Inherent Properties, Identifiers and References
ChemSpider ID: 3933
Empirical Formula: C7H7NO3
Molecular Weight: 153.1354
Nominal Mass: 153 Da
Average Mass: 153.1354 Da
Monoisotopic Mass: 153.042593 Da
Quick Links: Permalink Similar Isomers
Systematic Name: 5-amino-2-hydroxy-benzoic acid
SMILES: O=C(O)c1cc(ccc1O)N
InChI: InChI=1/C7H7NO3/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,9H,8H2,(H,10,11)
InChIKey: KBOPZPXVLCULAV-UHFFFAOYAE
(Details...) Wikipedia Article(s)
Mesalazine (INN, BAN), also known as Mesalamine (USAN) or 5-aminosalicylic acid (5-ASA), is an anti-inflammatory drug used to treat inflammation of the digestive tract (Crohn's disease) and mild to moderate ulcerative colitis. Mesalazine is a bowel-specific aminosalicylate drug that is metabolized in the gut and has its predominant actions there, thereby having fewer systemic side effects. As a derivative of salicylic acid, 5-ASA is also an antioxidant that traps free radicals, which are potentially damaging by-products of metabolism. 5-ASA is considered the active moiety of sulfasalazine, which is metabolized to it. Read more... or Edit at Wikipedia...
(Details...) Original Reference(s)
Data Source External ID(s)
Molbank Molecules 2001 Volume 6 Page M260
Disclaimer (Details...) Supplemental Information

User Data

  • experimental physchem properties
    • Melting Point: ca 280 dec.
  • miscellaneous
    • Appearance: light tan to grey powder
    • Stability: Stable. Incompatible with acids, acid anhydrides,acid chlorides, chloroformates, strong oxidizing agents.
    • Toxicity: ORL-RAT LD50 2800 mg kg-1, IPR-RAT LD50 1000 mg kg-1, ORL-MUS LD50 5000 mg kg-1, IPR-MUS LD50 681 mg kg-1, SKN-RBT LD50 > 5000 mg kg-1
    • Safety: WARNING: Irreversible damage risk, protect skin/eyes/lungs.
    • Safety: Safety glasses.
(Details...) Names and Synonyms

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

2-Hydroxy​-5-aminob​enzoic ac​id

3-carboxy​-4-hydrox​yaniline

4-14-00-0​2058 (Bei​lstein Ha​ndbook Re​ference) [Beilstein]

5-Amino-2​-hydroxyb​enzene-1-​carboxyli​c Acid

5-Amino-2​-hydroxyb​enzolcarb​onsäure

acide 5-a​mino-2-hy​droxybenz​oïque

Asacolitin

Asacolon

Fisalamine

Lixacol

More...
(Details...) Database ID(s)

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

09409_FLU​KA

09410_FLU​KA

A3537_SIG​MA

A3613/015​3179

A6178_SIG​MA

A79809_AL​DRICH

AI3-15564

BRN 20904​21

CCRIS 7334

D00377

More...
(Details...) Predicted Properties
LogP: ACD/LogP: 0.46
ALOGPS: 0.75
# of Rule of 5 Violations: 0
ACD/LogD (pH 5.5): -2.19 ACD/LogD (pH 7.4): -2.67
ACD/BCF (pH 5.5): 1 ACD/BCF (pH 7.4): 1
ACD/KOC (pH 5.5): 1 ACD/KOC (pH 7.4): 1
#H bond acceptors: 4 #H bond donors: 4
#Freely Rotating Bonds: 3 Polar Surface Area: 38.77 Å2
Index of Refraction: 1.691 Molar Refractivity: 39.3 cm3
Molar Volume: 102.6 cm3 Polarizability: 15.57 10-24cm3
Surface Tension: 83.3 dyne/cm Density: 1.491 g/cm3
Flash Point: 198.1 °C Enthalpy of Vaporization: 69.09 kJ/mol
Boiling Point: 403.9 °C at 760 mmHg Vapour Pressure: 3.01E-07 mmHg at 25°C
(Details...) MeSH

MeSH Descriptor Data

MeSH Heading Mesalamine
Concept 1 (Preferred) Mesalamine
Scope Note An anti-inflammatory agent, structurally related to the SALICYLATES, which is active in INFLAMMATORY BOWEL DISEASE. It is considered to be the active moiety of SULPHASALAZINE. (From Martindale, The Extra Pharmacopoeia, 30th ed)
Term Mesalamine
Term Mesalazine
Term 5-Aminosalicylate
Allowable Qualifiers AD AE AN AI BL CF CS CL DU EC HI IM IP ME PK PD PO RE ST SD TU TO UR CH CT AG
Pharm. Action Anti-Inflammatory Agents, Non-Steroidal
Registry Number 89-57-6
Date of Entry 1997/06/20
Established Date 1998/01/01
Revision Date 2005/06/30

MeSH Tree Structures

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  0.98

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  346.34  (Adapted Stein & Brown method)
    Melting Pt (deg C):  128.86  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.1E-008  (Modified Grain method)
    MP  (exp database):  283 deg C
    Subcooled liquid VP: 4.37E-005 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):  1.077e+004
       log Kow used: 0.98 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  888.84 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Aromatic Amines-acid
       Phenols-acid
       Salicylic Acid-acid

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.02E-012  atm-m3/mole
   Group Method:   2.28E-015  atm-m3/mole
 Henrys LC [VP/WSol estimate using EPI values]:  1.141E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.98  (KowWin est)
  Log Kaw used:  -9.688  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  10.668
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.7336
   Biowin2 (Non-Linear Model)     :   0.9053
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.8701  (weeks       )
   Biowin4 (Primary Survey Model) :   3.5659  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.5647
   Biowin6 (MITI Non-Linear Model):   0.5429
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.6183
 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):  0.00583 Pa (4.37E-005 mm Hg)
  Log Koa (Koawin est  ): 10.668
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.000515 
       Octanol/air (Koa) model:  0.0114 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.0183 
       Mackay model           :  0.0396 
       Octanol/air (Koa) model:  0.478 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  20.8772 E-12 cm3/molecule-sec
      Half-Life =     0.512 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     6.148 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   Reaction With Nitrate Radicals May Be Important!
   Fraction sorbed to airborne particulates (phi): 0.0289 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  10
      Log Koc:  1.000 

 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 = 0.500 (BCF = 3.162)
       log Kow used: 0.98 (estimated)

 Volatilization from Water:
    Henry LC:  5.02E-012 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.443E+008  hours   (6.014E+006 days)
    Half-Life from Model Lake : 1.575E+009  hours   (6.56E+007 days)

 Removal In Wastewater Treatment:
    Total removal:               1.88  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.79  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       0.000269        12.3         1000       
   Water     34.7            360          1000       
   Soil      65.2            720          1000       
   Sediment  0.0693          3.24e+003    0          
     Persistence Time: 608 hr