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Showing NP-Card for α-pyrone (NP0299852)

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Record Information
Version1.0
Created at2022-09-10 11:55:36 UTC
Updated at2022-09-10 11:55:37 UTC
NP-MRD IDNP0299852
Secondary Accession NumbersNone
Natural Product Identification
Common Nameα-pyrone
Description2H-Pyran-2-one, also known as alpha-pyrone or 2-pyrone, belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. α-pyrone is found in Sanguisorba canadensis. It was first documented in 2022 (PMID: 36080412). Based on a literature review a significant number of articles have been published on 2H-Pyran-2-one (PMID: 36013971) (PMID: 35972017) (PMID: 35850257) (PMID: 35760958).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0299852 (α-pyrone)


  Mrv1652309102213552D          

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

3D MOL for NP0299852 (α-pyrone)

     RDKit          3D

 11 11  0  0  0  0  0  0  0  0999 V2000
    2.3874   -1.2570    0.0268 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2121   -0.7696    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1015    0.6067    0.0321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1531    1.1856    0.0166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2231    0.3147   -0.0192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0661   -1.0645   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1548   -1.5423   -0.0225 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0134    1.2120    0.0604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2628    2.2619    0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2097    0.7305   -0.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9544   -1.6781   -0.0669 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  7  1  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  6 11  1  0
  5 10  1  0
  4  9  1  0
  3  8  1  0
M  END
Download

3D SDF for NP0299852 (α-pyrone)


  Mrv1652309102213552D          

  7  7  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 O   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
    1.4289    0.8250    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
    0.7145   -0.4125    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
    0.0000    0.8250    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0299852

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1OC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C5H4O2/c6-5-3-1-2-4-7-5/h1-4H

> <INCHI_KEY>
ZPSJGADGUYYRKE-UHFFFAOYSA-N

> <FORMULA>
C5H4O2

> <MOLECULAR_WEIGHT>
96.085

> <EXACT_MASS>
96.021129369

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
8.640136241610273

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2H-pyran-2-one

> <JCHEM_LOGP>
0.7460225053333331

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.914700914697197

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
26.0955

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
α-pyrone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0299852 (α-pyrone)

Download
PDB for NP0299852 (α-pyrone)
HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   2.310   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       2.667  -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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   1.540   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                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END

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3D PDB for NP0299852 (α-pyrone)
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SMILES for NP0299852 (α-pyrone)
O=C1OC=CC=C1
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INCHI for NP0299852 (α-pyrone)
InChI=1S/C5H4O2/c6-5-3-1-2-4-7-5/h1-4H
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View in JSmol
Synonyms
ValueSource
2-oxo-2H-PyranChEBI
2-PyranoneChEBI
2-PyroneChEBI
5-Hydroxy-2,4-pentadienoic acid delta-lactoneChEBI
alpha-PyroneChEBI
CoumalinChEBI
Pyran-2-oneChEBI
5-Hydroxy-2,4-pentadienoate delta-lactoneGenerator
5-Hydroxy-2,4-pentadienoate δ-lactoneGenerator
5-Hydroxy-2,4-pentadienoic acid δ-lactoneGenerator
a-PyroneGenerator
Α-pyroneGenerator
Chemical FormulaC5H4O2
Average Mass96.0850 Da
Monoisotopic Mass96.02113 Da
IUPAC Name2H-pyran-2-one
Traditional Nameα-pyrone
CAS Registry NumberNot Available
SMILES
O=C1OC=CC=C1
InChI Identifier
InChI=1S/C5H4O2/c6-5-3-1-2-4-7-5/h1-4H
InChI KeyZPSJGADGUYYRKE-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
Sanguisorba canadensisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrans  
Sub ClassPyranones and derivatives  
Direct ParentPyranones and derivatives  
Alternative Parents
Substituents
  • Pyranone
    • 

  • Heteroaromatic compound
    • 

  • Lactone
    • 

  • Oxacycle
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic 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
logP0.75ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity26.1 m³·mol⁻¹ChemAxon
Polarizability8.64 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0245765  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00010361  
Chemspider ID61462  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound68154  
PDB IDNot Available
ChEBI ID37965  
Good Scents IDrw1181231  
References
General References
  1. Liu H, An M, Si H, Shan Y, Xu C, Hu G, Xie Y, Liu D, Li S, Qiu R, Zhang C, Wu Y: Identification of Cyclic Dipeptides and a New Compound (6-(5-Hydroxy-6-methylheptyl)-5,6-dihydro-2H-pyran-2-one) Produced by Streptomyces fungicidicus against Alternaria solani. Molecules. 2022 Sep 1;27(17):5649. doi: 10.3390/molecules27175649. [PubMed:36080412  ] 
  2. Dai Z, Gan Y, Zhao P, Li G: Secondary Metabolites from the Endoparasitic Nematophagous Fungus Harposporium anguillulae YMF 1.01751. Microorganisms. 2022 Jul 31;10(8):1553. doi: 10.3390/microorganisms10081553. [PubMed:36013971  ] 
  3. Rapagnani RM, Tonks IA: 3-Ethyl-6-vinyltetrahydro-2H-pyran-2-one (EVP): a versatile CO(2)-derived lactone platform for polymer synthesis. Chem Commun (Camb). 2022 Aug 25;58(69):9586-9593. doi: 10.1039/d2cc03516b. [PubMed:35972017  ] 
  4. Paulose SK, Chakraborty K: Anti-hyperglycemic Delta5 steroids, marginoids A-C from marine veined octopus Amphioctopus marginatus (Octopodidae): Prospective natural leads inhibit serineexopeptidase dipeptidyl peptidase-4. Steroids. 2022 Oct;186:109090. doi: 10.1016/j.steroids.2022.109090. Epub 2022 Jul  16. [PubMed:35850257  ] 
  5. Rapagnani RM, Dunscomb RJ, Fresh AA, Tonks IA: Tunable and recyclable polyesters from CO(2) and butadiene. Nat Chem. 2022 Aug;14(8):877-883. doi: 10.1038/s41557-022-00969-2. Epub 2022 Jun  27. [PubMed:35760958  ] 
  6. LOTUS database [Link]