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Showing NP-Card for Gamma-Butyrolactone (NP0000076)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:39:42 UTC
NP-MRD IDNP0000076
Secondary Accession NumbersNone
Natural Product 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 NP0000076 (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 NP0000076 (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 NP0000076 (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>
NP0000076

> <DATABASE_NAME>
NP-MRD

> <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

$$$$
Download

3D-SDF for NP0000076 (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
Download

PDB for NP0000076 (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 NP0000076 (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 NP0000076 (Gamma-Butyrolactone)

O=C1CCCO1
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INCHI for NP0000076 (Gamma-Butyrolactone)

InChI=1S/C4H6O2/c5-4-2-1-3-6-4/h1-3H2
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View in JSmol
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
Chemical FormulaC4H6O2
Average Mass86.0892 Da
Monoisotopic Mass86.03678 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-09View Spectrum
Species
Species of Origin
Species NameSourceReference
Aesculus hippocastanumLOTUS Database
Aethus indicusLOTUS Database
Ananas comosusFooDB
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
CervidaeFooDB
Cervus canadensisFooDB
Citrullus lanatusLOTUS Database
Coffea arabicaKNApSAcK Database
Coffea canephoraKNApSAcK Database
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Glycine maxFooDB
Glycyrrhiza glabraLOTUS Database
Gossypium hirsutumLOTUS Database
Lagopus mutaFooDB
Lavandula angustifoliaLOTUS Database
LeporidaeFooDB
Lepus timidusFooDB
Mandragora autumnalisKNApSAcK Database
Mangifera indicaLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Prunus aviumKNApSAcK Database
Streptomyces albidoflavusLOTUS Database
Streptomyces coelicolorLOTUS Database
Streptomyces nodosusLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Vaccinium myrtillusFooDB
Vigna radiataFooDB
Vitis viniferaLOTUS Database
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
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point-45 °Chttps://en.wikipedia.org/wiki/Gamma-Butyrolactone
Boiling Point204 °Chttps://en.wikipedia.org/wiki/Gamma-Butyrolactone
Water Solubility1000 mg/mLNot Available
LogP-0.64Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility238 g/LALOGPS
logP-0.11ALOGPS
logP0.15ChemAxon
logS0.44ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity20.31 m³·mol⁻¹ChemAxon
Polarizability8.23 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000549
DrugBank IDDB04699
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDrw1028441
References
General References
  1. Fukui Y, Matsusima E, Muramoto K, Nagai N, Ohama K, Yamashita K: Validation of a simple gas chromatographic-mass spectrometric method for the determination of gamma-butyrolactone in human plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Feb 25;785(1):73-80. [PubMed:12535840 ]
  2. Thupari JN, Landree LE, Ronnett GV, Kuhajda FP: C75 increases peripheral energy utilization and fatty acid oxidation in diet-induced obesity. Proc Natl Acad Sci U S A. 2002 Jul 9;99(14):9498-502. Epub 2002 Jun 11. [PubMed:12060712 ]
  3. Wood M, Laloup M, Samyn N, Morris MR, de Bruijn EA, Maes RA, Young MS, Maes V, De Boeck G: Simultaneous analysis of gamma-hydroxybutyric acid and its precursors in urine using liquid chromatography-tandem mass spectrometry. J Chromatogr A. 2004 Nov 12;1056(1-2):83-90. [PubMed:15595536 ]
  4. Quintanilla RA, Orellana DI, Gonzalez-Billault C, Maccioni RB: Interleukin-6 induces Alzheimer-type phosphorylation of tau protein by deregulating the cdk5/p35 pathway. Exp Cell Res. 2004 Apr 15;295(1):245-57. [PubMed:15051507 ]
  5. Knust U, Hull WE, Spiegelhalder B, Bartsch H, Strowitzki T, Owen RW: Analysis of enterolignan glucuronides in serum and urine by HPLC-ESI-MS. Food Chem Toxicol. 2006 Jul;44(7):1038-49. Epub 2006 Feb 20. [PubMed:16488523 ]
  6. Oshima I, Saito S, Shiota K, Miyake A, Oka Y, Nakayama R: Kinetic study on disappearance of gamma-butyrolactone-gamma-carbonyl-L-histidyl-L-prolinamide (DN-1417) from plasma using a radioimmunoassay for DN-1417 isobutylamide. J Pharmacobiodyn. 1983 Mar;6(3):202-8. [PubMed:6410041 ]
  7. Yeatman DT, Reid K: A study of urinary endogenous gamma-hydroxybutyrate (GHB) levels. J Anal Toxicol. 2003 Jan-Feb;27(1):40-2. [PubMed:12587682 ]
  8. Elliott S, Burgess V: The presence of gamma-hydroxybutyric acid (GHB) and gamma-butyrolactone (GBL) in alcoholic and non-alcoholic beverages. Forensic Sci Int. 2005 Jul 16;151(2-3):289-92. doi: 10.1016/j.forsciint.2005.02.014. [PubMed:15939164 ]