InChI=1/C8H9NO2/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5H,9H2,1H3

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Search term: LZXXNPOYQCLXRS-UHFFFAOYAA
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Inherent Properties, Identifiers and References

ChemSpider ID:	11585
Empirical Formula:	C₈H₉NO₂
Molecular Weight:	151.1626
Nominal Mass:	151 Da
Average Mass:	151.1626 Da
Monoisotopic Mass:	151.063329 Da

Systematic Name:

SMILES:

O=C(OC)c1ccc(N)cc1

InChI:

InChI=1/C8H9NO2/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5H,9H2,1H3

InChIKey:

LZXXNPOYQCLXRS-UHFFFAOYAA

Std. InChI:

InChI=1S/C8H9NO2/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5H,9H2,1H3

Std. InChIKey:

LZXXNPOYQCLXRS-UHFFFAOYSA-N

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Links & References

Igor V. Tetko, Vsevolod Yu. Tanchuk, Tamara N. Kasheva, and Alessandro E. P. Villa. Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices, J. Chem. Inf. Comput. Sci., 2001, 41 (6), pp 1488–1493

[DOI: 10.1021/ci000392t]

The molecular weight and electrotopological E-state indices were used to estimate by Artificial Neural Networks aqueous solubility for a diverse set of 1291 organic compounds. The neural network with 33-4-1 neurons provided highly predictive results with r2 = 0.91 and RMS = 0.62.

Philip Prathipati, Ngai Ling Ma* and Thomas H. Keller. Global Bayesian Models for the Prioritization of Antitubercular Agents, J. Chem. Inf. Model., 2008, 48 (12), pp 2362–2370

[DOI: 10.1021/ci800143n]

E. L. Willighagen, H. M. G. W. Denissen, R. Wehrens, and L. M. C. Buydens. On the Use of 1H and 13C 1D NMR Spectra as QSPR Descriptors, J. Chem. Inf. Model., 46 (2), 487-494, 2006

[PubMed: 16562976] [DOI: 10.1021/ci050282s]

A.C. Doriguetto, C.H.T. De Paula Silva, D.G. Rando, E.I. Ferreira, J. Ellena. A new monoclinic polymorph of methyl p-aminobenzoate, Acta Cryst C 2004 Volume 60 Part 1 Page o69-o71

User Data

experimental physchem properties

Melting Point: 111-113

The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. See also: Melting Point

Solubility: -1.59

No description available

miscellaneous

Safety: WARNING: Irritates lungs, eyes, skin

See Chemical Safety

Names and Synonyms

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

benzoic acid, 4-amino-, methyl ester

Methyl 4-aminobenzoate

Methyl-4-aminobenzolcarboxylat

210-598-7 [EINECS/ELINCS]

4-(Carbomethoxyl)aniline

4-(Methoxycarbonyl)aniline

4-14-00-01128 (Beilstein Handbook Reference) [Beilstein]

4-Aminobenzoic Acid Methyl Ester

4-Carbomethoxyaniline

619-45-4 [RN]

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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:	1.41	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	1.41	ACD/LogD (pH 7.4):	1.41
ACD/BCF (pH 5.5):	6.99	ACD/BCF (pH 7.4):	6.99
ACD/KOC (pH 5.5):	139.88	ACD/KOC (pH 7.4):	140.01
#H bond acceptors:	3	#H bond donors:	2
#Freely Rotating Bonds:	3	Polar Surface Area:	29.54 Å²
Index of Refraction:	1.565	Molar Refractivity:	42.26 cm³
Molar Volume:	129.6 cm³	Polarizability:	16.75 10^-24cm³
Surface Tension:	46.2 dyne/cm	Density:	1.166 g/cm³
Flash Point:	154.9 °C	Enthalpy of Vaporization:	53.92 kJ/mol
Boiling Point:	299.2 °C at 760 mmHg	Vapour Pressure:	0.00121 mmHg at 25°C

MeSH

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  1.31
    Log Kow (Exper. database match) =  1.37
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  263.57  (Adapted Stein & Brown method)
    Melting Pt (deg C):  55.76  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.00193  (Modified Grain method)
    MP  (exp database):  110-111 deg C
    Subcooled liquid VP: 0.0132 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):  5070
       log Kow used: 1.37 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  3820 mg/L (37 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  5709 mg/L
    Wat Sol (Exper. database match) =  3820.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.23E-008  atm-m3/mole
   Group Method:   7.39E-009  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  7.572E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.37  (exp database)
  Log Kaw used:  -6.299  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.669
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6160
   Biowin2 (Non-Linear Model)     :   0.9541
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8704  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7502  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4817
   Biowin6 (MITI Non-Linear Model):   0.4704
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2688
 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):  1.76 Pa (0.0132 mm Hg)
  Log Koa (Koawin est  ): 7.669
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.7E-006 
       Octanol/air (Koa) model:  1.15E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  6.16E-005 
       Mackay model           :  0.000136 
       Octanol/air (Koa) model:  0.000916 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  34.8020 E-12 cm3/molecule-sec
      Half-Life =     0.307 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.688 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 9.9E-005 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  20.98
      Log Koc:  1.322 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.540E-003  L/mol-sec
  Kb Half-Life at pH 8:       8.648  years  
  Kb Half-Life at pH 7:      86.475  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.355 (BCF = 2.264)
       log Kow used: 1.37 (expkow database)

 Volatilization from Water:
    Henry LC:  7.39E-009 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River: 9.741E+004  hours   (4059 days)
    Half-Life from Model Lake : 1.063E+006  hours   (4.428E+004 days)

 Removal In Wastewater Treatment:
    Total removal:               1.94  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.85  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       0.133           7.38         1000       
   Water     32.1            360          1000       
   Soil      67.7            720          1000       
   Sediment  0.0718          3.24e+003    0          
     Persistence Time: 578 hr


 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  1.31
    Log Kow (Exper. database match) =  1.37
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  263.57  (Adapted Stein & Brown method)
    Melting Pt (deg C):  55.76  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  0.00193  (Modified Grain method)
    MP  (exp database):  110-111 deg C
    Subcooled liquid VP: 0.0132 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):  5070
       log Kow used: 1.37 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  3820 mg/L (37 deg C)
        Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  5709 mg/L
    Wat Sol (Exper. database match) =  3820.00
       Exper. Ref:  YALKOWSKY,SH & DANNENFELSER,RM (1992)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.23E-008  atm-m3/mole
   Group Method:   7.39E-009  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  7.572E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  1.37  (exp database)
  Log Kaw used:  -6.299  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  7.669
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.6160
   Biowin2 (Non-Linear Model)     :   0.9541
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8704  (weeks       )
   Biowin4 (Primary Survey Model) :   3.7502  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.4817
   Biowin6 (MITI Non-Linear Model):   0.4704
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.2688
 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):  1.76 Pa (0.0132 mm Hg)
  Log Koa (Koawin est  ): 7.669
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  1.7E-006 
       Octanol/air (Koa) model:  1.15E-005 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  6.16E-005 
       Mackay model           :  0.000136 
       Octanol/air (Koa) model:  0.000916 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  34.8020 E-12 cm3/molecule-sec
      Half-Life =     0.307 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     3.688 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Fraction sorbed to airborne particulates (phi): 9.9E-005 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  20.98
      Log Koc:  1.322 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  2.540E-003  L/mol-sec
  Kb Half-Life at pH 8:       8.648  years  
  Kb Half-Life at pH 7:      86.475  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.355 (BCF = 2.264)
       log Kow used: 1.37 (expkow database)

 Volatilization from Water:
    Henry LC:  7.39E-009 atm-m3/mole  (estimated by Group SAR Method)
    Half-Life from Model River: 9.741E+004  hours   (4059 days)
    Half-Life from Model Lake : 1.063E+006  hours   (4.428E+004 days)

 Removal In Wastewater Treatment:
    Total removal:               1.94  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.85  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       0.133           7.38         1000       
   Water     32.1            360          1000       
   Soil      67.7            720          1000       
   Sediment  0.0718          3.24e+003    0          
     Persistence Time: 578 hr

SimBioSys LASSO

Descriptors: 0, 0, 0, 2, 0, 0, 0, 2, 1, 0, 0, 0, 0, 4, 3, 0, 6, 2, 1, 1, 0, 0, 0, 0

Category	Target	PDB Code	LASSO Score
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.04
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.01
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Other Enzymes	InhA, enoyl ACP reductase	1p44	0.01
Nuclear Hormone Receptors	PR, progesterone receptor	1sr7	0.01
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.00
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.00
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Other Enzymes	HIVPR, HIV protease	1hpx	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	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	NA, neuraminidase	1a4g	0.00
Other Enzymes	COX-1, cyclooxygenase-1	1p4g	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Serine Proteases	Thrombin	1ba8	0.00
Kinases	HSP90, human heat shock protein 90	1uy6	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Kinases	TK, thymidine kinase	1kim	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Other Enzymes	AChE, acetylcholinesterase	1eve	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00