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Showing NP-Card for 5-methyl-2(5H)-furanone (NP0083818)

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Record Information
Version2.0
Created at2022-04-29 04:44:42 UTC
Updated at2022-04-29 04:44:42 UTC
NP-MRD IDNP0083818
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-methyl-2(5H)-furanone
Description5-Methyl-2(3H)-furanone, also known as alpha,beta-angelica lactone or b-angelicalacton, belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom. 5-Methyl-2(3H)-furanone is an extremely weak basic (essentially neutral) compound (based on its pKa). 5-Methyl-2(3H)-furanone is a sweet, coumarin, and nutty tasting compound. Outside of the human body, 5-Methyl-2(3H)-furanone has been detected, but not quantified in, evergreen blackberries. 5-methyl-2(5H)-furanone is found in Coffea arabica . This could make 5-methyl-2(3H)-furanone a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0083818 (5-methyl-2(5H)-furanone)


  Mrv0541 02241218392D          

  7  7  0  0  0  0            999 V2000
    1.4021   -0.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5771   -0.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821   -0.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -0.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    0.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4021    0.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821    0.5358    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
  2  7  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
M  END
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3D MOL for NP0083818 (5-methyl-2(5H)-furanone)

     RDKit          3D

 13 13  0  0  0  0  0  0  0  0999 V2000
    1.6386   -0.3166    0.3851 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5359    0.0424   -0.5919 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3531    0.9969    0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5686    0.5034    0.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5777   -0.8132   -0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5710   -1.5856   -0.4580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3034   -1.0537   -0.8611 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273    0.2916    1.2962 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6168   -0.1812   -0.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5153   -1.3739    0.7005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9399    0.4684   -1.5319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0844    1.9976    0.4960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4155    1.0240    0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  7  1  0
  7  5  1  0
  5  6  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  6
  4 13  1  0
  3 12  1  0
M  END
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3D SDF for NP0083818 (5-methyl-2(5H)-furanone)


  Mrv0541 02241218392D          

  7  7  0  0  0  0            999 V2000
    1.4021   -0.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5771   -0.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821   -0.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -0.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    0.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4021    0.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0821    0.5358    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
  2  7  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083818

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C5H6O2/c1-4-2-3-5(6)7-4/h2-4H,1H3

> <INCHI_KEY>
BGLUXFNVVSVEET-UHFFFAOYSA-N

> <FORMULA>
C5H6O2

> <MOLECULAR_WEIGHT>
98.0999

> <EXACT_MASS>
98.036779436

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
9.440003818526934

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methyl-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
0.53

> <JCHEM_LOGP>
0.9531906133333332

> <ALOGPS_LOGS>
0.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.603358244772529

> <JCHEM_PKA_STRONGEST_BASIC>
-6.818888195642315

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
25.666200000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.00e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α,β-angelica lactone

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0083818 (5-methyl-2(5H)-furanone)

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PDB for NP0083818 (5-methyl-2(5H)-furanone)
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       2.617  -0.230   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.077  -0.230   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.153  -1.462   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.385  -1.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.385   0.538   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.617   1.462   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.153   1.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    2    5                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END

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3D PDB for NP0083818 (5-methyl-2(5H)-furanone)
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SMILES for NP0083818 (5-methyl-2(5H)-furanone)
CC1OC(=O)C=C1
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INCHI for NP0083818 (5-methyl-2(5H)-furanone)
InChI=1S/C5H6O2/c1-4-2-3-5(6)7-4/h2-4H,1H3
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Synonyms
ValueSource
2-Penten-4-olideChEBI
4-Hydroxy-2-pentenoic acid gamma-lactoneChEBI
4-Hydroxypent-2-enoic acid lactoneChEBI
5-Methyl-2(5H)-furanoneChEBI
alpha,beta-Angelica lactoneChEBI
beta-AngelicalactonChEBI
beta-AngelicalactoneChEBI
Delta(1)-Angelica lactoneChEBI
gamma-Methyl-alpha,beta-crotonolactoneChEBI
4-Hydroxy-2-pentenoate g-lactoneGenerator
4-Hydroxy-2-pentenoate gamma-lactoneGenerator
4-Hydroxy-2-pentenoate γ-lactoneGenerator
4-Hydroxy-2-pentenoic acid g-lactoneGenerator
4-Hydroxy-2-pentenoic acid γ-lactoneGenerator
4-Hydroxypent-2-enoate lactoneGenerator
a,b-Angelica lactoneGenerator
Α,β-angelica lactoneGenerator
b-AngelicalactonGenerator
Β-angelicalactonGenerator
b-AngelicalactoneGenerator
Β-angelicalactoneGenerator
Δ(1)-angelica lactoneGenerator
g-Methyl-a,b-crotonolactoneGenerator
Γ-methyl-α,β-crotonolactoneGenerator
2,3-Dihydro-5-methyl-2-furanoneHMDB
3-Pentenoic acid, 4-hydroxy-, gamma-lactoneHMDB
3-Pentenoic acid, 4-hydroxy-, laquo gammaraquo -lactoneHMDB
3-PENTENOIC ACID,4-hydroxy,lactone alpha-angelica-lactoneHMDB
4-Hydroxy-3-pentenoic acid g-lactoneHMDB
4-Hydroxy-3-pentenoic acid gamma-lactoneHMDB
4-Hydroxy-3-pentenoic acid lactoneHMDB
4-Hydroxy-3-pentenoic acid laquo gammaraquo -lactoneHMDB
4-Hydroxy-3-pentenoic acid, gamma-lactoneHMDB
4-Hydroxypent-3-enoic acid lactoneHMDB
5-Methyl-2(3H)-furanone (alpha -angelicalactone)HMDB
5-Methylfuran-2(3H)-oneHMDB
a-Angelica lactoneHMDB
alpha(alpha-Angelica lactoneHMDB
alpha(beta,gamma Or delta2)-angelica lactoneHMDB
alpha-Angelic lactoneHMDB
alpha-Angelica lactoneHMDB
alpha-AngelicalactonHMDB
alpha-AngelicalactoneHMDB
Angelic lactoneHMDB
Angelica lactoneHMDB
beta,gamma-Angelica lactoneHMDB
beta,Laquo gammaraquo -angelica lactoneHMDB
D2-Angelica lactoneHMDB
delta(2)-Angelica lactoneHMDB
FEMA 3293HMDB
gamma-Methyl-beta,gamma-crotonolactoneHMDB
Laquo deltaraquo 2-angelica lactoneHMDB
PENTEN-3-OIC ACID, 4-hydroxy-, gamma-lactoneHMDB
Penten-3-Oic acid, 4-hydroxy-, laquo gammaraquo -lactoneHMDB
b-Angelica lactoneGenerator
Β-angelica lactoneGenerator
Angelica lactone, (alpha)-isomerMeSH
Angelica lactone, (beta)-isomerMeSH
Chemical FormulaC5H6O2
Average Mass98.0999 Da
Monoisotopic Mass98.03678 Da
IUPAC Name5-methyl-2,5-dihydrofuran-2-one
Traditional Nameα,β-angelica lactone
CAS Registry NumberNot Available
SMILES
CC1OC(=O)C=C1
InChI Identifier
InChI=1S/C5H6O2/c1-4-2-3-5(6)7-4/h2-4H,1H3
InChI KeyBGLUXFNVVSVEET-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 arabica L.Plant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as butenolides. These are dihydrofurans with a carbonyl group at the C2 carbon atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDihydrofurans  
Sub ClassFuranones  
Direct ParentButenolides  
Alternative Parents
Substituents
  • 2-furanone
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Lactone
    • 

  • 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
logP0.53ALOGPS
logP0.95ChemAxon
logS0.01ALOGPS
pKa (Strongest Acidic)7.6ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.67 m³·mol⁻¹ChemAxon
Polarizability9.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029609  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000776  
KNApSAcK IDNot Available
Chemspider ID11070  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11558  
PDB IDNot Available
ChEBI ID36436  
Good Scents IDNot Available
References
General ReferencesNot Available