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α-Thujone

ChemSpider ID: 229574
Molecular Formula: C₁₀H₁₆O
Average mass: 152.233398 Da
Monoisotopic mass: 152.120117 Da
Systematic name

(1S,4R,5R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one
SMILES and InChIs

SMILES:

O=C1[C@H](C)[C@@H]2[C@](C(C)C)(C1)C2 Copied

Std. InChI:

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 Copied

Std. InChIKey:

USMNOWBWPHYOEA-MRTMQBJTSA-N Copied
Cite this record
CSID:229574, http://www.chemspider.com/Chemical-Structure.229574.html (accessed 07:00, May 26, 2013) Copied

Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

(-)-α-Thujone

α-Thujone [Wiki]

(-)-Thujone

(-)-a-Thujone

(-)-Isothujone

(1S,4R,5R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-on

(1S,4R,5R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one

(1S,4R,5R)-1-Isopropyl-4-méthylbicyclo[3.1.0]hexan-3-one

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

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

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Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts

89231_FLUKA [DBID]

BRN 4660369 [DBID]

C09906 [DBID]

MFCD00001313 [DBID]

NCGC00091438-01 [DBID]

NSC 93742 [DBID]

NSC93742 [DBID]

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Properties

Predicted - ACD/Labs
Predicted - EPISuite
Predicted - ChemAxon

Predicted data is generated using the ACD/Labs’ ACD/PhysChem Suite, for more information see their website.

ACD/LogP:	2.044	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	2.04	ACD/LogD (pH 7.4):	2.04
ACD/BCF (pH 5.5):	21.07	ACD/BCF (pH 7.4):	21.07
ACD/KOC (pH 5.5):	308.41	ACD/KOC (pH 7.4):	308.41
#H bond acceptors:	1	#H bond donors:	0
#Freely Rotating Bonds:	1	Polar Surface Area:	17.07 Å²
Index of Refraction:	1.5	Molar Refractivity:	44.327 cm³
Molar Volume:	150.832 cm³	Polarizability:	17.573 10^-24cm³
Surface Tension:	34.9780006408691 dyne/cm	Density:	1.009 g/cm³
Flash Point:	64.444 °C	Enthalpy of Vaporization:	43.671 kJ/mol
Boiling Point:	200.499 °C at 760 mmHg	Vapour Pressure:	0.323000013828278 mmHg at 25°C

Predicted data is generated using the US Environmental Protection Agency’s EPISuite™, for more information see their website.

                    
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  2.65

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  200.58  (Adapted Stein & Brown method)
    Melting Pt (deg C):  20.76  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.449  (Mean VP of Antoine & Grain methods)
    MP  (exp database):  < 25 deg C
    BP  (exp database):  203 deg C
    VP  (exp database):  4.12E-01 mm Hg at 25 deg C

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  407.7
       log Kow used: 2.65 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  501.2 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Neutral Organics

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.00E-005  atm-m3/mole
   Group Method:   1.58E-005  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  2.206E-004 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.65  (KowWin est)
  Log Kaw used:  -2.543  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  5.193
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.4980
   Biowin2 (Non-Linear Model)     :   0.2093
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.6281  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4524  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4595
   Biowin6 (MITI Non-Linear Model):   0.3860
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4557
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  54.9 Pa (0.412 mm Hg)
  Log Koa (Koawin est  ): 5.193
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  5.46E-008 
       Octanol/air (Koa) model:  3.83E-008 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1.97E-006 
       Mackay model           :  4.37E-006 
       Octanol/air (Koa) model:  3.06E-006 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   5.1227 E-12 cm3/molecule-sec
      Half-Life =     2.088 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    25.055 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 3.17E-006 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  118.9
      Log Koc:  2.075 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.338 (BCF = 21.76)
       log Kow used: 2.65 (estimated)

 Volatilization from Water:
    Henry LC:  1.58E-005 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River:      46.98  hours   (1.958 days)
    Half-Life from Model Lake :        616  hours   (25.67 days)

 Removal In Wastewater Treatment:
    Total removal:               4.44  percent
    Total biodegradation:        0.11  percent
    Total sludge adsorption:     3.48  percent
    Total to Air:                0.86  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       1.65            50.1         1000       
   Water     21              900          1000       
   Soil      77.2            1.8e+003     1000       
   Sediment  0.228           8.1e+003     0          
     Persistence Time: 941 hr

Patents	Personal Collections
Publication or Magazine Article	Web-based Article (blog or commentary)
Available Chemicals Databases	Biological Properties
Chemical Reactions	Chemical Safety Data
Drugs or Compounds in Development	Imaging Agents
Information Aggregators	Journal Publishers via MeSH
Ligand/binding/crystal Structure Databases	Metabolic Pathways
Molecular Libraries Screening Center Network	Natural Products
NIH Substance Repository	Physical Properties (including SAR/QSAR databases)
Protein 3D Structures	Spectroscopy Databases
Substance Vendors	Theoretical Properties
Toxicology/Environmental Databases	Virtual Library

Category	Target	PDB Code	LASSO Score
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.88
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.42
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.40
Metalloenzymes	ADA, adenosine deaminase	1stw	0.24
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.14
Nuclear Hormone Receptors	GR, glucocorticoid receptor	1m2z	0.10
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.03
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.03
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
Other Enzymes	HIVPR, HIV protease	1hpx	0.01
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Serine Proteases	Thrombin	1ba8	0.01
Other Enzymes	InhA, enoyl ACP reductase	1p44	0.01
Metalloenzymes	PDE5, phosphodiesterase 5	1xp0	0.01
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.01
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.00
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00
Serine Proteases	Trypsin	1bju	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Kinases	TK, thymidine kinase	1kim	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Other Enzymes	COX-1, cyclooxygenase-1	1p4g	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; antagonist	3ert	0.00
Kinases	HSP90, human heat shock protein 90	1uy6	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00

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α-Thujone

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