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Showing metabocard for beta-Thujaplicin (HMDB0035213)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:09:48 UTC
Update Date2023-02-21 17:24:41 UTC
HMDB IDHMDB0035213
Secondary Accession Numbers
  • HMDB35213
Metabolite 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. beta-Thujaplicin is a phenolic and woody tasting compound. beta-Thujaplicin has been detected, but not quantified in, fruits. This could make beta-thujaplicin a potential biomarker for the consumption of these foods. beta-Thujaplicin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on beta-Thujaplicin.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0035213 (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
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3D MOL for HMDB0035213 (beta-Thujaplicin)

HMDB0035213
     RDKit          3D
beta-Thujaplicin
 24 24  0  0  0  0  0  0  0  0999 V2000
   -2.1903   -0.0547   -1.6004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7128   -0.5401   -0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6443    0.0134    0.7863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2905   -0.1681   -0.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0319    1.1718    0.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2467    1.7825    0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045    1.1966    0.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8480   -0.1377    0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -0.4343    0.3630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9632   -1.1938    0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931   -2.2864    0.7540 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5911   -1.2051    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1290   -0.6134   -1.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4448    1.0206   -1.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763   -0.3313   -2.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8244   -1.6419   -0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3267   -0.1721    1.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7990    1.0790    0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6203   -0.5030    0.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7642    1.8614   -0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2676    2.8576    0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3306    1.8621    0.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5481   -1.3906    0.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1724   -2.1724    0.0485 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12  4  2  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
  7 22  1  0
  9 23  1  0
 12 24  1  0
M  END
Download

3D SDF for HMDB0035213 (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>
HMDB0035213

> <DATABASE_NAME>
hmdb

> <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

$$$$
Download

3D-SDF for HMDB0035213 (beta-Thujaplicin)

HMDB0035213
     RDKit          3D
beta-Thujaplicin
 24 24  0  0  0  0  0  0  0  0999 V2000
   -2.1903   -0.0547   -1.6004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7128   -0.5401   -0.2450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6443    0.0134    0.7863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2905   -0.1681   -0.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0319    1.1718    0.0269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2467    1.7825    0.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045    1.1966    0.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8480   -0.1377    0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2251   -0.4343    0.3630 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9632   -1.1938    0.4350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931   -2.2864    0.7540 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5911   -1.2051    0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1290   -0.6134   -1.8191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4448    1.0206   -1.5984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4763   -0.3313   -2.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8244   -1.6419   -0.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3267   -0.1721    1.8279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7990    1.0790    0.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6203   -0.5030    0.6663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7642    1.8614   -0.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2676    2.8576    0.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3306    1.8621    0.6314 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5481   -1.3906    0.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1724   -2.1724    0.0485 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12  4  2  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
  7 22  1  0
  9 23  1  0
 12 24  1  0
M  END
Download

PDB for HMDB0035213 (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 HMDB0035213 (beta-Thujaplicin)

COMPND    HMDB0035213
HETATM    1  C1  UNL     1      -2.190  -0.055  -1.600  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.713  -0.540  -0.245  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.644   0.013   0.786  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.290  -0.168  -0.010  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.032   1.172   0.027  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.247   1.782   0.269  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.505   1.197   0.446  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.848  -0.138   0.416  1.00  0.00           C  
HETATM    9  O1  UNL     1       4.225  -0.434   0.363  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.963  -1.194   0.435  1.00  0.00           C  
HETATM   11  O2  UNL     1       2.493  -2.286   0.754  1.00  0.00           O  
HETATM   12  C10 UNL     1       0.591  -1.205   0.152  1.00  0.00           C  
HETATM   13  H1  UNL     1      -3.129  -0.613  -1.819  1.00  0.00           H  
HETATM   14  H2  UNL     1      -2.445   1.021  -1.598  1.00  0.00           H  
HETATM   15  H3  UNL     1      -1.476  -0.331  -2.408  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.824  -1.642  -0.250  1.00  0.00           H  
HETATM   17  H5  UNL     1      -2.327  -0.172   1.828  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.799   1.079   0.589  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.620  -0.503   0.666  1.00  0.00           H  
HETATM   20  H8  UNL     1      -0.764   1.861  -0.157  1.00  0.00           H  
HETATM   21  H9  UNL     1       1.268   2.858   0.337  1.00  0.00           H  
HETATM   22  H10 UNL     1       3.331   1.862   0.631  1.00  0.00           H  
HETATM   23  H11 UNL     1       4.548  -1.391   0.339  1.00  0.00           H  
HETATM   24  H12 UNL     1       0.172  -2.172   0.049  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    4   16
CONECT    3   17   18   19
CONECT    4    5   12   12
CONECT    5    6    6   20
CONECT    6    7   21
CONECT    7    8    8   22
CONECT    8    9   10
CONECT    9   23
CONECT   10   11   11   12
CONECT   12   24
END
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SMILES for HMDB0035213 (beta-Thujaplicin)

CC(C)C1=CC(=O)C(O)=CC=C1
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INCHI for HMDB0035213 (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 JSmolView Stereo Labels
Synonyms
Chemical FormulaC10H12O2
Average Molecular Weight164.2011
Monoisotopic Molecular Weight164.083729628
IUPAC Name2-hydroxy-6-(propan-2-yl)cyclohepta-2,4,6-trien-1-one
Traditional Namehinokitiol
CAS Registry Number499-44-5
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
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
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point52 - 52.5 °CNot Available
Boiling Point140.00 °C. @ 10.00 mm HgThe Good Scents Company Information System
Water Solubility1.2 mg/mL at 25 °CNot Available
LogP1.137 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1044801
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:12554707 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .