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THC

ChemSpider ID: 2872
Molecular Formula: C₂₁H₃₀O₂
Average mass: 314.4617 Da
Monoisotopic mass: 314.224579 Da
Systematic name

6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol
SMILES and InChIs

SMILES:

Oc2cc(cc1OC(C3CC/C(=C\C3c12)C)(C)C)CCCCC Copied

Std. InChI:

InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3 Copied

Std. InChIKey:

CYQFCXCEBYINGO-UHFFFAOYSA-N Copied
Cite this record
CSID:2872, http://www.chemspider.com/Chemical-Structure.2872.html (accessed 20:27, Jun 19, 2013) Copied

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

3-Pentyl-6,6,9-trimethyl-6a,7,8,10a-tetrahydro-6H-dibenzo(b,d)pyran-1-ol

6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol [ACD/IUPAC Name]

6a,7,8,10a-Tetrahydro-3-pentyl-6,6,9-trimethyl-6H-dibenzo(b,d)pyran-1-ol

6H-Dibenzo(b,d)pyran-1-ol, 6a,7,8,10a-tetrahydro-3-pentyl-6,6,9-trimethyl-

6H-dibenzo[b,d]pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-

THC

1972-08-3 [RN]

6,6,9-Trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol (δ9-THC)

6H-Dibenzo(b,d)pyran-1-ol, 6a,7,8,10a-tetrahydro-6,6,9-trimethyl-3-pentyl-, (6aR-trans)-

76-03-9 [RN]

More...

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

DEA No. 7369 [DBID]

DEA No. 7370 [DBID]

DivK1c_000977 [DBID]

KBio1_000977 [DBID]

NINDS_000977 [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:	6.838	# of Rule of 5 Violations:	1
ACD/LogD (pH 5.5):	6.84	ACD/LogD (pH 7.4):	6.84
ACD/BCF (pH 5.5):	92683.19	ACD/BCF (pH 7.4):	92330.54
ACD/KOC (pH 5.5):	125012.20	ACD/KOC (pH 7.4):	124536.60
#H bond acceptors:	2	#H bond donors:	1
#Freely Rotating Bonds:	5	Polar Surface Area:	29.46 Å²
Index of Refraction:	1.529	Molar Refractivity:	95.49 cm³
Molar Volume:	309.738 cm³	Polarizability:	37.855 10^-24cm³
Surface Tension:	35.0670013427734 dyne/cm	Density:	1.015 g/cm³
Flash Point:	149.334 °C	Enthalpy of Vaporization:	66.493 kJ/mol
Boiling Point:	390.448 °C at 760 mmHg	Vapour Pressure:	0 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) =  7.60
    Log Kow (Exper. database match) =  6.97
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  407.23  (Adapted Stein & Brown method)
    Melting Pt (deg C):  160.26  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  4.63E-008  (Modified Grain method)
    BP  (exp database):  200 @ 0.02 mm Hg deg C
    Subcooled liquid VP: 1.13E-006 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  0.04284
       log Kow used: 6.97 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  2800 mg/L (23 deg C)
        Exper. Ref:  NIH NTP Reports web-site

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  0.02054 mg/L
    Wat Sol (Exper. database match) =  2800.00
       Exper. Ref:  NIH NTP Reports web-site

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.44E-007  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  4.472E-007 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  6.97  (exp database)
  Log Kaw used:  -5.001  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  11.971
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.8794
   Biowin2 (Non-Linear Model)     :   0.9514
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.4390  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.4894  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2626
   Biowin6 (MITI Non-Linear Model):   0.0974
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4656
 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):  0.000151 Pa (1.13E-006 mm Hg)
  Log Koa (Koawin est  ): 11.971
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0199 
       Octanol/air (Koa) model:  0.23 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.418 
       Mackay model           :  0.614 
       Octanol/air (Koa) model:  0.948 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 308.6397 E-12 cm3/molecule-sec
      Half-Life =     0.035 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    24.952 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    43.000000 E-17 cm3/molecule-sec
      Half-Life =     0.027 Days (at 7E11 mol/cm3)
      Half-Life =     38.378 Min
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.516 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  6.118E+005
      Log Koc:  5.787 

 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 = 4.667 (BCF = 4.644e+004)
       log Kow used: 6.97 (expkow database)

 Volatilization from Water:
    Henry LC:  2.44E-007 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River:       4257  hours   (177.4 days)
    Half-Life from Model Lake : 4.659E+004  hours   (1941 days)

 Removal In Wastewater Treatment:
    Total removal:              93.83  percent
    Total biodegradation:        0.78  percent
    Total sludge adsorption:    93.05  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.00569         0.362        1000       
   Water     2.17            900          1000       
   Soil      29              1.8e+003     1000       
   Sediment  68.8            8.1e+003     0          
     Persistence Time: 3.01e+003 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	AR, androgen receptor	1xq2	0.42
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
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.02
Kinases	TK, thymidine kinase	1kim	0.01
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.01
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Serine Proteases	Thrombin	1ba8	0.01
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Other Enzymes	HIVPR, HIV protease	1hpx	0.01
Metalloenzymes	PDE5, phosphodiesterase 5	1xp0	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	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
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	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
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	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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THC

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THC