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Showing NP-Card for (6s)-2-(hydroxymethyl)-6-methyl-5,6-dihydropyran-4-one (NP0195776)

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Record Information
Version2.0
Created at2022-09-04 13:42:27 UTC
Updated at2022-09-04 13:42:27 UTC
NP-MRD IDNP0195776
Secondary Accession NumbersNone
Natural Product Identification
Common Name(6s)-2-(hydroxymethyl)-6-methyl-5,6-dihydropyran-4-one
DescriptionErinapyrone A 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. (6s)-2-(hydroxymethyl)-6-methyl-5,6-dihydropyran-4-one is found in Hericium erinaceus. Based on a literature review very few articles have been published on Erinapyrone A.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0195776 ((6s)-2-(hydroxymethyl)-6-methyl-5,6-dihydropyran-4-one)


  Mrv1652309042215422D          

 10 10  0  0  1  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  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
    2.1434   -0.4125    0.0000 O   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
   -0.7145   -0.4125    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
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
  2 10  1  0  0  0  0
M  END
Download

3D MOL for NP0195776 ((6s)-2-(hydroxymethyl)-6-methyl-5,6-dihydropyran-4-one)

     RDKit          3D

 20 20  0  0  0  0  0  0  0  0999 V2000
   -2.2245    1.2012    0.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0914    0.2702    0.6170 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3460   -1.1246    0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3508   -1.6314   -0.8128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6693   -2.5044   -1.6585 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9978   -1.0852   -0.7574 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2060    0.1202   -0.2560 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6033    0.6084   -0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0514    0.8896    1.0486 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1173    0.8209    0.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9478    1.6362   -0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3362    1.9814    0.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1435    0.6107    0.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0913    0.2700    1.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3420   -1.1666   -0.3384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4180   -1.8574    1.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8211   -1.6876   -1.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2489   -0.0443   -0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5922    1.5948   -0.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3227    1.0981    1.6665 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
  7 10  1  0
 10  2  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  2 14  1  1
  3 15  1  0
  3 16  1  0
  6 17  1  0
  8 18  1  0
  8 19  1  0
  9 20  1  0
M  END
Download

3D SDF for NP0195776 ((6s)-2-(hydroxymethyl)-6-methyl-5,6-dihydropyran-4-one)


  Mrv1652309042215422D          

 10 10  0  0  1  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  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
    2.1434   -0.4125    0.0000 O   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
   -0.7145   -0.4125    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
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
  2 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195776

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CC(=O)C=C(CO)O1

> <INCHI_IDENTIFIER>
InChI=1S/C7H10O3/c1-5-2-6(9)3-7(4-8)10-5/h3,5,8H,2,4H2,1H3/t5-/m0/s1

> <INCHI_KEY>
FXGUGSUNHREWBM-YFKPBYRVSA-N

> <FORMULA>
C7H10O3

> <MOLECULAR_WEIGHT>
142.154

> <EXACT_MASS>
142.062994182

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.209635236763917

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-6-(hydroxymethyl)-2-methyl-3,4-dihydro-2H-pyran-4-one

> <JCHEM_LOGP>
-0.23466607266666653

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.036024692051832

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.383313960677569

> <JCHEM_PKA_STRONGEST_BASIC>
-3.06847871452724

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
37.4933

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(6S)-2-(hydroxymethyl)-6-methyl-5,6-dihydropyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0195776 ((6s)-2-(hydroxymethyl)-6-methyl-5,6-dihydropyran-4-one)

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PDB for NP0195776 ((6s)-2-(hydroxymethyl)-6-methyl-5,6-dihydropyran-4-one)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+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  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    2                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0195776 ((6s)-2-(hydroxymethyl)-6-methyl-5,6-dihydropyran-4-one)
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SMILES for NP0195776 ((6s)-2-(hydroxymethyl)-6-methyl-5,6-dihydropyran-4-one)
C[C@H]1CC(=O)C=C(CO)O1
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INCHI for NP0195776 ((6s)-2-(hydroxymethyl)-6-methyl-5,6-dihydropyran-4-one)
InChI=1S/C7H10O3/c1-5-2-6(9)3-7(4-8)10-5/h3,5,8H,2,4H2,1H3/t5-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC7H10O3
Average Mass142.1540 Da
Monoisotopic Mass142.06299 Da
IUPAC Name(2S)-6-(hydroxymethyl)-2-methyl-3,4-dihydro-2H-pyran-4-one
Traditional Name(6S)-2-(hydroxymethyl)-6-methyl-5,6-dihydropyran-4-one
CAS Registry NumberNot Available
SMILES
C[C@H]1CC(=O)C=C(CO)O1
InChI Identifier
InChI=1S/C7H10O3/c1-5-2-6(9)3-7(4-8)10-5/h3,5,8H,2,4H2,1H3/t5-/m0/s1
InChI KeyFXGUGSUNHREWBM-YFKPBYRVSA-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
Hericium erinaceusLOTUS 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
    • 

  • Vinylogous ester
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Oxacycle
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • 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-0.23ChemAxon
pKa (Strongest Acidic)14.38ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.49 m³·mol⁻¹ChemAxon
Polarizability14.21 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 IDC00024008  
Chemspider ID8572371  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10396933  
PDB IDNot Available
ChEBI ID184226  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]