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Showing NP-Card for Panepoxydione (NP0078649)

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Record Information
Version2.0
Created at2022-04-28 23:40:53 UTC
Updated at2022-04-28 23:40:53 UTC
NP-MRD IDNP0078649
Secondary Accession NumbersNone
Natural Product Identification
Common NamePanepoxydione
DescriptionPanepoxydione belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. Panepoxydione is found in Lentinus connatus and Lentinus connatus BCC8996. It was first documented in 2005 (PMID: 16309322). Based on a literature review very few articles have been published on panepoxydione (PMID: 26434125).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0078649 (Panepoxydione)


  Mrv1652304292201402D          

 15 16  0  0  1  0            999 V2000
    0.4763   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4763   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1908    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6197   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0487   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7631   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0487   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  2 15  1  1  0  0  0
  1 15  1  1  0  0  0
M  END
Download

3D MOL for NP0078649 (Panepoxydione)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
    3.2732   -1.4390   -0.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3677   -0.3211   -0.4216 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7621    0.6035    0.6789 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2251   -0.1603   -1.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3262    0.9440   -0.6799 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1410    1.8000   -1.7774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9668    0.4079   -0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1797   -0.8814   -0.1979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4780   -1.3848    0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6816   -2.6320    0.1478 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4987   -0.4962    0.8279 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1671    0.3274   -0.1236 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2572    0.8844    0.8344 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9983    1.3316    0.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8516    2.5707    0.0270 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3272   -1.1012   -0.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1355   -2.2908   -0.1133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0190   -1.7686   -1.8339 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0043    0.5387    1.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7912    0.3630    1.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7871    1.6407    0.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9504   -0.8319   -1.8495 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7535    1.5553    0.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4740    1.3063   -2.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4110   -1.5622   -0.5104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2077   -0.9619    1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6918    1.5578    1.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14  7  1  0
 13 11  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  1
  6 24  1  0
  8 25  1  0
 11 26  1  1
 13 27  1  1
M  END
Download

3D SDF for NP0078649 (Panepoxydione)


  Mrv1652304292201402D          

 15 16  0  0  1  0            999 V2000
    0.4763   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4763   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1908    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6197   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0487   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7631   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0487   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  2  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  2 15  1  1  0  0  0
  1 15  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0078649

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C[C@@H](O)C1=CC(=O)[C@@H]2O[C@@H]2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O4/c1-5(2)3-7(12)6-4-8(13)10-11(15-10)9(6)14/h3-4,7,10-12H,1-2H3/t7-,10+,11-/m1/s1

> <INCHI_KEY>
SPHYQDXGWOASKY-PPKCKEKNSA-N

> <FORMULA>
C11H12O4

> <MOLECULAR_WEIGHT>
208.213

> <EXACT_MASS>
208.073558866

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.255520514089746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,6R)-3-[(1R)-1-hydroxy-3-methylbut-2-en-1-yl]-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
0.9337243186666665

> <ALOGPS_LOGS>
-0.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.36902980793482

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.982906423137425

> <JCHEM_PKA_STRONGEST_BASIC>
-3.242165553143744

> <JCHEM_POLAR_SURFACE_AREA>
66.89999999999999

> <JCHEM_REFRACTIVITY>
54.04530000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.82e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,6R)-3-[(1R)-1-hydroxy-3-methylbut-2-en-1-yl]-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0078649 (Panepoxydione)

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PDB for NP0078649 (Panepoxydione)
HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       0.889  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.889  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.223   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.223   2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.556  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.556  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.223  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.223  -3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.890  -2.310   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.890  -3.850   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.224  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.558  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.891  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.558  -3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.445  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    7   15                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    2    1                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

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3D PDB for NP0078649 (Panepoxydione)
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SMILES for NP0078649 (Panepoxydione)
CC(C)=C[C@@H](O)C1=CC(=O)[C@@H]2O[C@@H]2C1=O
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INCHI for NP0078649 (Panepoxydione)
InChI=1S/C11H12O4/c1-5(2)3-7(12)6-4-8(13)10-11(15-10)9(6)14/h3-4,7,10-12H,1-2H3/t7-,10+,11-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC11H12O4
Average Mass208.2130 Da
Monoisotopic Mass208.07356 Da
IUPAC Name(1S,6R)-3-[(1R)-1-hydroxy-3-methylbut-2-en-1-yl]-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
Traditional Name(1S,6R)-3-[(1R)-1-hydroxy-3-methylbut-2-en-1-yl]-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
CAS Registry NumberNot Available
SMILES
CC(C)=C[C@@H](O)C1=CC(=O)[C@@H]2O[C@@H]2C1=O
InChI Identifier
InChI=1S/C11H12O4/c1-5(2)3-7(12)6-4-8(13)10-11(15-10)9(6)14/h3-4,7,10-12H,1-2H3/t7-,10+,11-/m1/s1
InChI KeySPHYQDXGWOASKY-PPKCKEKNSA-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
Lentinus connatusLOTUS Database
Lentinus connatus BCC8996Fungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentCyclohexenones  
Alternative Parents
Substituents
  • Cyclohexenone
    • 

  • Secondary alcohol
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Oxirane
    • 

  • Dialkyl ether
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Aldehyde
    • 

  • Alcohol
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP0.48ALOGPS
logP0.93ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)13.98ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.9 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.05 m³·mol⁻¹ChemAxon
Polarizability20.26 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00042825  
Chemspider ID10122982  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11948666  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Rukachaisirikul V, Tansakul C, Saithong S, Pakawatchai C, Isaka M, Suvannakad R: Hirsutane sesquiterpenes from the fungus Lentinus connatus BCC 8996. J Nat Prod. 2005 Nov;68(11):1674-6. doi: 10.1021/np0502286. [PubMed:16309322  ] 
  2. Isaka M, Palasarn S, Sappana M, Srichomthong K, Karunarathna SC, Hyde KD: Prenylhydroquinone-Derived Secondary Metabolites from Cultures of the Basidiomycete Lentinus similis BCC 52578. Nat Prod Commun. 2015 Aug;10(8):1391-3. [PubMed:26434125  ]