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Showing NP-Card for 5-hydroxy-6-methyl-5,6-dihydropyran-2-one (NP0282259)

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Record Information
Version1.0
Created at2022-09-09 09:01:21 UTC
Updated at2022-09-09 09:01:21 UTC
NP-MRD IDNP0282259
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-hydroxy-6-methyl-5,6-dihydropyran-2-one
DescriptionOsmundalactone belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. Osmundalactone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Osmundalactone has been detected, but not quantified in, root vegetables. 5-hydroxy-6-methyl-5,6-dihydropyran-2-one is found in Tapinella atrotomentosa. This could make osmundalactone a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0282259 (5-hydroxy-6-methyl-5,6-dihydropyran-2-one)


  Mrv0541 05061305522D          

  9  9  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  4  1  0  0  0  0
  9  6  1  0  0  0  0
M  END
Download

3D MOL for NP0282259 (5-hydroxy-6-methyl-5,6-dihydropyran-2-one)

     RDKit          3D

 17 17  0  0  0  0  0  0  0  0999 V2000
   -2.0908    0.7053   -0.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6273    0.4738    0.2907 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1191    1.4647   -0.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5177    1.2910   -0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2920    2.2729   -0.5714 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0998   -0.0427   -0.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2537   -1.0509   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2071   -0.9231   -0.1585 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6928   -1.8010    0.8152 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6599   -0.2503    0.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5269    1.4538    0.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1526    1.0390   -1.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4590    0.5986    1.3732 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -0.2052   -0.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7052   -2.0386   -0.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7147   -1.1766   -1.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0265   -1.8107    1.5592 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  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8  2  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  1
  6 14  1  0
  7 15  1  0
  8 16  1  6
  9 17  1  0
M  END
Download

3D SDF for NP0282259 (5-hydroxy-6-methyl-5,6-dihydropyran-2-one)


  Mrv0541 05061305522D          

  9  9  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  4  1  0  0  0  0
  9  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0282259

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(=O)C=CC1O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O3/c1-4-5(7)2-3-6(8)9-4/h2-5,7H,1H3

> <INCHI_KEY>
TVDPVFPVOHCHQM-UHFFFAOYSA-N

> <FORMULA>
C6H8O3

> <MOLECULAR_WEIGHT>
128.1259

> <EXACT_MASS>
128.047344122

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
12.148069435355406

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
-0.02

> <JCHEM_LOGP>
0.32285567133333304

> <ALOGPS_LOGS>
0.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.748519596377157

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3461814222468567

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
31.6287

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.20e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-6-methyl-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0282259 (5-hydroxy-6-methyl-5,6-dihydropyran-2-one)

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PDB for NP0282259 (5-hydroxy-6-methyl-5,6-dihydropyran-2-one)
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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    3    5                                                       
CONECT    3    2    6                                                       
CONECT    4    1    5    9                                                  
CONECT    5    2    4    7                                                  
CONECT    6    3    8    9                                                  
CONECT    7    5                                                            
CONECT    8    6                                                            
CONECT    9    4    6                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END

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3D PDB for NP0282259 (5-hydroxy-6-methyl-5,6-dihydropyran-2-one)
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SMILES for NP0282259 (5-hydroxy-6-methyl-5,6-dihydropyran-2-one)
CC1OC(=O)C=CC1O
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INCHI for NP0282259 (5-hydroxy-6-methyl-5,6-dihydropyran-2-one)
InChI=1S/C6H8O3/c1-4-5(7)2-3-6(8)9-4/h2-5,7H,1H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC6H8O3
Average Mass128.1259 Da
Monoisotopic Mass128.04734 Da
IUPAC Name5-hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-one
Traditional Name5-hydroxy-6-methyl-5,6-dihydropyran-2-one
CAS Registry NumberNot Available
SMILES
CC1OC(=O)C=CC1O
InChI Identifier
InChI=1S/C6H8O3/c1-4-5(7)2-3-6(8)9-4/h2-5,7H,1H3
InChI KeyTVDPVFPVOHCHQM-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Tapinella atrotomentosaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrans  
Sub ClassPyranones and derivatives  
Direct ParentDihydropyranones  
Alternative Parents
Substituents
  • Dihydropyranone
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Oxacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • 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
logP-0.02ALOGPS
logP0.32ChemAxon
logS0.23ALOGPS
pKa (Strongest Acidic)13.75ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity31.63 m³·mol⁻¹ChemAxon
Polarizability12.15 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031303  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003355  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12374456  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]