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Showing NP-Card for 4-Butyl-gamma-butyrolactone (NP0048239)

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Record Information
Version2.0
Created at2022-03-17 20:53:19 UTC
Updated at2022-03-17 20:53:19 UTC
NP-MRD IDNP0048239
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Butyl-gamma-butyrolactone
Description4-Butyl-gamma-butyrolactone, also known as 5-butyldihydro-2(3H)-furanone or 4-hydroxyoctanoic acid 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. Thus, 4-butyl-gamma-butyrolactone is considered to be a fatty ester lipid molecule. 4-Butyl-gamma-butyrolactone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 4-Butyl-gamma-butyrolactone is a sweet, coconut, and creamy tasting compound. Outside of the human body, 4-Butyl-gamma-butyrolactone is found, on average, in the highest concentration within pineapples and bilberries. 4-Butyl-gamma-butyrolactone has also been detected, but not quantified in, several different foods, such as fruits, asparagus, papaya, peachs, and evergreen blackberries. 4-Butyl-gamma-butyrolactone is found in Akebia trifoliata, Aspalathus linearis, Carica papaya, Fusarium poae, Glycyrrhiza glabra, Mangifera indica and Polygala senega. This could make 4-butyl-gamma-butyrolactone a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048239 (4-Butyl-gamma-butyrolactone)


  Mrv0541 02241218172D          

 10 10  0  0  0  0            999 V2000
   -0.3514    0.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0188   -0.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639   -1.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0611   -1.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3160   -0.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006   -0.0139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8034   -0.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4165   -0.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2011   -0.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8142   -0.8630    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
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3D MOL for NP0048239 (4-Butyl-gamma-butyrolactone)

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3D SDF for NP0048239 (4-Butyl-gamma-butyrolactone)

  Mrv0541 02241218172D          

 10 10  0  0  0  0            999 V2000
   -0.3514    0.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0188   -0.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639   -1.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0611   -1.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3160   -0.2689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1006   -0.0139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8034   -0.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4165   -0.5660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2011   -0.3110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8142   -0.8630    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048239

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC1CCC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C8H14O2/c1-2-3-4-7-5-6-8(9)10-7/h7H,2-6H2,1H3

> <INCHI_KEY>
IPBFYZQJXZJBFQ-UHFFFAOYSA-N

> <FORMULA>
C8H14O2

> <MOLECULAR_WEIGHT>
142.1956

> <EXACT_MASS>
142.099379692

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
16.247355097445087

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-butyloxolan-2-one

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
1.9777860553333335

> <ALOGPS_LOGS>
-1.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0425524221035785

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
38.4529

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-butyloxolan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048239 (4-Butyl-gamma-butyrolactone)
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PDB for NP0048239 (4-Butyl-gamma-butyrolactone)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.656   0.403   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.902  -0.502   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.426  -1.967   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.114  -1.967   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.590  -0.502   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.054  -0.026   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.366  -0.026   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.511  -1.057   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.975  -0.581   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.120  -1.611   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5                                                            
CONECT    7    2    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0048239 (4-Butyl-gamma-butyrolactone)
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SMILES for NP0048239 (4-Butyl-gamma-butyrolactone)
CCCCC1CCC(=O)O1
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INCHI for NP0048239 (4-Butyl-gamma-butyrolactone)
InChI=1S/C8H14O2/c1-2-3-4-7-5-6-8(9)10-7/h7H,2-6H2,1H3
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View in JSmol
Synonyms
ValueSource
4-Butyl-g-butyrolactoneGenerator
4-Butyl-γ-butyrolactoneGenerator
4-Butyl-4-hydroxybutyric acid lactoneHMDB
4-Hydroxyoctanoic acid lactoneHMDB
4-OctanolideHMDB
5-Butyl-tetrahydro-furan-2-oneHMDB
5-Butyldihydro-2(3H)-furanoneHMDB
5-Butyldihydrofuran-2(3H)-oneHMDB
5-Butylhydro-2(3H)-furanoneHMDB
5-Butyltetrahydro-2-furanoneHMDB
8-oxo-5-OctanolideHMDB
FEMA 2796HMDB
gamma-Butyl-gamma-butyrolactoneHMDB
gamma-N-Butyl-gamma-butyrolactoneHMDB
gamma-OctalactoneHMDB
gamma-Octanoic lactoneHMDB
gamma-OctanolactoneHMDB
Octan-4-olideHMDB
Octano-1,4-lactoneHMDB
Octanoic acid, gamma lactoneHMDB
Octanolide-1,4HMDB
g-OctanolideGenerator
Γ-octanolideGenerator
(R)-4-OctanolideMeSH
Chemical FormulaC8H14O2
Average Mass142.1956 Da
Monoisotopic Mass142.09938 Da
IUPAC Name5-butyloxolan-2-one
Traditional Name5-butyloxolan-2-one
CAS Registry Number104-50-7
SMILES
CCCCC1CCC(=O)O1
InChI Identifier
InChI=1S/C8H14O2/c1-2-3-4-7-5-6-8(9)10-7/h7H,2-6H2,1H3
InChI KeyIPBFYZQJXZJBFQ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Akebia trifoliataLOTUS Database
Ananas comosusFooDB
Aspalathus linearisLOTUS Database
Carica papayaLOTUS Database
Carica papaya L.FooDB
Fusarium poaeLOTUS Database
Glycyrrhiza glabraLOTUS Database
Mangifera indicaLOTUS Database
Polygala senegaLOTUS Database
Prunus persicaFooDB
Vaccinium myrtillusFooDB
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
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.94ALOGPS
logP1.98ChemAxon
logS-1.9ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.45 m³·mol⁻¹ChemAxon
Polarizability16.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035422  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014100  
KNApSAcK IDNot Available
Chemspider ID7418  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7704  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available