2D

3D

Save

Zoom
- 0 of 2 defined stereocentres

Methyl 4-{[3,5-bis(trifluoromethyl)phenyl]amino}-3-chloro-2-hydroxy-4-oxo-2-(trifluoromethyl)butanoate

ChemSpider ID: 3645508
Molecular Formula: C₁₄H₉ClF₉NO₄
Average mass: 461.664215 Da
Monoisotopic mass: 461.007629 Da
Systematic name

Methyl 4-{[3,5-bis(trifluoromethyl)phenyl]amino}-3-chloro-2-hydroxy-4-oxo-2-(trifluoromethyl)butanoate
SMILES and InChIs

SMILES:

O=C(Nc1cc(cc(c1)C(F)(F)F)C(F)(F)F)C(Cl)C(O)(C(=O)OC)C(F)(F)F Copied

Std. InChI:

InChI=1S/C14H9ClF9NO4/c1-29-10(27)11(28,14(22,23)24)8(15)9(26)25-7-3-5(12(16,17)18)2-6(4-7)13(19,20)21/h2-4,8,28H,1H3,(H,25,26) Copied

Std. InChIKey:

NGHHGEJAMKZNMY-UHFFFAOYSA-N Copied
Cite this record
CSID:3645508, http://www.chemspider.com/Chemical-Structure.3645508.html (accessed 14:13, May 26, 2012) Copied

Names and Identifiers

ChemSpider Searches

Data supplied by datasources and users.

experimental physchem properties
- logP:
  
  7.827 Vitas-M

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

ACD/LogP:	7.827	# of Rule of 5 Violations:	1
ACD/LogD (pH 5.5):	7.83	ACD/LogD (pH 7.4):	7.80
ACD/BCF (pH 5.5):	522917.80	ACD/BCF (pH 7.4):	485887.10
ACD/KOC (pH 5.5):	431227.10	ACD/KOC (pH 7.4):	400689.50
#H bond acceptors:	5	#H bond donors:	2
#Freely Rotating Bonds:	6	Polar Surface Area:	75.63 Å²
Index of Refraction:	1.457	Molar Refractivity:	77.556 cm³
Molar Volume:	284.753 cm³	Polarizability:	30.746 10^-24cm³
Surface Tension:	32.6290016174316 dyne/cm	Density:	1.621 g/cm³
Flash Point:	228.931 °C	Enthalpy of Vaporization:	75.3 kJ/mol
Boiling Point:	454.926 °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) =  2.90

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  417.60  (Adapted Stein & Brown method)
    Melting Pt (deg C):  174.11  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.6E-009  (Modified Grain method)
    Subcooled liquid VP: 5.61E-008 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):  4.236
       log Kow used: 2.90 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.2318 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Esters
       Haloacetamides
       Benzyl Halides

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.46E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.294E-010 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  2.90  (KowWin est)
  Log Kaw used:  -7.461  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.361
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :  -0.9445
   Biowin2 (Non-Linear Model)     :   0.0000
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   0.3408  (recalcitrant)
   Biowin4 (Primary Survey Model) :   2.5388  (weeks-months)
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.0085
   Biowin6 (MITI Non-Linear Model):   0.0000
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.4405
 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):  7.48E-006 Pa (5.61E-008 mm Hg)
  Log Koa (Koawin est  ): 10.361
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.401 
       Octanol/air (Koa) model:  0.00564 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.935 
       Mackay model           :  0.97 
       Octanol/air (Koa) model:  0.311 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =   2.7430 E-12 cm3/molecule-sec
      Half-Life =     3.899 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    46.793 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.953 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  1097
      Log Koc:  3.040 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  1.377E-006  L/mol-sec
  Kb Half-Life at pH 8: 1.595E+004  years  
  Kb Half-Life at pH 7: 1.595E+005  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 1.529 (BCF = 33.82)
       log Kow used: 2.90 (estimated)

 Volatilization from Water:
    Henry LC:  8.46E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.487E+006  hours   (6.196E+004 days)
    Half-Life from Model Lake : 1.622E+007  hours   (6.759E+005 days)

 Removal In Wastewater Treatment:
    Total removal:               4.92  percent
    Total biodegradation:        0.12  percent
    Total sludge adsorption:     4.81  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       0.0294          93.6         1000       
   Water     7.74            4.32e+003    1000       
   Soil      92.1            8.64e+003    1000       
   Sediment  0.17            3.89e+004    0          
     Persistence Time: 5.92e+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	ER, estrogen receptor; agonist	1l2i	0.44
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.05
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.05
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.05
Serine Proteases	FXa, factor Xa	1f0r	0.05
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.05
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.04
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.02
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.02
Kinases	HSP90, human heat shock protein 90	1uy6	0.02
Kinases	EGFr, epidermal growth factor receptor	1m17	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Other Enzymes	InhA, enoyl ACP reductase	1p44	0.01
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.01
Other Enzymes	COX-1, cyclooxygenase-1	1p4g	0.01
Nuclear Hormone Receptors	ER, estrogen receptor; antagonist	3ert	0.01
Metalloenzymes	PDE5, phosphodiesterase 5	1xp0	0.01
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.00
Nuclear Hormone Receptors	GR, glucocorticoid receptor	1m2z	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Serine Proteases	Thrombin	1ba8	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00
Kinases	TK, thymidine kinase	1kim	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Other Enzymes	HIVPR, HIV protease	1hpx	0.00
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Serine Proteases	Trypsin	1bju	0.00

Want to comment
on this record?

Methyl 4-{[3,5-bis(trifluoromethyl)phenyl]amino}-3-chloro-2-hydroxy-4-oxo-2-(trifluoromethyl)butanoate

SMILES:

Std. InChI:

Std. InChIKey:

Names and Identifiers

ChemSpider Searches

Search ChemSpider for:

Search external sites for this structure:

Properties

Spectra

CIFs

Chemical Vendors

Data Sources

Patents

Pharmacological Links

SimBioSys LASSO

Want to commenton this record?

Methyl 4-{[3,5-bis(trifluoromethyl)phenyl]amino}-3-chloro-2-hydroxy-4-oxo-2-(trifluoromethyl)butanoate

SMILES:

Std. InChI:

Std. InChIKey:

Search ChemSpider for:

Search external sites for this structure:

Want to comment
on this record?