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Showing NP-Card for (-)-β-thujone (NP0249599)

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Record Information
Version2.0
Created at2022-09-07 12:12:12 UTC
Updated at2022-09-07 12:12:12 UTC
NP-MRD IDNP0249599
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-β-thujone
Description(-)-3-Thujone, also known as L-isothujone, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. (-)-β-thujone is found in Artemisia gmelinii, Artemisia herba-alba, Teucrium polium and Thymus marschallianus. Thus, (-)-3-thujone is considered to be an isoprenoid lipid molecule (-)-3-Thujone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0249599 ((-)-β-thujone)


  Mrv0541 02241209132D          

 11 12  0  0  1  0            999 V2000
   -0.5992    0.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213    0.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062    0.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569   -0.4506    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1576   -0.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569   -1.2756    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3415   -1.5305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5964   -2.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8264   -0.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6514   -0.8631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415   -0.1956    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
  4  2  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
M  END
Download

3D MOL for NP0249599 ((-)-β-thujone)

     RDKit          3D

 27 28  0  0  0  0  0  0  0  0999 V2000
   -2.4947    0.7390   -1.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6442   -0.4009   -0.5427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3780   -0.9286    0.6549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2991    0.1344   -0.1692 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0579    0.6692    1.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4262    0.8212    1.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0318    1.7778    1.6469 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8952   -0.4535    0.6175 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3227   -0.3753    0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9593   -0.5462   -0.5918 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5365    0.7485   -1.2384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5528    0.4563   -1.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1608    0.9486   -2.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3263    1.6261   -0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5193   -1.1650   -1.3378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7512   -1.4114    1.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1724   -1.6711    0.3597 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9260   -0.0951    1.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5930    1.5985    1.4342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2747   -0.1303    1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7015   -1.2584    1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7178    0.6577    0.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -0.7951   -0.8815 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9455   -1.0576    0.7713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9567   -1.4799   -1.1534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2672    0.6356   -2.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0370    1.6892   -1.0037 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  2  1  6
  4 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
 10  4  1  0
  5  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
 11 26  1  0
 11 27  1  0
 10 25  1  6
  8 21  1  1
  9 22  1  0
  9 23  1  0
  9 24  1  0
  5 19  1  0
  5 20  1  0
M  END
Download

3D SDF for NP0249599 ((-)-β-thujone)


  Mrv0541 02241209132D          

 11 12  0  0  1  0            999 V2000
   -0.5992    0.3893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213    0.3031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062    0.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569   -0.4506    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1576   -0.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569   -1.2756    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3415   -1.5305    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5964   -2.3151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8264   -0.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6514   -0.8631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415   -0.1956    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
  4  2  1  0  0  0  0
  4  5  1  6  0  0  0
  6  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0249599

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@]12C[C@H]1[C@@H](C)C(=O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8+,10-/m1/s1

> <INCHI_KEY>
USMNOWBWPHYOEA-KHQFGBGNSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.2334

> <EXACT_MASS>
152.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.015478521705248

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4R,5S)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
2.2839903843333342

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.422104234360747

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
44.5396

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-β-thujone

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0249599 ((-)-β-thujone)

Download
PDB for NP0249599 ((-)-β-thujone)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.119   0.727   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.413   0.566   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.318   1.812   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.040  -0.841   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.294  -1.611   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.040  -2.381   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.504  -2.857   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.980  -4.322   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.409  -1.611   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.949  -1.611   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.504  -0.365   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6   11                                             
CONECT    5    4    6                                                       
CONECT    6    5    4    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0249599 ((-)-β-thujone)
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SMILES for NP0249599 ((-)-β-thujone)
CC(C)[C@]12C[C@H]1[C@@H](C)C(=O)C2
Download
INCHI for NP0249599 ((-)-β-thujone)
InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8+,10-/m1/s1
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View in JSmol
Synonyms
ValueSource
(1R,4R,5S)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-oneChEBI
(-)-beta-ThujoneHMDB
(-)-cis-ThujoneHMDB
(-)-IsothujoneHMDB
L-IsothujoneHMDB
(-)-b-ThujoneGenerator
(-)-Β-thujoneGenerator
Chemical FormulaC10H16O
Average Mass152.2334 Da
Monoisotopic Mass152.12012 Da
IUPAC Name(1R,4R,5S)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one
Traditional Name(-)-β-thujone
CAS Registry NumberNot Available
SMILES
CC(C)[C@]12C[C@H]1[C@@H](C)C(=O)C2
InChI Identifier
InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3/t7-,8+,10-/m1/s1
InChI KeyUSMNOWBWPHYOEA-KHQFGBGNSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artemisia gmeliniiLOTUS Database
Artemisia herba-albaLOTUS Database
Teucrium poliumLOTUS Database
Thymus marschallianusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentBicyclic monoterpenoids  
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
    • 

  • Thujane monoterpenoid
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic 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
logP1.74ALOGPS
logP2.28ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.54 m³·mol⁻¹ChemAxon
Polarizability18.02 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036114  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014961  
KNApSAcK IDNot Available
Chemspider ID5026861  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6553876  
PDB IDNot Available
ChEBI ID50046  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]