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Showing NP-Card for beta-Thujaplicin (NP0051758)

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Record Information
Version2.0
Created at2022-04-27 23:00:10 UTC
Updated at2022-04-27 23:00:10 UTC
NP-MRD IDNP0051758
Secondary Accession NumbersNone
Natural Product Identification
Common Namebeta-Thujaplicin
DescriptionBeta-Thujaplicin, also known as hinokitiol or β-thujaplicin, belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2. A monoterpenoid that is cyclohepta-2,4,6-trien-1-one substituted by a hydroxy group at position 2 and an isopropyl group at position 4. Beta-Thujaplicin is an extremely weak basic (essentially neutral) compound (based on its pKa). Beta-Thujaplicin is a phenolic and woody tasting compound. Outside of the human body, beta-Thujaplicin has been detected, but not quantified in, fruits. beta-Thujaplicin is found in Calocedrus formosana, Chamaecyparis obtusa, Cupressus abramisiana, Cupressus abramsiana, Cupressus lusitanica , Cupressus sargentii, Cupressus tricuspidata, Cupressus macrocarpa, Juniperus communis , Juniperus conferta, Juniperus taiwaniana, Thuja occidentalis, Thuja plicata and Thujopsis dolabrata. beta-Thujaplicin was first documented in 1948 (PMID: 18118412). This could make beta-thujaplicin a potential biomarker for the consumption of these foods (PMID: 10973816) (PMID: 15917561) (PMID: 17927050) (PMID: 18379073) (PMID: 23312825) (PMID: 12554707).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0051758 (beta-Thujaplicin)


  Mrv0541 05061308182D          

 12 12  0  0  0  0            999 V2000
    1.5710    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1421    2.6007    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
    1.5999    1.0053    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
    0.1133    1.0053    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
    0.8566    1.3632    0.0000 C   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
   -0.0703    0.2009    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
   -0.8746    0.0174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
M  END
Download

3D MOL for NP0051758 (beta-Thujaplicin)

     RDKit          3D

 24 24  0  0  0  0  0  0  0  0999 V2000
   -2.3346   -0.1414   -1.2125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7181   -0.5599    0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4774    0.0231    1.2748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3091   -0.1615    0.0954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0193    1.1813    0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2181    1.7756    0.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4892    1.2197   -0.0231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8297   -0.1038   -0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1864   -0.3905   -0.3450 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9400   -1.1609   -0.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4692   -2.2612   -0.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5947   -1.1982    0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5702    0.0328   -2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8905    0.7977   -1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0168   -0.9448   -1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8185   -1.6612    0.1650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7648    1.0762    1.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3289   -0.6349    1.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7801    0.0167    2.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8472    1.8560   -0.1590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1749    2.8314    0.4359 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3068    1.9336   -0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4652   -1.3555   -0.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2013   -2.1702    0.4987 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 12  2  0
 12 10  1  0
 10 11  2  0
 10  8  1  0
  8  9  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  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
 12 24  1  0
  9 23  1  0
  7 22  1  0
  6 21  1  0
  5 20  1  0
M  END
Download

3D SDF for NP0051758 (beta-Thujaplicin)


  Mrv0541 05061308182D          

 12 12  0  0  0  0            999 V2000
    1.5710    2.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1421    2.6007    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
    1.5999    1.0053    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
    0.1133    1.0053    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
    0.8566    1.3632    0.0000 C   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
   -0.0703    0.2009    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
   -0.8746    0.0174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  4  1  0  0  0  0
  8  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051758

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
FUWUEFKEXZQKKA-UHFFFAOYSA-N

> <FORMULA>
C10H12O2

> <MOLECULAR_WEIGHT>
164.2011

> <EXACT_MASS>
164.083729628

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
17.926332098238966

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.80

> <JCHEM_LOGP>
2.0624462706666673

> <ALOGPS_LOGS>
-2.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.438615192611637

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7250097147516685

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
51.5506

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hinokitiol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0051758 (beta-Thujaplicin)

Download
PDB for NP0051758 (beta-Thujaplicin)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.933   4.855   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.265   4.855   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.329   0.375   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.986   1.877   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.369  -0.829   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.211   1.877   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.599   4.085   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.599   2.545   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.829  -0.829   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.131   0.375   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.161  -2.216   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.633   0.032   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    4    5                                                       
CONECT    4    3    8                                                       
CONECT    5    3    9                                                       
CONECT    6    8   10                                                       
CONECT    7    1    2    8                                                  
CONECT    8    4    6    7                                                  
CONECT    9    5   10   11                                                  
CONECT   10    6    9   12                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

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3D PDB for NP0051758 (beta-Thujaplicin)
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SMILES for NP0051758 (beta-Thujaplicin)
CC(C)C1=CC(=O)C(O)=CC=C1
Download
INCHI for NP0051758 (beta-Thujaplicin)
InChI=1S/C10H12O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-7H,1-2H3,(H,11,12)
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View in JSmol
Synonyms
ValueSource
2-Hydroxy-4-isopropyl-cyclohepta2,4,6-trien-1-oneChEBI
4-IsopropyltropoloneChEBI
HinokitiolChEBI
b-ThujaplicinGenerator
Β-thujaplicinGenerator
2-Hydroxy-4(6)-(1-methylethyl)-2,4,6-cycloheptatrien-1-one, 9ciHMDB
2-Hydroxy-4-(1-methylethyl)-2,4,6-cycloheptatrien-1-oneHMDB
2-Hydroxy-4-isopropyl- 2,4,6-cycloheptatriene-1-oneHMDB
2-Hydroxy-4-isopropyl-2,4, 6-cycloheptatrien-1-oneHMDB
2-Hydroxy-4-isopropyl-2,4,6-cyclohepta-2,4,6-trien-1-oneHMDB
2-Hydroxy-4-isopropyl-2,4,6-cycloheptatrien-1-oneHMDB
2-Hydroxy-4-isopropylcyclohepta-2,4,6-trien-1-oneHMDB
4(6)-IsopropyltropoloneHMDB
4-Isopropyl-tropoloneHMDB
alpha-ThujaplicinHMDB
beta -IsopropyltropolonHMDB
beta -ThujaplicinHMDB
beta -ThujaplicineHMDB
beta-IsopropyltropolonHMDB
beta-IsopropyltropoloneHMDB
beta-ThujaplicineHMDB
Hinokitiol 4-isopropyltropoloneHMDB
HinokitolHMDB
IsopropyltropoloneHMDB
Thujaplicin, betaHMDB
beta-Thujaplicin, sodium saltHMDB
Chemical FormulaC10H12O2
Average Mass164.2011 Da
Monoisotopic Mass164.08373 Da
IUPAC Name2-hydroxy-6-(propan-2-yl)cyclohepta-2,4,6-trien-1-one
Traditional Namehinokitiol
CAS Registry NumberNot Available
SMILES
CC(C)C1=CC(=O)C(O)=CC=C1
InChI Identifier
InChI=1S/C10H12O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-7H,1-2H3,(H,11,12)
InChI KeyFUWUEFKEXZQKKA-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 formosanaLOTUS Database
Chamaecyparis obtusaLOTUS Database
Cupressus abramisianaPlant
Cupressus abramsianaPlant
Cupressus lusitanicaPlant
Cupressus sargentiiPlant
Cupressus tricuspidataPlant
Hesperocyparis macrocarpaPlant
Juniperus communisPlant
Juniperus confertaPlant
Juniperus taiwanianaPlant
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
logP1.8ALOGPS
logP2.06ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)11.44ChemAxon
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
Polarizability17.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035213  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013860  
KNApSAcK IDC00003062  
Chemspider ID3485  
KEGG Compound IDC09904  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHinokitiol  
METLIN IDNot Available
PubChem Compound3611  
PDB IDNot Available
ChEBI ID10447  
Good Scents IDNot Available
References
General References
  1. Suzuki H, Ueda T, Juranek I, Yamamoto S, Katoh T, Node M, Suzuki T: Hinokitiol, a selective inhibitor of the platelet-type isozyme of arachidonate 12-lipoxygenase. Biochem Biophys Res Commun. 2000 Sep 7;275(3):885-9. doi: 10.1006/bbrc.2000.3390. [PubMed:10973816  ] 
  2. Yamano H, Yamazaki T, Sato K, Shiga S, Hagiwara T, Ouchi K, Kishimoto T: In vitro inhibitory effects of hinokitiol on proliferation of Chlamydia trachomatis. Antimicrob Agents Chemother. 2005 Jun;49(6):2519-21. doi: 10.1128/AAC.49.6.2519-2521.2005. [PubMed:15917561  ] 
  3. Morita Y, Sakagami Y, Okabe T, Ohe T, Inamori Y, Ishida N: The mechanism of the bactericidal activity of hinokitiol. Biocontrol Sci. 2007 Sep;12(3):101-10. doi: 10.4265/bio.12.101. [PubMed:17927050  ] 
  4. ANDERSON AB, GRIPENBERG J: Antibiotic substances from the heart wood of Thuja plicata D. Don; the constitution of beta-thujaplicin. Acta Chem Scand. 1948;2(8):644-50. doi: 10.3891/acta.chem.scand.02-0644. [PubMed:18118412  ] 
  5. Komaki N, Watanabe T, Ogasawara A, Sato N, Mikami T, Matsumoto T: Antifungal mechanism of hinokitiol against Candida albicans. Biol Pharm Bull. 2008 Apr;31(4):735-7. doi: 10.1248/bpb.31.735. [PubMed:18379073  ] 
  6. Shih YH, Chang KW, Hsia SM, Yu CC, Fuh LJ, Chi TY, Shieh TM: In vitro antimicrobial and anticancer potential of hinokitiol against oral pathogens and oral cancer cell lines. Microbiol Res. 2013 Jun 12;168(5):254-62. doi: 10.1016/j.micres.2012.12.007. Epub 2013 Jan 11. [PubMed:23312825  ] 
  7. Zhao J, Sakai K: Multiple signalling pathways mediate fungal elicitor-induced beta-thujaplicin biosynthesis in Cupressus lusitanica cell cultures. J Exp Bot. 2003 Feb;54(383):647-56. doi: 10.1093/jxb/erg062. [PubMed:12554707  ]