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Showing NP-Card for gamma-Thujaplicin (NP0051759)

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Record Information
Version2.0
Created at2022-04-27 23:00:12 UTC
Updated at2022-04-27 23:00:12 UTC
NP-MRD IDNP0051759
Secondary Accession NumbersNone
Natural Product Identification
Common Namegamma-Thujaplicin
Description2-Hydroxy-5-(propan-2-yl)cyclohepta-2,4,6-trien-1-one, also known as 5-isopropyltropolone, belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2. gamma-Thujaplicin is found in Calocedrus decurrens, Cupressus abramisiana, Cupressus lusitanica , Cupressus sargentii, Cupressus stephensonii, Cupressus macrocarpa, Juniperus taiwaniana, Tetraclinis articulata, Thuja occidentalis, Thuja plicata and Thujopsis dolabrata. 2-Hydroxy-5-(propan-2-yl)cyclohepta-2,4,6-trien-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0051759 (gamma-Thujaplicin)


  Mrv1533004191519582D          

 12 12  0  0  0  0            999 V2000
    0.1421    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    2.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5710    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    1.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5999    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6270   -1.1874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0861   -1.1874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0703    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    1.0053    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
M  END
Download

3D MOL for NP0051759 (gamma-Thujaplicin)

     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
   -2.2226   -0.6549    1.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6997   -0.7156   -0.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6100    0.0510   -1.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2968   -0.1991   -0.2210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6609   -1.0712   -0.6853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0428   -1.0005   -0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8581   -0.0331   -0.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2097   -0.3434    0.0702 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4159    1.2058    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3344    1.9827    0.6987 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1427    1.7313    0.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0787    1.1110    0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7227    0.3343    1.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5058   -0.9222    2.0678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0619   -1.4048    1.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7276   -1.7753   -0.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2017   -0.0967   -2.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6585    1.1215   -0.8195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6151   -0.3978   -0.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2553   -1.9640   -1.1573 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5996   -1.7914   -1.1219 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7882    0.3752    0.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0699    2.7663    0.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9762    1.6910    0.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12  4  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  5 20  1  0
  6 21  1  0
  8 22  1  0
 11 23  1  0
 12 24  1  0
M  END
Download

3D SDF for NP0051759 (gamma-Thujaplicin)


  Mrv1533004191519582D          

 12 12  0  0  0  0            999 V2000
    0.1421    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    2.1882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5710    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8566    1.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5999    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7834    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2691   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6270   -1.1874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4441   -0.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0861   -1.1874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0703    0.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1133    1.0053    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051759

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC=C(O)C(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O2/c1-7(2)8-3-5-9(11)10(12)6-4-8/h3-7H,1-2H3,(H,11,12)

> <INCHI_KEY>
WKEWHSLZDDZONF-UHFFFAOYSA-N

> <FORMULA>
C10H12O2

> <MOLECULAR_WEIGHT>
164.204

> <EXACT_MASS>
164.083729626

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
17.938523665173925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-5-(propan-2-yl)cyclohepta-2,4,6-trien-1-one

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
2.0624462706666673

> <ALOGPS_LOGS>
-2.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.434863155601219

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7266508557400266

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
51.5506

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α thujaplicin

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0051759 (gamma-Thujaplicin)

Download
PDB for NP0051759 (gamma-Thujaplicin)
HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       0.265   4.855   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.599   4.085   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.933   4.855   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.599   2.545   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.986   1.876   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.329   0.375   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.369  -0.829   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.037  -2.216   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.829  -0.829   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.161  -2.216   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.131   0.375   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.211   1.876   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11    4                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0051759 (gamma-Thujaplicin)
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SMILES for NP0051759 (gamma-Thujaplicin)
CC(C)C1=CC=C(O)C(=O)C=C1
Download
INCHI for NP0051759 (gamma-Thujaplicin)
InChI=1S/C10H12O2/c1-7(2)8-3-5-9(11)10(12)6-4-8/h3-7H,1-2H3,(H,11,12)
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View in JSmol
Synonyms
ValueSource
5-IsopropyltropoloneKegg
g-THUJAPLICINGenerator
γ-thujaplicinGenerator
2-Hydroxy-5-isopropyl- 2,4,6-cycloheptatrienoneMeSH
Chemical FormulaC10H12O2
Average Mass164.2040 Da
Monoisotopic Mass164.08373 Da
IUPAC Name2-hydroxy-5-(propan-2-yl)cyclohepta-2,4,6-trien-1-one
Traditional Nameα thujaplicin
CAS Registry NumberNot Available
SMILES
CC(C)C1=CC=C(O)C(=O)C=C1
InChI Identifier
InChI=1S/C10H12O2/c1-7(2)8-3-5-9(11)10(12)6-4-8/h3-7H,1-2H3,(H,11,12)
InChI KeyWKEWHSLZDDZONF-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
Calocedrus decurrensLOTUS Database
Cupressus abramisianaPlant
Cupressus lusitanicaPlant
Cupressus sargentiiPlant
Cupressus stephensoniiPlant
Hesperocyparis macrocarpaPlant
Juniperus taiwanianaPlant
Tetraclinis articulataPlant
Thuja occidentalisLOTUS Database
Thuja plicataPlant
Thujopsis dolabrataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2.
KingdomOrganic compounds  
Super ClassHydrocarbon derivatives  
ClassTropones  
Sub ClassTropolones  
Direct ParentTropolones  
Alternative Parents
Substituents
  • Tropolone
    • 

  • Cyclic ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Organooxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP1.72ALOGPS
logP2.06ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)11.43ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity51.55 m³·mol⁻¹ChemAxon
Polarizability17.94 ųChemAxon
Number of Rings1ChemAxon
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 IDC00003063  
Chemspider IDNot Available
KEGG Compound IDC09905  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available