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Showing NP-Card for Dihydro-3-methyl-2(3H)-furanone (NP0084567)

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Record Information
Version2.0
Created at2022-04-29 05:16:09 UTC
Updated at2022-04-29 05:16:09 UTC
NP-MRD IDNP0084567
Secondary Accession NumbersNone
Natural Product Identification
Common NameDihydro-3-methyl-2(3H)-furanone
DescriptionDihydro-3-methyl-2(3H)-furanone, also known as gama-valerolactone or 2-methyl-4-butanolide, 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. Dihydro-3-methyl-2(3H)-furanone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Dihydro-3-methyl-2(3H)-furanone has been detected, but not quantified in, fruits. Dihydro-3-methyl-2(3H)-furanone is found in Coffea arabica, Lavandula angustifolia and Mangifera indica . This could make dihydro-3-methyl-2(3H)-furanone a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0084567 (Dihydro-3-methyl-2(3H)-furanone)


  Mrv0541 05061308152D          

  7  7  0  0  0  0            999 V2000
   -0.8843    0.8843    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
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   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
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  7  5  1  0  0  0  0
M  END
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3D MOL for NP0084567 (Dihydro-3-methyl-2(3H)-furanone)

     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
   -1.5617   -0.3668    0.4419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5316    0.1016   -0.5604 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7208   -0.7367   -0.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5819   -0.0126    0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1082    1.3240    0.5408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0526    1.4542   -0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6163    2.5292   -0.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1075   -0.7065    1.3891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2664    0.4791    0.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0628   -1.2502   -0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9620    0.0889   -1.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4980   -1.7743   -0.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1503   -0.7253   -1.5407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4603   -0.4549    1.4745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6414    0.0503    0.1496 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  2  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  6
  3 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
M  END
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3D SDF for NP0084567 (Dihydro-3-methyl-2(3H)-furanone)


  Mrv0541 05061308152D          

  7  7  0  0  0  0            999 V2000
   -0.8843    0.8843    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
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   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
    0.5678    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  7  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084567

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCOC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O2/c1-4-2-3-7-5(4)6/h4H,2-3H2,1H3

> <INCHI_KEY>
QGLBZNZGBLRJGS-UHFFFAOYSA-N

> <FORMULA>
C5H8O2

> <MOLECULAR_WEIGHT>
100.1158

> <EXACT_MASS>
100.0524295

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
10.094021561867002

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-methyloxolan-2-one

> <ALOGPS_LOGP>
0.36

> <JCHEM_LOGP>
0.6925375840000001

> <ALOGPS_LOGS>
-0.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.069527996406953

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
24.882600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.31e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methylbutyrolactone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0084567 (Dihydro-3-methyl-2(3H)-furanone)

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PDB for NP0084567 (Dihydro-3-methyl-2(3H)-furanone)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.651   1.651   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.060   3.620   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.306   1.175   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    3    4                                                       
CONECT    3    2    7                                                       
CONECT    4    1    2    5                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    3    5                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END

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3D PDB for NP0084567 (Dihydro-3-methyl-2(3H)-furanone)
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SMILES for NP0084567 (Dihydro-3-methyl-2(3H)-furanone)
CC1CCOC1=O
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INCHI for NP0084567 (Dihydro-3-methyl-2(3H)-furanone)
InChI=1S/C5H8O2/c1-4-2-3-7-5(4)6/h4H,2-3H2,1H3
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View in JSmol
Synonyms
ValueSource
Gama-valerolactoneHMDB
2-Methyl-4-butanolideHMDB
2-Methyl-laquo gammaraquo -butyrolactoneHMDB
2-MethylbutanolideHMDB
3-Methyldihydro-2(3H)-furanoneHMDB
3-Methyldihydrofuran-2(3H)-oneHMDB
4,5-Dihydro-3-methyl-2(3H)-furanoneHMDB
4-Hydroxy-2-methylbutanoic acid lactoneHMDB
4-Hydroxy-2-methylbutyric acid lactoneHMDB
a-Methyl-g-butyrolactoneHMDB
alpha -Methyl-alpha -methylbutyrolactoneHMDB
alpha -Methyl-laquo gammaraquo -butyrolactoneHMDB
alpha -MethylbutyrolactoneHMDB
alpha-Methyl-gamma-butyrolactoneHMDB
2-Methyl-g-butyrolactoneGenerator
2-Methyl-γ-butyrolactoneGenerator
Chemical FormulaC5H8O2
Average Mass100.1158 Da
Monoisotopic Mass100.05243 Da
IUPAC Name3-methyloxolan-2-one
Traditional Name3-methylbutyrolactone
CAS Registry NumberNot Available
SMILES
CC1CCOC1=O
InChI Identifier
InChI=1S/C5H8O2/c1-4-2-3-7-5(4)6/h4H,2-3H2,1H3
InChI KeyQGLBZNZGBLRJGS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Coffea arabicaLOTUS Database
Lavandula angustifoliaLOTUS Database
Mangifera indicaPlant
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 DescriptorsNot Available
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
logP0.36ALOGPS
logP0.69ChemAxon
logS-0.03ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity24.88 m³·mol⁻¹ChemAxon
Polarizability10.09 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035143  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013779  
KNApSAcK IDNot Available
Chemspider ID88786  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound98323  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available