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Showing metabocard for 3-Methylbutyrolactone (HMDB0002167)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:39 UTC
Update Date2023-02-21 17:16:13 UTC
HMDB IDHMDB0002167
Secondary Accession Numbers
  • HMDB02167
Metabolite Identification
Common Name3-Methylbutyrolactone
Description3-Methylbutyrolactone 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. 3-Methylbutyrolactone has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and pulses. This could make 3-methylbutyrolactone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3-Methylbutyrolactone.
Structure
Data?1676999773
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0002167 (3-Methylbutyrolactone)

  Mrv0541 02231219242D          

  7  7  0  0  0  0            999 V2000
   24.7459  -13.9043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1981  -13.6744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8484  -11.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3334  -12.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0784  -13.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1584  -12.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4133  -13.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  0  0  0  0
  2  7  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
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3D MOL for HMDB0002167 (3-Methylbutyrolactone)

HMDB0002167
     RDKit          3D
3-Methylbutyrolactone
 15 15  0  0  0  0  0  0  0  0999 V2000
   -1.2324   -0.5401    0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5385    0.0075   -0.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0369    1.4013   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802    1.2607    0.2494 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486   -0.1026    0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2355   -0.6627    1.3151 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7832   -0.7643   -0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713   -1.2980    0.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6732    0.2755    1.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5089   -1.0755    1.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1479   -0.0887   -1.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6392    1.8758    0.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0588    2.0235   -1.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -0.4811   -1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559   -1.8312   -0.5046 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
  7 14  1  0
  7 15  1  0
M  END
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3D SDF for HMDB0002167 (3-Methylbutyrolactone)

  Mrv0541 02231219242D          

  7  7  0  0  0  0            999 V2000
   24.7459  -13.9043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1981  -13.6744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8484  -11.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3334  -12.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0784  -13.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1584  -12.6347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4133  -13.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  5  1  0  0  0  0
  1  7  1  0  0  0  0
  2  7  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002167

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1COC(=O)C1

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

> <INCHI_KEY>
ALZLTHLQMAFAPA-UHFFFAOYSA-N

> <FORMULA>
C5H8O2

> <MOLECULAR_WEIGHT>
100.1158

> <EXACT_MASS>
100.0524295

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
10.124309203738143

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methyloxolan-2-one

> <ALOGPS_LOGP>
0.41

> <JCHEM_LOGP>
0.5145241320000001

> <ALOGPS_LOGS>
-0.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.037214939155667

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
24.7797

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.04e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methyldihydro-2(3H)-furanone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0002167 (3-Methylbutyrolactone)

HMDB0002167
     RDKit          3D
3-Methylbutyrolactone
 15 15  0  0  0  0  0  0  0  0999 V2000
   -1.2324   -0.5401    0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5385    0.0075   -0.5524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0369    1.4013   -0.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802    1.2607    0.2494 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486   -0.1026    0.4508 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2355   -0.6627    1.3151 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7832   -0.7643   -0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9713   -1.2980    0.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6732    0.2755    1.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5089   -1.0755    1.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1479   -0.0887   -1.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6392    1.8758    0.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0588    2.0235   -1.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -0.4811   -1.5928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559   -1.8312   -0.5046 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
  7 14  1  0
  7 15  1  0
M  END
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PDB for HMDB0002167 (3-Methylbutyrolactone)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      46.192 -25.955   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      48.903 -25.526   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      44.517 -22.339   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      45.422 -23.585   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      44.946 -25.050   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      46.962 -23.585   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      47.438 -25.050   0.000  0.00  0.00           C+0
CONECT    1    5    7                                                       
CONECT    2    7                                                            
CONECT    3    4                                                            
CONECT    4    3    5    6                                                  
CONECT    5    1    4                                                       
CONECT    6    4    7                                                       
CONECT    7    1    2    6                                                  
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END
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3D PDB for HMDB0002167 (3-Methylbutyrolactone)

COMPND    HMDB0002167
HETATM    1  C1  UNL     1      -1.232  -0.540   0.680  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.539   0.007  -0.552  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.037   1.401  -0.291  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.280   1.261   0.249  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.549  -0.103   0.451  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.236  -0.663   1.315  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.783  -0.764  -0.665  1.00  0.00           C  
HETATM    8  H1  UNL     1      -1.971  -1.298   0.378  1.00  0.00           H  
HETATM    9  H2  UNL     1      -1.673   0.276   1.304  1.00  0.00           H  
HETATM   10  H3  UNL     1      -0.509  -1.076   1.357  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.148  -0.089  -1.458  1.00  0.00           H  
HETATM   12  H5  UNL     1      -0.639   1.876   0.517  1.00  0.00           H  
HETATM   13  H6  UNL     1      -0.059   2.024  -1.188  1.00  0.00           H  
HETATM   14  H7  UNL     1       1.304  -0.481  -1.593  1.00  0.00           H  
HETATM   15  H8  UNL     1       0.656  -1.831  -0.505  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    7   11
CONECT    3    4   12   13
CONECT    4    5
CONECT    5    6    6    7
CONECT    7   14   15
END
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SMILES for HMDB0002167 (3-Methylbutyrolactone)

CC1COC(=O)C1
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INCHI for HMDB0002167 (3-Methylbutyrolactone)

InChI=1S/C5H8O2/c1-4-2-5(6)7-3-4/h4H,2-3H2,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(S)-(-)-3-Methyl-gamma-butyrolactoneHMDB
(S)-Dihydro-4-methylfuran-2(3H)-oneHMDB
4-Methyldihydro-2(3H)-furanoneHMDB
Dihydro-4-methyl-2(3H)-furanoneHMDB
S-beta-Methyl-gamma-butyrolactoneHMDB
3-MethylbutyrolactoneMeSH
Chemical FormulaC5H8O2
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
IUPAC Name4-methyloxolan-2-one
Traditional Name4-methyldihydro-2(3H)-furanone
CAS Registry Number1679-49-8
SMILES
CC1COC(=O)C1
InChI Identifier
InChI=1S/C5H8O2/c1-4-2-5(6)7-3-4/h4H,2-3H2,1H3
InChI KeyALZLTHLQMAFAPA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point206.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility93810 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.270 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
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 IDFDB016729
KNApSAcK IDNot Available
Chemspider ID88906
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6521
PubChem Compound98451
PDB IDNot Available
ChEBI ID173338
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1416011
References
Synthesis ReferenceBeavers, William Anthony; Ignatchenko, Alexey Victorovitch. Process for preparing a- and b-methyl-g-butyrolactone and 3-methyltetrahydrofuran. Eur. Pat. Appl. (2004), 26 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Truscott RJ, Malegan D, McCairns E, Burke D, Hick L, Sims P, Halpern B, Tanaka K, Sweetman L, Nyhan WL, Hammond J, Bumack C, Haan EA, Danks DM: New metabolites in isovaleric acidemia. Clin Chim Acta. 1981 Mar 5;110(2-3):187-203. [PubMed:6452974 ]
  2. Divry P, Vianey-Liaud C, Cotte J: Routine gas chromatographic/mass spectrometric analysis of urinary organic acids. Results over a three-year period. Biomed Environ Mass Spectrom. 1987 Nov;14(11):663-8. [PubMed:2962675 ]
  3. Burke DG, Halpern B, Malegan D, McCairns E, Danks D, Schlesinger P, Wilken B: Profiles of urinary volatiles from metabolic disorders characterized by unusual odors. Clin Chem. 1983 Oct;29(10):1834-8. [PubMed:6616835 ]