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Showing metabocard for gamma-Butyrolactone (HMDB0000549)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:56 UTC
HMDB IDHMDB0000549
Secondary Accession Numbers
  • HMDB00549
Metabolite Identification
Common Namegamma-Butyrolactone
DescriptionGamma-butyrolactone (GBL), also known as 1,4-butanolide or 1,4-lactone, 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. GBL can also be classified as a tetrahydrofuran substituted by an oxo group at position 2. Gamma-butyrolactone is soluble in ethanol and moderately miscible in water. Gamma-butyrolactone is a sweet, caramel, and creamy tasting compound. Gamma-butyrolactone exists in all living species, ranging from bacteria to plants to humans. It can be endogenously produced from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. Outside of the human body, gamma-butyrolactone has been detected, but not quantified in, several different foods, such as pepper (c. annuum), yellow bell peppers, orange bell peppers, soy beans, evergreen blackberries and a variety of wines (at a concentration of 5 ug/mL) (PMID: 15939164 ). This could make gamma-butyrolactone a potential biomarker for the consumption of these foods. Gamma-butyrolactone is rapidly converted into gamma-hydroxybutyrate by paraoxonase (lactonase) enzymes, found in the blood. Because it can serve as a prodrug for gamma-hydroxybutyrate (GHB), Gamma-butyrolactone is commonly used as a recreational CNS depressant with effects similar to those of barbiturates. Industrially gamma-butyrolactone is used as a common solvent for polymers and alcohols, a chemical intermediate, a raw material for pharmaceuticals, and as a paint stripper, superglue remover, and a stain remover.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000549 (gamma-Butyrolactone)

  Mrv1652305271900132D          

  6  6  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 O   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
    1.2352    0.6294    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
    0.1553   -0.1553    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
M  END
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3D MOL for HMDB0000549 (gamma-Butyrolactone)

HMDB0000549
     RDKit          3D
gamma-Butyrolactone
 12 12  0  0  0  0  0  0  0  0999 V2000
    2.4088    1.0720   -0.0734 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2306    0.6565    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7532   -0.7691    0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6742   -0.5502   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0033    0.7113    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1274    1.5006    0.0676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6617   -1.0392    1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367   -1.4233   -0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6162   -0.3192   -1.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3305   -1.3853   -0.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9415    0.3921    1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9525    1.1538    0.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  3  7  1  0
  3  8  1  0
  4  9  1  0
  4 10  1  0
  5 11  1  0
  5 12  1  0
M  END
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3D SDF for HMDB0000549 (gamma-Butyrolactone)

  Mrv1652305271900132D          

  6  6  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 O   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
    1.2352    0.6294    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
    0.1553   -0.1553    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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000549

> <DATABASE_NAME>
hmdb

> <SMILES>
O=C1CCCO1

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2

> <INCHI_KEY>
YEJRWHAVMIAJKC-UHFFFAOYSA-N

> <FORMULA>
C4H6O2

> <MOLECULAR_WEIGHT>
86.0892

> <EXACT_MASS>
86.036779436

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
8.23114899325824

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
oxolan-2-one

> <ALOGPS_LOGP>
-0.11

> <JCHEM_LOGP>
0.14955130566666652

> <ALOGPS_LOGS>
0.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.033665932739647

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
20.3081

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.38e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butyrolactone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0000549 (gamma-Butyrolactone)

HMDB0000549
     RDKit          3D
gamma-Butyrolactone
 12 12  0  0  0  0  0  0  0  0999 V2000
    2.4088    1.0720   -0.0734 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2306    0.6565    0.0006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7532   -0.7691    0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6742   -0.5502   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0033    0.7113    0.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1274    1.5006    0.0676 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6617   -1.0392    1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3367   -1.4233   -0.5972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6162   -0.3192   -1.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3305   -1.3853   -0.2254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9415    0.3921    1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9525    1.1538    0.0429 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  3  7  1  0
  3  8  1  0
  4  9  1  0
  4 10  1  0
  5 11  1  0
  5 12  1  0
M  END
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PDB for HMDB0000549 (gamma-Butyrolactone)

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  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   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  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    2                                                       
MASTER        0    0    0    0    0    0    0    0    6    0   12    0
END
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3D PDB for HMDB0000549 (gamma-Butyrolactone)

COMPND    HMDB0000549
HETATM    1  O1  UNL     1       2.409   1.072  -0.073  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.231   0.656   0.001  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.753  -0.769   0.033  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.674  -0.550  -0.487  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.003   0.711   0.325  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.127   1.501   0.068  1.00  0.00           O  
HETATM    7  H1  UNL     1       0.662  -1.039   1.084  1.00  0.00           H  
HETATM    8  H2  UNL     1       1.337  -1.423  -0.597  1.00  0.00           H  
HETATM    9  H3  UNL     1      -0.616  -0.319  -1.560  1.00  0.00           H  
HETATM   10  H4  UNL     1      -1.331  -1.385  -0.225  1.00  0.00           H  
HETATM   11  H5  UNL     1      -0.941   0.392   1.390  1.00  0.00           H  
HETATM   12  H6  UNL     1      -1.952   1.154   0.043  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    6
CONECT    3    4    7    8
CONECT    4    5    9   10
CONECT    5    6   11   12
END
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SMILES for HMDB0000549 (gamma-Butyrolactone)

O=C1CCCO1
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INCHI for HMDB0000549 (gamma-Butyrolactone)

InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC4H6O2
Average Molecular Weight86.0892
Monoisotopic Molecular Weight86.036779436
IUPAC Nameoxolan-2-one
Traditional Namebutyrolactone
CAS Registry Number96-48-0
SMILES
O=C1CCCO1
InChI Identifier
InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2
InChI KeyYEJRWHAVMIAJKC-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
Health effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationIndirect biological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-45 °CNot Available
Boiling Point204.00 to 205.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1000 mg/mLNot Available
LogP-0.64HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • Adipose Tissue
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.28 +/- 0.16 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04699
Phenol Explorer Compound IDNot Available
FooDB IDFDB003392
KNApSAcK IDC00053167
Chemspider ID7029
KEGG Compound IDC01770
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGamma-Butyrolactone
METLIN ID5533
PubChem Compound7302
PDB IDNot Available
ChEBI ID42639
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1028441
References
Synthesis ReferenceZhu, Yulei; Li, Yongwang; Xiang, Hongwei; Su, Hualian; Wu, Jiaxiang. Process for preparation of g-butyrolactone with high yield and selectivity. Faming Zhuanli Shenqing Gongkai Shuomingshu (2001), 13 pp.
Material Safety Data Sheet (MSDS)Not Available
General References