Showing NP-Card for 4-Propyl-gamma-butyrolactone (NP0047312)

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Record Information
Version2.0
Created at2022-03-17 20:38:05 UTC
Updated at2022-03-17 20:38:05 UTC
NP-MRD IDNP0047312
Secondary Accession NumbersNone
Natural Product Identification
Common Name4-Propyl-gamma-butyrolactone
DescriptionDihydro-5-propyl-2(3H)-furanone, also known as (+/-)-4-heptanolide or 5-propyl-tetrahydro-furan-2-one, 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, dihydro-5-propyl-2(3H)-furanone is considered to be a fatty ester lipid molecule. Dihydro-5-propyl-2(3H)-furanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Dihydro-5-propyl-2(3H)-furanone is a sweet, caramel, and coconut tasting compound. Outside of the human body, Dihydro-5-propyl-2(3H)-furanone has been detected, but not quantified in, asparagus and peachs. This could make dihydro-5-propyl-2(3H)-furanone a potential biomarker for the consumption of these foods. 4-Propyl-gamma-butyrolactone is found in Bupleurum chinense, Fusarium poae, Glycyrrhiza glabra, Mangifera indica and Polygala senega. Dihydro-5-propyl-2(3H)-furanone is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0047312 (4-Propyl-gamma-butyrolactone)

  Mrv0541 02241209052D          

  9  9  0  0  0  0            999 V2000
   -2.1338    0.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4204    0.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7058    0.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0075    0.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0940   -0.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9008   -0.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3132    0.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7621    0.6253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1338    0.0990    0.0000 O   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
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
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3D MOL for NP0047312 (4-Propyl-gamma-butyrolactone)

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3D SDF for NP0047312 (4-Propyl-gamma-butyrolactone)
  Mrv0541 02241209052D          

  9  9  0  0  0  0            999 V2000
   -2.1338    0.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4204    0.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7058    0.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0075    0.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0940   -0.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9008   -0.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3132    0.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7621    0.6253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1338    0.0990    0.0000 O   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
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047312

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1CCC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C7H12O2/c1-2-3-6-4-5-7(8)9-6/h6H,2-5H2,1H3

> <INCHI_KEY>
VLSVVMPLPMNWBH-UHFFFAOYSA-N

> <FORMULA>
C7H12O2

> <MOLECULAR_WEIGHT>
128.169

> <EXACT_MASS>
128.083729628

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
14.169291261219772

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-propyloxolan-2-one

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.5332173903333333

> <ALOGPS_LOGS>
-1.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.04255210337142

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
33.8519

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-propyloxolan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047312 (4-Propyl-gamma-butyrolactone)
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PDB for NP0047312 (4-Propyl-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  C   UNK     0      -3.983   1.311   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.651   0.542   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.317   1.311   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.014   0.542   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.175  -0.990   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.681  -1.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.451   0.023   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.423   1.167   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       3.983   0.185   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    4    7                                                       
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0047312 (4-Propyl-gamma-butyrolactone)
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SMILES for NP0047312 (4-Propyl-gamma-butyrolactone)
CCCC1CCC(=O)O1
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INCHI for NP0047312 (4-Propyl-gamma-butyrolactone)
InChI=1S/C7H12O2/c1-2-3-6-4-5-7(8)9-6/h6H,2-5H2,1H3
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Synonyms
ValueSource
(+/-)-4-heptanolideHMDB
(+/-)-dihydro-5-propyl-2(3H)-furanoneHMDB
(+/-)-gamma-propyl-gamma-butyrolactoneHMDB
1,4-HeptanolideHMDB
4-Hydroxyheptanoic acid, gamma-lactoneHMDB
4-Propyl-4-hydroxybutanoic acid lactoneHMDB
5-Propyl-tetrahydro-furan-2-oneHMDB
gamma-HeptalactoneHMDB
gamma-HeptanolactoneHMDB
gamma-PropiobutyrolactoneHMDB
gamma-Propyl-gamma-butyrolactoneHMDB
Heptan-4-olideHMDB
Heptanolide-4,1HMDB
4-Propyl-g-butyrolactoneGenerator
4-Propyl-γ-butyrolactoneGenerator
Chemical FormulaC7H12O2
Average Mass128.1690 Da
Monoisotopic Mass128.08373 Da
IUPAC Name5-propyloxolan-2-one
Traditional Name5-propyloxolan-2-one
CAS Registry Number57129-71-2
SMILES
CCCC1CCC(=O)O1
InChI Identifier
InChI=1S/C7H12O2/c1-2-3-6-4-5-7(8)9-6/h6H,2-5H2,1H3
InChI KeyVLSVVMPLPMNWBH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Bupleurum chinenseLOTUS Database
Fusarium poaeLOTUS Database
Glycyrrhiza glabraLOTUS Database
Mangifera indicaLOTUS Database
Polygala senegaLOTUS Database
Prunus persicaFooDB
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
logP1.42ALOGPS
logP1.53ChemAxon
logS-1.3ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity33.85 m³·mol⁻¹ChemAxon
Polarizability14.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031681  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008341  
KNApSAcK IDNot Available
Chemspider ID7456  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7742  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available