDB0033840
     RDKit          3D
Dihydro-5-methyl-2(3H)-furanone
 15 15  0  0  0  0  0  0  0  0999 V2000
   -1.8849    0.3024   -0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6298    0.4079    0.3581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1213   -0.8714    0.4809 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5616   -0.5502    0.1501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4907    0.7967   -0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434    1.3834   -1.0273 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2306    1.3222   -0.3113 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5922   -0.4650   -0.0947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3636    1.3228   -0.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5801    0.1456   -1.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247    0.8631    1.3713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0730   -1.2339    1.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2355   -1.6865   -0.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0047   -1.2933   -0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1854   -0.4438    1.0814 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  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
  3 13  1  0
  4 14  1  0
  4 15  1  0
M  END
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PDB for HMDB0033840 (Dihydro-5-methyl-2(3H)-furanone)

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  C   UNK     0      -2.617   1.462   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.385   0.538   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.385  -1.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.153  -1.462   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.077  -0.230   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.617  -0.230   0.000  0.00  0.00           O+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 HMDB0033840 (Dihydro-5-methyl-2(3H)-furanone)

COMPND    HMDB0033840
HETATM    1  C1  UNL     1      -1.885   0.302  -0.462  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.630   0.408   0.358  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.121  -0.871   0.481  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.562  -0.550   0.150  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.491   0.797  -0.457  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.443   1.383  -1.027  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.231   1.322  -0.311  1.00  0.00           O  
HETATM    8  H1  UNL     1      -2.592  -0.465  -0.095  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.364   1.323  -0.436  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.580   0.146  -1.520  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.825   0.863   1.371  1.00  0.00           H  
HETATM   12  H5  UNL     1       0.073  -1.234   1.540  1.00  0.00           H  
HETATM   13  H6  UNL     1      -0.235  -1.687  -0.166  1.00  0.00           H  
HETATM   14  H7  UNL     1       2.005  -1.293  -0.509  1.00  0.00           H  
HETATM   15  H8  UNL     1       2.185  -0.444   1.081  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    7   11
CONECT    3    4   12   13
CONECT    4    5   14   15
CONECT    5    6    6    7
END
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SMILES for HMDB0033840 (Dihydro-5-methyl-2(3H)-furanone)

CC1CCC(=O)O1
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INCHI for HMDB0033840 (Dihydro-5-methyl-2(3H)-furanone)

InChI=1S/C5H8O2/c1-4-2-3-5(6)7-4/h4H,2-3H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Name5-methyloxolan-2-one
Traditional Namegamma-valerolactone
CAS Registry Number57129-69-8
SMILES
CC1CCC(=O)O1
InChI Identifier
InChI=1S/C5H8O2/c1-4-2-3-5(6)7-4/h4H,2-3H2,1H3
InChI KeyGAEKPEKOJKCEMS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactones
Sub ClassGamma butyrolactones
Direct ParentGamma butyrolactones
Alternative Parents
Substituents
  • Gamma butyrolactone
  • Tetrahydrofuran
  • 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
RoleNot Available
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-31 °CNot Available
Boiling Point207.00 to 208.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility93810 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.270The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Nonalcoholic fatty liver disease		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 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 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012014
KNApSAcK IDC00055472
Chemspider ID7633
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGamma-Valerolactone
METLIN IDNot Available
PubChem Compound7921
PDB IDNot Available
ChEBI ID48569
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1024031
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.. .