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Record Information
Version1.0
Created at2022-09-06 18:31:37 UTC
Updated at2022-09-06 18:31:37 UTC
NP-MRD IDNP0235794
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5s,6r)-5-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. (5s,6r)-5-hydroxy-6-methyl-5,6-dihydropyran-2-one is found in Angiopteris caudatiformis and Tapinella atrotomentosa. It was first documented in 2009 (PMID: 19371069). Based on a literature review a small amount of articles have been published on Osmundalactone (PMID: 32183470) (PMID: 29734648) (PMID: 22863714).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC6H8O3
Average Mass128.1270 Da
Monoisotopic Mass128.04734 Da
IUPAC Name(5S,6R)-5-hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-one
Traditional Name(5S,6R)-5-hydroxy-6-methyl-5,6-dihydropyran-2-one
CAS Registry NumberNot Available
SMILES
C[C@H]1OC(=O)C=C[C@@H]1O
InChI Identifier
InChI=1S/C6H8O3/c1-4-5(7)2-3-6(8)9-4/h2-5,7H,1H3/t4-,5+/m1/s1
InChI KeyTVDPVFPVOHCHQM-UHNVWZDZSA-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
Angiopteris caudatiformisLOTUS Database
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
logP0.32ChemAxon
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 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00048033
Chemspider ID10232880
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12374457
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Lamichhane R, Pandeya PR, Lee KH, Kim SG, Devkota HP, Jung HJ: Anti-Adipogenic and Anti-Inflammatory Activities of (-)-epi-Osmundalactone and Angiopteroside from Angiopteris helferiana C.Presl. Molecules. 2020 Mar 15;25(6). pii: molecules25061337. doi: 10.3390/molecules25061337. [PubMed:32183470 ]
  2. Beni Z, Dekany M, Kovacs B, Csupor-Loffler B, Zomborszki ZP, Kerekes E, Szekeres A, Urban E, Hohmann J, Vanyolos A: Bioactivity-Guided Isolation of Antimicrobial and Antioxidant Metabolites from the Mushroom Tapinella atrotomentosa. Molecules. 2018 May 4;23(5). pii: molecules23051082. doi: 10.3390/molecules23051082. [PubMed:29734648 ]
  3. Ono M, Zhao XY, Kato K, Akita H: The asymmetric syntheses of methyl D-digitoxoside, L-oleandrose and L-cymarose from methyl sorbate, an achiral precursor. Chem Pharm Bull (Tokyo). 2012;60(8):1076-82. doi: 10.1248/cpb.c12-00308. [PubMed:22863714 ]
  4. Yu YM, Yang JS, Peng CZ, Caer V, Cong PZ, Zou ZM, Lu Y, Yang SY, Gu YC: Lactones from Angiopteris caudatiformis. J Nat Prod. 2009 May 22;72(5):921-4. doi: 10.1021/np900027m. [PubMed:19371069 ]
  5. LOTUS database [Link]