InChI=1/C19H21NO3/c1-20-9-8-19-12-5-7-15(22-3)18(19)23-17-14(21-2)6-4-11(16(17)19)10-13(12)20/h4-7,13,18H,8-10H2,1-3H3/t13-,18+,19+/m1/s1

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Search term: FQXXSQDCDRQNQE-VMDGZTHMBG
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Inherent Properties, Identifiers and References

ChemSpider ID:	4481822
Empirical Formula:	C₁₉H₂₁NO₃
Molecular Weight:	311.3749
Nominal Mass:	311 Da
Average Mass:	311.3749 Da
Monoisotopic Mass:	311.152144 Da

Systematic Name:

SMILES:

O(c5ccc4c2c5O[C@H]3C(/OC)=C\C=C1\[C@H](N(CC[C@]123)C)C4)C

InChI:

InChI=1/C19H21NO3/c1-20-9-8-19-12-5-7-15(22-3)18(19)23-17-14(21-2)6-4-11(16(17)19)10-13(12)20/h4-7,13,18H,8-10H2,1-3H3/t13-,18+,19+/m1/s1

InChIKey:

FQXXSQDCDRQNQE-VMDGZTHMBG

Std. InChI:

InChI=1S/C19H21NO3/c1-20-9-8-19-12-5-7-15(22-3)18(19)23-17-14(21-2)6-4-11(16(17)19)10-13(12)20/h4-7,13,18H,8-10H2,1-3H3/t13-,18+,19+/m1/s1

Std. InChIKey:

FQXXSQDCDRQNQE-VMDGZTHMSA-N

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Wikipedia Article(s)

Thebaine (paramorphine) is an opiate alkaloid. A minor constituent of opium, thebaine is chemically similar to both morphine and codeine, but has stimulatory rather than depressant effects, causing strychnine-like convulsions at higher doses. Thebaine is not used therapeutically, but can be converted industrially into a variety of compounds including oxycodone, oxymorphone, nalbuphine, naloxone, naltrexone, buprenorphine and etorphine. It is controlled under international law, is listed as a Class A drug under the Misuse of Drugs Act 1971 in the United Kingdom and is controlled as a Schedule II of the Controlled Substances Act in the United States of America. Read more... or Edit at Wikipedia...

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Names and Synonyms

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

(5alpha)-3,6-Dimethoxy-17-methyl-6,7,8,14-tetradehydro-4,5-epoxymorphinan

115-37-7 [RN]

204-084-1 [EINECS/ELINCS]

Morphinan, 6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methyl-, (5.alpha.)-

morphinan, 6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methyl-, (5alpha)-

(5alpha)-6,7,8,14-tetradehydro-4,5-epoxy-3,6-dimethoxy-17-methylmorphinan

(5R,9R,13S)-4,5-epoxy-3,6-dimethoxy-9alpha-methyl-6,8-morphinadien

3,6-dimethoxy-17-methyl-6,7,8,14-tetradehydro-4,5alpha-epoxymorphinan

3,6-dimethoxy-17-methyl-6,7,8,14-tetradehydro-4,5-epoxymorphinan

3-O-methyl-oripavin

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Database ID(s)

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

ACD/Labs Predicted Properties

ACD/LogP:	2.40	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	0.47	ACD/LogD (pH 7.4):	2.07
ACD/BCF (pH 5.5):	1	ACD/BCF (pH 7.4):	18.35
ACD/KOC (pH 5.5):	5.59	ACD/KOC (pH 7.4):	224.53
#H bond acceptors:	4	#H bond donors:	0
#Freely Rotating Bonds:	2	Polar Surface Area:	30.93 Å²
Index of Refraction:	1.648	Molar Refractivity:	87.19 cm³
Molar Volume:	239.3 cm³	Polarizability:	34.56 10^-24cm³
Surface Tension:	53.8 dyne/cm	Density:	1.3 g/cm³
Flash Point:	141 °C	Enthalpy of Vaporization:	72.97 kJ/mol
Boiling Point:	467.6 °C at 760 mmHg	Vapour Pressure:	6.4E-09 mmHg at 25°C

MeSH

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  2.02

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  395.93  (Adapted Stein & Brown method)
    Melting Pt (deg C):  163.99  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.8E-007  (Modified Grain method)
    MP  (exp database):  193 deg C
    Subcooled liquid VP: 1.04E-005 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):  2019
       log Kow used: 2.02 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  680 mg/L (15 deg C)
        Exper. Ref:  MERCK INDEX (1996)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  31.384 mg/L
    Wat Sol (Exper. database match) =  680.00
       Exper. Ref:  MERCK INDEX (1996)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Vinyl/Allyl Ethers

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.63E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  3.653E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.02  (KowWin est)
  Log Kaw used:  -8.176  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.196
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1812
   Biowin2 (Non-Linear Model)     :   0.0238
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.8444  (months      )
   Biowin4 (Primary Survey Model) :   3.0330  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.1992
   Biowin6 (MITI Non-Linear Model):   0.0194
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.3338
 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):  0.00139 Pa (1.04E-005 mm Hg)
  Log Koa (Koawin est  ): 10.196
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00216 
       Octanol/air (Koa) model:  0.00385 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0725 
       Mackay model           :  0.148 
       Octanol/air (Koa) model:  0.236 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 507.1271 E-12 cm3/molecule-sec
      Half-Life =     0.021 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    15.186 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =   171.112503 E-17 cm3/molecule-sec
      Half-Life =     0.007 Days (at 7E11 mol/cm3)
      Half-Life =      9.644 Min
   Fraction sorbed to airborne particulates (phi): 0.11 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  4535
      Log Koc:  3.657 

 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 = 0.856 (BCF = 7.172)
       log Kow used: 2.02 (estimated)

 Volatilization from Water:
    Henry LC:  1.63E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.338E+006  hours   (2.641E+005 days)
    Half-Life from Model Lake : 6.915E+007  hours   (2.881E+006 days)

 Removal In Wastewater Treatment:
    Total removal:               2.26  percent
    Total biodegradation:        0.10  percent
    Total sludge adsorption:     2.17  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       0.00111         0.122        1000       
   Water     24.1            1.44e+003    1000       
   Soil      75.8            2.88e+003    1000       
   Sediment  0.0976          1.3e+004     0          
     Persistence Time: 1.66e+003 hr

SimBioSys LASSO

Descriptors: 0, 0, 0, 0, 0, 0, 0, 7, 0, 0, 0, 0, 4, 4, 13, 0, 8, 0, 0, 0, 2, 0, 0, 0

Category	Target	PDB Code	LASSO Score
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.02
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.02
Kinases	SRC, tyrosine kinase SRC	2src	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
Serine Proteases	Thrombin	1ba8	0.01
Kinases	HSP90, human heat shock protein 90	1uy6	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Other Enzymes	InhA, enoyl ACP reductase	1p44	0.01
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.01
Nuclear Hormone Receptors	GR, glucocorticoid receptor	1m2z	0.00
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
Kinases	TK, thymidine kinase	1kim	0.00
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; antagonist	3ert	0.00
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Other Enzymes	COX-1, cyclooxygenase-1	1p4g	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Serine Proteases	Trypsin	1bju	0.00