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4-{[5-(1,3-Benzodioxol-5-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}-2-[(benzylamino)(hydroxy)methylene]-3-oxobutanenitrile

ChemSpider ID: 3662304
Molecular Formula: C₂₁H₁₆N₄O₅S
Average mass: 436.440491 Da
Monoisotopic mass: 436.084137 Da
Systematic name

4-{[5-(1,3-Benzodioxol-5-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}-2-[(benzylamino)(hydroxy)methylene]-3-oxobutanenitrile
SMILES and InChIs

SMILES:

N#CC(=C(O)NCc1ccccc1)C(=O)CSc2nnc(o2)c3ccc4OCOc4c3 Copied

Std. InChI:

InChI=1S/C21H16N4O5S/c22-9-15(19(27)23-10-13-4-2-1-3-5-13)16(26)11-31-21-25-24-20(30-21)14-6-7-17-18(8-14)29-12-28-17/h1-8,23,27H,10-12H2 Copied

Std. InChIKey:

QCHLYUQVDPRTQH-UHFFFAOYSA-N Copied
Cite this record
CSID:3662304, http://www.chemspider.com/Chemical-Structure.3662304.html (accessed 13:25, May 19, 2013) Copied

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

ACD/LogP:	3.873	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	3.83	ACD/LogD (pH 7.4):	2.95
ACD/BCF (pH 5.5):	472.61	ACD/BCF (pH 7.4):	61.19
ACD/KOC (pH 5.5):	2785.56	ACD/KOC (pH 7.4):	360.68
#H bond acceptors:	9	#H bond donors:	2
#Freely Rotating Bonds:	9	Polar Surface Area:	155.8 Å²
Index of Refraction:	1.701	Molar Refractivity:	110.807 cm³
Molar Volume:	286.303 cm³	Polarizability:	43.927 10^-24cm³
Surface Tension:	87.765998840332 dyne/cm	Density:	1.524 g/cm³
Flash Point:	393.569 °C	Enthalpy of Vaporization:	111.445 kJ/mol
Boiling Point:	727.155 °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) =  1.07

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  656.90  (Adapted Stein & Brown method)
    Melting Pt (deg C):  285.89  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  2.94E-018  (Modified Grain method)
    Subcooled liquid VP: 2.29E-015 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):  119.9
       log Kow used: 1.07 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  13186 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   8.56E-023  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.408E-020 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.07  (KowWin est)
  Log Kaw used:  -20.456  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  21.526
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.5995
   Biowin2 (Non-Linear Model)     :   0.1383
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.3189  (weeks-months)
   Biowin4 (Primary Survey Model) :   3.2888  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1264
   Biowin6 (MITI Non-Linear Model):   0.0007
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3412
 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):  3.05E-013 Pa (2.29E-015 mm Hg)
  Log Koa (Koawin est  ): 21.526
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  9.83E+006 
       Octanol/air (Koa) model:  8.24E+008 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  1 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 369.4147 E-12 cm3/molecule-sec
      Half-Life =     0.029 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =    20.847 Min
   Ozone Reaction:
      OVERALL Ozone Rate Constant =    14.103750 E-17 cm3/molecule-sec
      Half-Life =     0.081 Days (at 7E11 mol/cm3)
      Half-Life =      1.950 Hrs
   Fraction sorbed to airborne particulates (phi): 1 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  16.7
      Log Koc:  1.223 

 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 = 0.125 (BCF = 1.333)
       log Kow used: 1.07 (estimated)

 Volatilization from Water:
    Henry LC:  8.56E-023 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.429E+019  hours   (5.954E+017 days)
    Half-Life from Model Lake : 1.559E+020  hours   (6.495E+018 days)

 Removal In Wastewater Treatment:
    Total removal:               1.89  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.80  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       8.8e-007        0.512        1000       
   Water     39.8            900          1000       
   Soil      60.1            1.8e+003     1000       
   Sediment  0.0854          8.1e+003     0          
     Persistence Time: 1.07e+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	0.08
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.02
Serine Proteases	FXa, factor Xa	1f0r	0.02
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.02
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Kinases	HSP90, human heat shock protein 90	1uy6	0.01
Metalloenzymes	PDE5, phosphodiesterase 5	1xp0	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.01
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.01
Nuclear Hormone Receptors	ER, estrogen receptor; antagonist	3ert	0.01
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.00
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Other Enzymes	HIVPR, HIV protease	1hpx	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Other Enzymes	COX-1, cyclooxygenase-1	1p4g	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Kinases	TK, thymidine kinase	1kim	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Serine Proteases	Thrombin	1ba8	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Serine Proteases	Trypsin	1bju	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.00
Other Enzymes	InhA, enoyl ACP reductase	1p44	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Nuclear Hormone Receptors	GR, glucocorticoid receptor	1m2z	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00

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4-{[5-(1,3-Benzodioxol-5-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}-2-[(benzylamino)(hydroxy)methylene]-3-oxobutanenitrile

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4-{[5-(1,3-Benzodioxol-5-yl)-1,3,4-oxadiazol-2-yl]sulfanyl}-2-[(benzylamino)(hydroxy)methylene]-3-oxobutanenitrile

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