NP-MRD: Showing NP-Card for Isothujone (NP0006808)

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Record Information

Version

2.0

Created at

2020-12-09 03:44:13 UTC

Updated at

2021-08-19 23:59:43 UTC

NP-MRD ID

NP0006808

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isothujone

Provided By

NPAtlas

Description

(+)-3-Thujone, also known as beta-thujone or β-thujone, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, (+)-3-thujone is considered to be an isoprenoid. Isothujone is found in Achillea abrotanoides, Achillea fragrantissima, Achillea grandifolia, Achillea millefolium, Achillea moschata, Aloysia citrodora, Artemisia absinthium , Artemisia afra, Artemisia annua, Artemisia arborescens, Artemisia baldshuanica, Artemisia halophila, Artemisia herba-alba , Artemisia sericea, Artemisia thuscula, Artemisia tridentata, Catha edulis, Chrysanthemum boreale, Chrysanthemum vulgare, Cleonia lusitanica, Cotula cinerea, Chenopodium ambrosioides , Ganoderma lucidum , Helichrysum italicum, Juniperus communis, Juniperus foetidissima, Juniperus sabina , Micromeria biflora, Origanum majorana, Pimenta racemosa, Thuja orientalis , Polygala senega, Rhodiola rosea, Rhododendron mucronulatum, Salvia absconditiflora, Salvia fruticosa, Salvia pisidica, Salvia pomifera, Salvia sclarea, Salvia tomentosa, Sideritis tragoriganum, Streptomyces, Tetradenia riparia , Thuja occidentalis , Thuja standishii, Thujopsis dolabrata, Thymus cilicicus, Thymus fedtschenkoi, Thymus zygioides, Vitex agnus-castus and Xylopia aromatica. Isothujone was first documented in 1976 (PMID: 966252). Based on a literature review a significant number of articles have been published on (+)-3-Thujone (PMID: 23081929) (PMID: 22493561) (PMID: 23413575) (PMID: 9614092) (PMID: 23439844) (PMID: 12670167).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118353D          

 27 28  0  0  0  0            999 V2000
   -2.6095   -0.2226   -0.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6011   -0.5531    0.1564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1591   -0.0230    1.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2590    0.0791   -0.1648 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4175   -0.3103   -1.4367 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5808   -1.1280   -0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0592   -2.1252   -1.4591 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0295   -0.4326    0.2992 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0596    0.6091    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7796    0.1062    0.9214 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1442    1.3503    0.4703 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5627    0.8410   -1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4968   -0.9106   -1.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6233   -0.4344   -0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4450   -1.6484    0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4812   -0.1401    2.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5119    1.0132    1.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0590   -0.6622    1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366   -0.9291   -2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8138    0.5786   -1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4713   -1.2218    0.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9723    0.4343    0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3570    0.4974   -1.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7169    1.6422    0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -0.3179    1.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6001    1.7951    1.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7269    2.1127   -0.0856 H   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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10  4  1  0  0  0  0
 11  4  1  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  2 15  1  1  0  0  0
  3 16  1  0  0  0  0
  3 17  1  0  0  0  0
  3 18  1  0  0  0  0
  5 19  1  0  0  0  0
  5 20  1  0  0  0  0
  8 21  1  1  0  0  0
  9 22  1  0  0  0  0
  9 23  1  0  0  0  0
  9 24  1  0  0  0  0
 10 25  1  1  0  0  0
 11 26  1  0  0  0  0
 11 27  1  0  0  0  0
M  END


  Mrv1652306242118353D          

 27 28  0  0  0  0            999 V2000
   -2.6095   -0.2226   -0.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6011   -0.5531    0.1564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1591   -0.0230    1.4580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2590    0.0791   -0.1648 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4175   -0.3103   -1.4367 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5808   -1.1280   -0.9565 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0592   -2.1252   -1.4591 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0295   -0.4326    0.2992 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0596    0.6091    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7796    0.1062    0.9214 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1442    1.3503    0.4703 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5627    0.8410   -1.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4968   -0.9106   -1.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6233   -0.4344   -0.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4450   -1.6484    0.1897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4812   -0.1401    2.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5119    1.0132    1.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0590   -0.6622    1.6878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366   -0.9291   -2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8138    0.5786   -1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4713   -1.2218    0.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9723    0.4343    0.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3570    0.4974   -1.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7169    1.6422    0.1443 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167   -0.3179    1.9299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6001    1.7951    1.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7269    2.1127   -0.0856 H   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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10  4  1  0  0  0  0
 11  4  1  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  2 15  1  1  0  0  0
  3 16  1  0  0  0  0
  3 17  1  0  0  0  0
  3 18  1  0  0  0  0
  5 19  1  0  0  0  0
  5 20  1  0  0  0  0
  8 21  1  1  0  0  0
  9 22  1  0  0  0  0
  9 23  1  0  0  0  0
  9 24  1  0  0  0  0
 10 25  1  1  0  0  0
 11 26  1  0  0  0  0
 11 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006808

> <DATABASE_NAME>
NP-MRD

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

> <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-/m0/s1

> <INCHI_KEY>
USMNOWBWPHYOEA-XKSSXDPKSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.2334

> <EXACT_MASS>
152.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.012467468026905

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S,5R)-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

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.610  -0.223  -0.924  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.601  -0.553   0.156  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.159  -0.023   1.458  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.259   0.079  -0.165  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.418  -0.310  -1.437  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.581  -1.128  -0.957  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.059  -2.125  -1.459  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.030  -0.433   0.299  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.060   0.609   0.005  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.780   0.106   0.921  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.144   1.350   0.470  0.00  0.00           C+0
HETATM   12  H   UNK     0      -2.563   0.841  -1.202  0.00  0.00           H+0
HETATM   13  H   UNK     0      -2.497  -0.911  -1.791  0.00  0.00           H+0
HETATM   14  H   UNK     0      -3.623  -0.434  -0.475  0.00  0.00           H+0
HETATM   15  H   UNK     0      -1.445  -1.648   0.190  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.481  -0.140   2.304  0.00  0.00           H+0
HETATM   17  H   UNK     0      -2.512   1.013   1.290  0.00  0.00           H+0
HETATM   18  H   UNK     0      -3.059  -0.662   1.688  0.00  0.00           H+0
HETATM   19  H   UNK     0      -0.237  -0.929  -2.066  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.814   0.579  -1.980  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.471  -1.222   0.937  0.00  0.00           H+0
HETATM   22  H   UNK     0       3.972   0.434   0.641  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.357   0.497  -1.071  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.717   1.642   0.144  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.517  -0.318   1.930  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.600   1.795   1.180  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.727   2.113  -0.086  0.00  0.00           H+0
CONECT    1    2   12   13   14                                             
CONECT    2    1    3    4   15                                             
CONECT    3    2   16   17   18                                             
CONECT    4    2    5   10   11                                             
CONECT    5    4    6   19   20                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   21                                             
CONECT    9    8   22   23   24                                             
CONECT   10    8   11    4   25                                             
CONECT   11   10    4   26   27                                             
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15    2                                                            
CONECT   16    3                                                            
CONECT   17    3                                                            
CONECT   18    3                                                            
CONECT   19    5                                                            
CONECT   20    5                                                            
CONECT   21    8                                                            
CONECT   22    9                                                            
CONECT   23    9                                                            
CONECT   24    9                                                            
CONECT   25   10                                                            
CONECT   26   11                                                            
CONECT   27   11                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(+)-Isothujone	ChEBI
(1S,4S,5R)-(+)-3-Thujanone	ChEBI
(1S,4S,5R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one	ChEBI
[1S-(1alpha,4beta,5alpha)]-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one	ChEBI
beta-Thujone	ChEBI
D-beta-Thujone	ChEBI
D-Isothujone	ChEBI
trans-Thujone	ChEBI
[1S-(1a,4b,5a)]-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one	Generator
[1S-(1Α,4β,5α)]-4-methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one	Generator
b-Thujone	Generator
Β-thujone	Generator
D-b-Thujone	Generator
D-Β-thujone	Generator
(+)-b-Thujone	HMDB
(+)-beta-Thujone	HMDB
(+)-cis-Thujone	HMDB
(+)-Thujone	HMDB
-Thujone	HMDB
D-beta	HMDB
Isothujone	HMDB
(+)-Β-thujone	HMDB
alpha-Thujone	HMDB
cis-Thujone	HMDB
Thujone	HMDB
(-)-Thujone	HMDB
3-Isothujone	HMDB
3-Thujanone	HMDB
beta-Thujone, 1S-(1alpha,4beta,5alpha)-isomer	HMDB
alpha, beta-Thujone	HMDB
beta-Thujone, (1S-(1alpha,4alpha,5alpha))-isomer	HMDB
beta-Thujone, (1alpha,4alpha,5alpha)-isomer	HMDB
(+)-3-Thujone	ChEBI

Chemical Formula

C₁₀H₁₆O

Average Mass

152.2334 Da

Monoisotopic Mass

152.12012 Da

IUPAC Name

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

Traditional Name

(+)-β-thujone

CAS Registry Number

Not 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-/m0/s1

InChI Key

USMNOWBWPHYOEA-XKSSXDPKSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achillea abrotanoides	LOTUS Database	35616633
Achillea fragrantissima	LOTUS Database	35616633
Achillea grandifolia	LOTUS Database	35616633
Achillea millefolium	LOTUS Database	35616633
Achillea moschata	LOTUS Database	35616633
Aloysia citrodora	LOTUS Database	35616633
Artemisia absinthium	Plant	KNApSAcK
Artemisia afra	LOTUS Database	35616633
Artemisia annua	LOTUS Database	35616633
Artemisia arborescens	LOTUS Database	35616633
Artemisia baldshuanica	LOTUS Database	35616633
Artemisia halophila	LOTUS Database	35616633
Artemisia herba-alba	Plant	KNApSAcK
Artemisia sericea	LOTUS Database	35616633
Artemisia thuscula	LOTUS Database	35616633
Artemisia tridentata	LOTUS Database	35616633
Artemisia vulgaris	KNApSAcK Database	22123792
Catha edulis	LOTUS Database	35616633
Chenopodium ambrosioides	KNApSAcK Database	22123792
Chrysanthemum boreale	LOTUS Database	35616633
Chrysanthemum vulgare	Plant	KNApSAcK
Cistus albidus	KNApSAcK Database	22123792
Cleonia lusitanica	LOTUS Database	35616633
Cotula cinerea	LOTUS Database	35616633
Dysphania ambrosioides	Plant	KNApSAcK
Ganoderma lucidum	Fungi	KNApSAcK
Helichrysum italicum	LOTUS Database	35616633
Hyssopus officinalis L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Juniperus communis	LOTUS Database	35616633
Juniperus foetidissima	LOTUS Database	35616633
Juniperus sabina	Plant	KNApSAcK
Mentha x piperita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Micromeria biflora	LOTUS Database	35616633
Ocimum basilicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum majorana	LOTUS Database	35616633
Origanum onites	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pimenta racemosa	LOTUS Database	35616633
Pinus halepensis	KNApSAcK Database	22123792
Platycladus orientalis	Plant	KNApSAcK
Polygala senega	LOTUS Database	35616633
Rhodiola rosea	LOTUS Database	35616633
Rhodiola rosea L.	KNApSAcK Database	22123792
Rhododendron mucronulatum	LOTUS Database	35616633
Salvia absconditiflora	LOTUS Database	35616633
Salvia fruticosa	LOTUS Database	35616633
Salvia officinalis	KNApSAcK Database	22123792
Salvia pisidica	LOTUS Database	35616633
Salvia pomifera	LOTUS Database	35616633
Salvia rosmarinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Salvia sclarea	LOTUS Database	35616633
Salvia tomentosa	LOTUS Database	35616633
Satureja montana	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sideritis tragoriganum	LOTUS Database	35616633
Streptomyces	NPAtlas	17193176
Tanacetum macrophyllum	KNApSAcK Database	22123792
Tanacetum vulgare	KNApSAcK Database	22123792
Tetradenia riparia	Plant	KNApSAcK
Thuja occidentalis	Plant	KNApSAcK
Thuja plicata	KNApSAcK Database	22123792
Thuja standishii	LOTUS Database	35616633
Thujopsis dolabrata	LOTUS Database	35616633
Thymus cilicicus	LOTUS Database	35616633
Thymus fedtschenkoi	LOTUS Database	35616633
Thymus zygioides	LOTUS Database	35616633
Vitex agnus-castus	LOTUS Database	35616633
Xylopia aromatica	LOTUS Database	35616633
Zingiber officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic 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 Framework

Aliphatic homopolycyclic compounds

External Descriptors

beta-thujone (CHEBI:50045 )
Bicyclic monoterpenoids (LMPR0102120039 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	407.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.74	ALOGPS
logP	2.28	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	44.54 m³·mol⁻¹	ChemAxon
Polarizability	18.01 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA014293

HMDB ID

HMDB0036113

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91456

PDB ID

Not Available

ChEBI ID

50045

Good Scents ID

rw1384741

References

General References

Jug-Dujakovic M, Ristic M, Pljevljakusic D, Dajic-Stevanovic Z, Liber Z, Hancevic K, Radic T, Satovic Z: High diversity of indigenous populations of dalmatian sage (Salvia officinalis L.) in essential-oil composition. Chem Biodivers. 2012 Oct;9(10):2309-23. doi: 10.1002/cbdv.201200131. [PubMed:23081929 ]
Walch SG, Lachenmeier DW, Kuballa T, Stuhlinger W, Monakhova YB: Holistic Control of Herbal Teas and Tinctures Based on Sage (Salvia officinalis L.) for Compounds with Beneficial and Adverse Effects using NMR Spectroscopy. Anal Chem Insights. 2012;7:1-12. doi: 10.4137/ACI.S8946. Epub 2012 Mar 21. [PubMed:22493561 ]
Satyal P, Paudel P, Kafle A, Pokharel SK, Lamichhane B, Dosoky NS, Moriarity DM, Setzer WN: Bioactivities of volatile components from Nepalese Artemisia species. Nat Prod Commun. 2012 Dec;7(12):1651-8. [PubMed:23413575 ]
Rice KC, Wilson RS: (-)-3-Isothujone, a small nonnitrogenous molecule with antinociceptive activity in mice. J Med Chem. 1976 Aug;19(8):1054-7. doi: 10.1021/jm00230a015. [PubMed:966252 ]
Wise ML, Savage TJ, Katahira E, Croteau R: Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase. J Biol Chem. 1998 Jun 12;273(24):14891-9. doi: 10.1074/jbc.273.24.14891. [PubMed:9614092 ]
Haider SZ, Andola HC, Mohan M: Constituents of Artemisia gmelinii Weber ex Stechm. from Uttarakhand Himalaya: A Source of Artemisia Ketone. Indian J Pharm Sci. 2012 May;74(3):265-7. doi: 10.4103/0250-474X.106074. [PubMed:23439844 ]
Santos-Gomes PC, Fernandes-Ferreira M: Essential oils produced by in vitro shoots of sage (Salvia officinalis L.). J Agric Food Chem. 2003 Apr 9;51(8):2260-6. doi: 10.1021/jf020945v. [PubMed:12670167 ]
Dehal SS, Croteau R: Metabolism of monoterpenes: specificity of the dehydrogenases responsible for the biosynthesis of camphor, 3-thujone, and 3-isothujone. Arch Biochem Biophys. 1987 Oct;258(1):287-91. doi: 10.1016/0003-9861(87)90346-8. [PubMed:3310901 ]
Kolassa N: Menthol differs from other terpenic essential oil constituents. Regul Toxicol Pharmacol. 2013 Feb;65(1):115-8. doi: 10.1016/j.yrtph.2012.11.009. Epub 2012 Dec 1. [PubMed:23207345 ]
Tayade AB, Dhar P, Kumar J, Sharma M, Chauhan RS, Chaurasia OP, Srivastava RB: Chemometric profile of root extracts of Rhodiola imbricata Edgew. with hyphenated gas chromatography mass spectrometric technique. PLoS One. 2013;8(1):e52797. doi: 10.1371/journal.pone.0052797. Epub 2013 Jan 10. [PubMed:23326358 ]
Raut JS, Shinde RB, Chauhan NM, Karuppayil SM: Terpenoids of plant origin inhibit morphogenesis, adhesion, and biofilm formation by Candida albicans. Biofouling. 2013;29(1):87-96. doi: 10.1080/08927014.2012.749398. [PubMed:23216018 ]

Showing NP-Card for Isothujone (NP0006808)

MOL for NP0006808 (Isothujone)

3D MOL for NP0006808 (Isothujone)

3D SDF for NP0006808 (Isothujone)

3D-SDF for NP0006808 (Isothujone)

PDB for NP0006808 (Isothujone)

3D PDB for NP0006808 (Isothujone)

SMILES for NP0006808 (Isothujone)

INCHI for NP0006808 (Isothujone)

Structure for NP0006808 (Isothujone)

3D Structure for NP0006808 (Isothujone)