Showing metabocard for gamma-butyrolactone (MMDBc0033453)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:49:15 UTC
Update Date2022-08-31 22:36:12 UTC
Metabolite IDMMDBc0033453
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
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f1240b5f258>


  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 #<Metabolite:0x00007f1240b5f258>

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 #<Metabolite:0x00007f1240b5f258>


  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>
MMDBc0033453

> <DATABASE_NAME>
MIME

> <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 #<Metabolite:0x00007f1240b5f258>

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 #<Metabolite:0x00007f1240b5f258>

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 #<Metabolite:0x00007f1240b5f258>

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 #<Metabolite:0x00007f1240b5f258>

O=C1CCCO1
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INCHI for #<Metabolite:0x00007f1240b5f258>

InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2
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Synonyms
ValueSource
1,2-ButanolideChEBI
1,4-ButanolideChEBI
1,4-LactoneChEBI
4-ButyrolactoneChEBI
4-Deoxytetronic acidChEBI
4-Hydroxybutyric acid lactoneChEBI
ButyrolactoneChEBI
Dihydro-2(3H)-furanoneChEBI
gamma-ButanolactoneChEBI
gamma-Hydroxybutyric acid lactoneChEBI
gamma-HydroxybutyrolactoneChEBI
Tetrahydrofuran-2-oneChEBI
4-DeoxytetronateGenerator
4-Hydroxybutyrate lactoneGenerator
g-ButanolactoneGenerator
Γ-butanolactoneGenerator
g-Hydroxybutyrate lactoneGenerator
g-Hydroxybutyric acid lactoneGenerator
gamma-Hydroxybutyrate lactoneGenerator
Γ-hydroxybutyrate lactoneGenerator
Γ-hydroxybutyric acid lactoneGenerator
g-HydroxybutyrolactoneGenerator
Γ-hydroxybutyrolactoneGenerator
g-ButyrolactoneGenerator
Γ-butyrolactoneGenerator
1-Oxacyclopentan-2-oneHMDB
2,3,4,5-Tetrahydro-2-furanoneHMDB
2-OxolanoneHMDB
2-OxotetrahydrofuranHMDB
4,5-Dihydro-2(3H)-furanoneHMDB
4-ButanolideHMDB
4-Hydroxy-butanoateHMDB
4-Hydroxy-butanoic acidHMDB
4-Hydroxy-butanoic acid g-lactoneHMDB
4-HydroxybutanoateHMDB
4-Hydroxybutanoic acidHMDB
4-Hydroxybutanoic acid lactoneHMDB
Butyric acid lactoneHMDB
g-ButalactoneHMDB
g-ButyryllactoneHMDB
gamma-ButalactoneHMDB
gamma-ButyryllactoneHMDB
GBLHMDB
Paint clean gHMDB
Tetrahydro-2-furanoneHMDB
4 ButyrolactoneHMDB
gamma ButyrolactoneHMDB
Furanone, tetrahydro 2HMDB
1,4 ButanolideHMDB
4 Hydroxybutyric acid lactoneHMDB
Lactone, 4-hydroxybutyric acidHMDB
gamma-ButyrolactoneMeSH
Molecular FormulaC4H6O2
Average Mass86.0892
Monoisotopic Mass86.036779436
IUPAC Nameoxolan-2-one
Traditional Namebutyrolactone
CAS Registry Number187997-16-6
SMILES
O=C1CCCO1
InChI Identifier
InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2
InChI KeyYEJRWHAVMIAJKC-UHFFFAOYSA-N