InChI=1/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3

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Inherent Properties, Identifiers and References

ChemSpider ID:	2114
Empirical Formula:	C₁₄H₁₉NO₄
Molecular Weight:	265.305
Nominal Mass:	265 Da
Average Mass:	265.305 Da
Monoisotopic Mass:	265.131408 Da

Systematic Name:

[4-hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl] acetate

SMILES:

O=C(OC1C(NCC1O)Cc2ccc(OC)cc2)C

InChI:

InChI=1/C14H19NO4/c1-9(16)19-14-12(15-8-13(14)17)7-10-3-5-11(18-2)6-4-10/h3-6,12-15,17H,7-8H2,1-2H3

InChIKey:

YKJYKKNCCRKFSL-UHFFFAOYAE

Original Reference(s)

Data Source	External ID(s)
ChemDB	3965463
DiscoveryGate	2199
DTP/NCI	147340
Nature Chemical Biology	nchembio.2007.59-comp2
NIST	2218570164
PubChem	2199
Single Depositions	O=C(OC1C(NCC1O)Cc2ccc(OC)cc2)C
SSH DS	N/A
Thomson Pharma	00018357

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Supplemental Information

Links & References

Krutzik et al.. High-content single cell drug screening with phospho-specific flow cytometry, Nature Chemical Biology, doi: 10.1038/nchembio.2007.59, published online 23 December 2007.

[DOI: 10.1038/nchembio.2007.59]

Names and Synonyms

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

[4-Hydroxy-2-[(4-methoxyphenyl)methyl]pyrrolidin-3-yl] acetate

Database ID(s)

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

nchembio.2007.59-comp2

Predicted Properties

LogP:	ACD/LogP: 0.42 XLogP: 0.80 ALOGPS: 0.97	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	-2.28	ACD/LogD (pH 7.4):	-0.63
ACD/BCF (pH 5.5):	1	ACD/BCF (pH 7.4):	1
ACD/KOC (pH 5.5):	1	ACD/KOC (pH 7.4):	3.6
#H bond acceptors:	5	#H bond donors:	2
#Freely Rotating Bonds:	6	Polar Surface Area:	48 Å²
Index of Refraction:	1.557	Molar Refractivity:	70.46 cm³
Molar Volume:	218.6 cm³	Polarizability:	27.93 10^-24cm³
Surface Tension:	48.7 dyne/cm	Density:	1.21 g/cm³
Flash Point:	194.9 °C	Enthalpy of Vaporization:	68.48 kJ/mol
Boiling Point:	398.7 °C at 760 mmHg	Vapour Pressure:	4.5E-07 mmHg at 25°C

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  0.61

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  384.94  (Adapted Stein & Brown method)
    Melting Pt (deg C):  144.87  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.48E-008  (Modified Grain method)
    MP  (exp database):  140.5 deg C
    Subcooled liquid VP: 5.1E-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):  5.965e+004
       log Kow used: 0.61 (estimated)
       no-melting pt equation used
     Water Sol (Exper. database match) =  6550 mg/L (28 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.1109e+005 mg/L
    Wat Sol (Exper. database match) =  6550.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aliphatic Amines
       Esters

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   7.13E-015  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.037E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.61  (KowWin est)
  Log Kaw used:  -12.535  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  13.145
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.2946
   Biowin2 (Non-Linear Model)     :   0.9998
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8045  (weeks       )
   Biowin4 (Primary Survey Model) :   3.8752  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.6913
   Biowin6 (MITI Non-Linear Model):   0.4008
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.8317
 Ready Biodegradability Prediction:   YES

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  6.8E-005 Pa (5.1E-007 mm Hg)
  Log Koa (Koawin est  ): 13.145
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.0441 
       Octanol/air (Koa) model:  3.43 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.614 
       Mackay model           :  0.779 
       Octanol/air (Koa) model:  0.996 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 125.2463 E-12 cm3/molecule-sec
      Half-Life =     0.085 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.025 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 0.697 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  55.02
      Log Koc:  1.741 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.805E-003  L/mol-sec
  Kb Half-Life at pH 8:       7.829  years  
  Kb Half-Life at pH 7:      78.287  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 0.61 (estimated)

 Volatilization from Water:
    Henry LC:  7.13E-015 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.338E+011  hours   (5.573E+009 days)
    Half-Life from Model Lake : 1.459E+012  hours   (6.08E+010 days)

 Removal In Wastewater Treatment:
    Total removal:               1.86  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.77  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       4.41e-007       2.05         1000       
   Water     37              360          1000       
   Soil      63              720          1000       
   Sediment  0.0702          3.24e+003    0          
     Persistence Time: 593 hr

SimBioSys LASSO

Descriptors: 0, 0, 0, 1, 0, 0, 0, 5, 1, 0, 1, 2, 5, 4, 8, 0, 6, 2, 1, 0, 0, 0, 0, 0

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
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
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	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	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Kinases	TK, thymidine kinase	1kim	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Kinases	HSP90, human heat shock protein 90	1uy6	0.00
Serine Proteases	Thrombin	1ba8	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.00
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00