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Showing NP-Card for Chimaphilin (NP0051594)

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Record Information
Version2.0
Created at2022-04-27 22:54:08 UTC
Updated at2022-04-27 22:54:08 UTC
NP-MRD IDNP0051594
Secondary Accession NumbersNone
Natural Product Identification
Common NameChimaphilin
DescriptionChimaphilin belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). Chimaphilin is found in Chimaphila corymbosa, Chimaphila umbellata , Moneses uniflora, Pyrola americana, Pyrola incarnata, Pyrola japonica , Pyrola media and Pyrola renifolia. Chimaphilin is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0051594 (Chimaphilin)


  Mrv1533004161521322D          

 14 15  0  0  0  0            999 V2000
    0.0000   -1.6500    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   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
Download

3D MOL for NP0051594 (Chimaphilin)

     RDKit          3D

 24 25  0  0  0  0  0  0  0  0999 V2000
    3.8565    0.6696   -0.0485 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5063    0.0573   -0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3779   -1.2357   -0.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0682   -1.8781   -0.4667 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9449   -3.1053   -0.7110 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1614   -1.1025   -0.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4107   -1.6779   -0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5361   -0.8988   -0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4398    0.4326    0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6179    1.3263    0.3475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2000    1.0093    0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0488    0.2394    0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763    0.8127    0.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3812    2.0398    0.3162 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8802    1.2786    0.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6133   -0.1113   -0.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0123    1.3037   -0.9685 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2987   -1.8121   -0.5317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4998   -2.7388   -0.5507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5434   -1.3314   -0.1937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5279    0.7447    0.5326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8136    1.9461   -0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3642    1.9651    1.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0523    2.0667    0.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  4  1  0
  4  5  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 13  1  0
 13 14  2  0
 13 12  1  0
 12 11  2  0
 11  9  1  0
 12  6  1  0
 10 21  1  0
 10 22  1  0
 10 23  1  0
  8 20  1  0
  7 19  1  0
  3 18  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
 11 24  1  0
M  END
Download

3D SDF for NP0051594 (Chimaphilin)


  Mrv1533004161521322D          

 14 15  0  0  0  0            999 V2000
    0.0000   -1.6500    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   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051594

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC=C2C(=O)C=C(C)C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O2/c1-7-3-4-9-10(5-7)12(14)8(2)6-11(9)13/h3-6H,1-2H3

> <INCHI_KEY>
YZACZIYTZCJVSN-UHFFFAOYSA-N

> <FORMULA>
C12H10O2

> <MOLECULAR_WEIGHT>
186.21

> <EXACT_MASS>
186.068079562

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.87903747296246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,7-dimethyl-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
2.4032898293333327

> <ALOGPS_LOGS>
-3.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.082287852441961

> <JCHEM_PKA_STRONGEST_BASIC>
-7.153549289936301

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
55.5815

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.09e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chimaphilin

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0051594 (Chimaphilin)

Download
PDB for NP0051594 (Chimaphilin)
HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   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       1.334  -0.770   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       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12    2   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for NP0051594 (Chimaphilin)
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SMILES for NP0051594 (Chimaphilin)
CC1=CC=C2C(=O)C=C(C)C(=O)C2=C1
Download
INCHI for NP0051594 (Chimaphilin)
InChI=1S/C12H10O2/c1-7-3-4-9-10(5-7)12(14)8(2)6-11(9)13/h3-6H,1-2H3
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View in JSmol
Synonyms
ValueSource
2,7-Dimethyl-1,4-naphthoquinoneMeSH
Chemical FormulaC12H10O2
Average Mass186.2100 Da
Monoisotopic Mass186.06808 Da
IUPAC Name2,7-dimethyl-1,4-dihydronaphthalene-1,4-dione
Traditional Namechimaphilin
CAS Registry NumberNot Available
SMILES
CC1=CC=C2C(=O)C=C(C)C(=O)C2=C1
InChI Identifier
InChI=1S/C12H10O2/c1-7-3-4-9-10(5-7)12(14)8(2)6-11(9)13/h3-6H,1-2H3
InChI KeyYZACZIYTZCJVSN-UHFFFAOYSA-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
Chimaphila corymbosaPlant
Chimaphila umbellataPlant
Moneses unifloraLOTUS Database
Pyrola americanaLOTUS Database
Pyrola incarnataPlant
Pyrola japonicaPlant
Pyrola mediaLOTUS Database
Pyrola renifoliaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassNaphthalenes  
Sub ClassNaphthoquinones  
Direct ParentNaphthoquinones  
Alternative Parents
Substituents
  • Naphthoquinone
    • 

  • Aryl ketone
    • 

  • Quinone
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic 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
logP2.21ALOGPS
logP2.4ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)13.08ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area34.14 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity55.58 m³·mol⁻¹ChemAxon
Polarizability19.88 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002802  
Chemspider IDNot Available
KEGG Compound IDC10310  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101211  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available