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- 4 of 4 defined stereocentres

Methyl (2S,3aR,7S,7aS)-6-oxo-1-[(2E)-3-phenyl-2-propen-1-yl]-7-(2-propyn-1-yl)-2,3,3a,6,7,7a-hexahydro-1H-indole-2-carboxylate

ChemSpider ID: 4575179
Molecular Formula: C₂₂H₂₃NO₃
Average mass: 349.422913 Da
Monoisotopic mass: 349.167786 Da
Systematic name

Methyl (2S,3aR,7S,7aS)-6-oxo-1-[(2E)-3-phenyl-2-propen-1-yl]-7-(2-propyn-1-yl)-2,3,3a,6,7,7a-hexahydro-1H-indole-2-carboxylate
SMILES and InChIs

SMILES:

O=C1\C=C/[C@H]2C[C@@H](C(=O)OC)N([C@@H]2[C@@H]1CC#C)C\C=C\c3ccccc3 Copied

Std. InChI:

InChI=1S/C22H23NO3/c1-3-8-18-20(24)13-12-17-15-19(22(25)26-2)23(21(17)18)14-7-11-16-9-5-4-6-10-16/h1,4-7,9-13,17-19,21H,8,14-15H2,2H3/b11-7+/t17-,18+,19-,21-/m0/s1 Copied

Std. InChIKey:

JBWFADGTVJXTOW-DQKVDQNHSA-N Copied
Cite this record
CSID:4575179, http://www.chemspider.com/Chemical-Structure.4575179.html (accessed 09:46, Jun 19, 2013) Copied

Names and Identifiers

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

ACD/LogP:	2.664	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	2.29	ACD/LogD (pH 7.4):	2.66
ACD/BCF (pH 5.5):	26.34	ACD/BCF (pH 7.4):	61.22
ACD/KOC (pH 5.5):	283.30	ACD/KOC (pH 7.4):	658.55
#H bond acceptors:	4	#H bond donors:	0
#Freely Rotating Bonds:	6	Polar Surface Area:	46.61 Å²
Index of Refraction:	1.581	Molar Refractivity:	101.139 cm³
Molar Volume:	303.43 cm³	Polarizability:	40.095 10^-24cm³
Surface Tension:	45.7779998779297 dyne/cm	Density:	1.152 g/cm³
Flash Point:	261.105 °C	Enthalpy of Vaporization:	77.838 kJ/mol
Boiling Point:	508.126 °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) =  2.87

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  454.21  (Adapted Stein & Brown method)
    Melting Pt (deg C):  187.87  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  7.64E-009  (Modified Grain method)
    Subcooled liquid VP: 3.86E-007 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):  227.2
       log Kow used: 2.87 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  2.2868 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.63E-012  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.546E-011 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.87  (KowWin est)
  Log Kaw used:  -9.638  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.508
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6850
   Biowin2 (Non-Linear Model)     :   0.7772
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3119  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.2672  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2838
   Biowin6 (MITI Non-Linear Model):   0.0217
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.0017
 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):  5.15E-005 Pa (3.86E-007 mm Hg)
  Log Koa (Koawin est  ): 12.508
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0583 
       Octanol/air (Koa) model:  0.791 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.678 
       Mackay model           :  0.823 
       Octanol/air (Koa) model:  0.984 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 259.3168 E-12 cm3/molecule-sec [Cis-isomer]
      OVERALL OH Rate Constant = 266.9168 E-12 cm3/molecule-sec [Trans-isomer]
      Half-Life =   29.698 Min (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
      Half-Life =   28.852 Min (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     7.965499 E-17 cm3/molecule-sec [Cis-]
      OVERALL Ozone Rate Constant =    14.790500 E-17 cm3/molecule-sec [Trans-]
      Half-Life =   207.173 Min (at 7E11 mol/cm3) [Cis-isomer]
      Half-Life =   111.574 Min (at 7E11 mol/cm3) [Trans-isomer]
   Fraction sorbed to airborne particulates (phi): 0.751 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  2.637E+004
      Log Koc:  4.421 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  1.849E-003  L/mol-sec
  Kb Half-Life at pH 8:      11.877  years  
  Kb Half-Life at pH 7:     118.766  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.506 (BCF = 32.09)
       log Kow used: 2.87 (estimated)

 Volatilization from Water:
    Henry LC:  5.63E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.944E+008  hours   (8.1E+006 days)
    Half-Life from Model Lake : 2.121E+009  hours   (8.836E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               4.73  percent
    Total biodegradation:        0.12  percent
    Total sludge adsorption:     4.61  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       0.000169        0.769        1000       
   Water     13.4            900          1000       
   Soil      86.3            1.8e+003     1000       
   Sediment  0.23            8.1e+003     0          
     Persistence Time: 1.75e+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	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
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
Serine Proteases	Thrombin	1ba8	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
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.00
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	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
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Other Enzymes	InhA, enoyl ACP reductase	1p44	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Serine Proteases	Trypsin	1bju	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Nuclear Hormone Receptors	GR, glucocorticoid receptor	1m2z	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
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	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	TK, thymidine kinase	1kim	0.00

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Methyl (2S,3aR,7S,7aS)-6-oxo-1-[(2E)-3-phenyl-2-propen-1-yl]-7-(2-propyn-1-yl)-2,3,3a,6,7,7a-hexahydro-1H-indole-2-carboxylate

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Methyl (2S,3aR,7S,7aS)-6-oxo-1-[(2E)-3-phenyl-2-propen-1-yl]-7-(2-propyn-1-yl)-2,3,3a,6,7,7a-hexahydro-1H-indole-2-carboxylate

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