ChemSpider 2D Image | CHIR090 | C24H27N3O5

CHIR090

  • Molecular FormulaC24H27N3O5
  • Average mass437.488 Da
  • Monoisotopic mass437.195068 Da
  • ChemSpider ID9721399

  • defined stereocentres - 2 of 2 defined stereocentres

More details:

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(2S,3R)-N,3-dihydroxy-2-[(4-{2-[4-(morpholin-4-ylmethyl)phenyl]ethynyl}phenyl)formamido]butanamide
(2S,3R)-N,3-dihydroxy-2-{[4-(2-{4-[(morpholin-4-yl)methyl]phenyl}ethynyl)phenyl]formamido}butanamide
728865-23-4 [RN]
Benzamide, N-[(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl]-4-[2-[4-(4-morpholinylmethyl)phenyl]ethynyl]- [ACD/Index Name]
CHIR090
CHIR-090
N-[(2S,3R)-3-Hydroxy-1-(hydroxyamino)-1-oxo-2-butanyl]-4-{[4-(4-morpholinylmethyl)phenyl]ethinyl}benzamid [German] [ACD/IUPAC Name]
N-[(2S,3R)-3-Hydroxy-1-(hydroxyamino)-1-oxo-2-butanyl]-4-{[4-(4-morpholinylmethyl)phenyl]ethynyl}benzamide [ACD/IUPAC Name]
N-[(2S,3R)-3-Hydroxy-1-(hydroxyamino)-1-oxo-2-butanyl]-4-{[4-(4-morpholinylméthyl)phényl]éthynyl}benzamide [French] [ACD/IUPAC Name]
N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}-4-{[4-(morpholin-4-ylmethyl)phenyl]ethynyl}benzamide
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

PubChem Substance ID 329825761 [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Chemical Class:

      An <stereo>L</stereo>-threonine derivative obtained by formal condensation of the carboxy group of 4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)benzoic acid with the amino group of <element>N</element >-hydroxy-<stereo>L</stereo>-threoninamide. ChEBI CHEBI:134107
      An L-threonine derivative obtained by formal condensation of the carboxy group of 4-({4-[(morpholin-4-yl)methyl]phenyl}ethynyl)benzoic acid with the amino group of N-hydroxy-L-threoninamide. ChEBI https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:134107, CHEBI:134107

    • Bio Activity:

      Antibacterial MedChem Express HY-15460
      Anti-infection; MedChem Express HY-15460
      CHIR-090 is a potent LpxC inhibitor, displays two-step time-dependent inhibition and kills a wide range of Gram-negative pathogens as effectively as ciprofloxacin or tobramycin. MedChem Express
      CHIR-090 is a potent LpxC inhibitor, displays two-step time-dependent inhibition and kills a wide range of Gram-negative pathogens as effectively as ciprofloxacin or tobramycin.;IC50 value:;Target: LpxC; Antibacterial; LpxC;The UDP-3-O-(R-3-hydroxyacyl)-N-acetylglucosamine deacetylase LpxC is an essential enzyme of lipid A biosynthesis in Gram-negative bacteria and a promising antibiotic target. MedChem Express HY-15460

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.3±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.650
Molar Refractivity: 119.2±0.4 cm3
#H bond acceptors: 8
#H bond donors: 4
#Freely Rotating Bonds: 8
#Rule of 5 Violations: 0
ACD/LogP: 1.23
ACD/LogD (pH 5.5): 0.25
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 12.61
ACD/LogD (pH 7.4): 1.11
ACD/BCF (pH 7.4): 3.99
ACD/KOC (pH 7.4): 91.24
Polar Surface Area: 111 Å2
Polarizability: 47.2±0.5 10-24cm3
Surface Tension: 70.4±5.0 dyne/cm
Molar Volume: 326.6±5.0 cm3

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™ 

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  0.85

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  725.29  (Adapted Stein & Brown method)
    Melting Pt (deg C):  317.84  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.22E-021  (Modified Grain method)
    Subcooled liquid VP: 2.41E-018 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):  333.8
       log Kow used: 0.85 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1e+006 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.22E-025  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.104E-024 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  0.85  (KowWin est)
  Log Kaw used:  -23.302  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  24.152
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3555
   Biowin2 (Non-Linear Model)     :   0.0064
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.0746  (months      )
   Biowin4 (Primary Survey Model) :   3.2537  (days-weeks  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.3970
   Biowin6 (MITI Non-Linear Model):   0.0005
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -2.5932
 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):  3.21E-016 Pa (2.41E-018 mm Hg)
  Log Koa (Koawin est  ): 24.152
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  9.34E+009 
       Octanol/air (Koa) model:  3.48E+011 
   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 = 225.0398 E-12 cm3/molecule-sec
      Half-Life =     0.048 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.570 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =     0.432000 E-17 cm3/molecule-sec
      Half-Life =     2.653 Days (at 7E11 mol/cm3)
      Half-Life =     63.667 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    :  3551
      Log Koc:  3.550 

 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: 0.85 (estimated)

 Volatilization from Water:
    Henry LC:  1.22E-025 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.004E+022  hours   (4.182E+020 days)
    Half-Life from Model Lake : 1.095E+023  hours   (4.563E+021 days)

 Removal In Wastewater Treatment:
    Total removal:               1.87  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.78  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       1.24e-006       1.12         1000       
   Water     44.9            1.44e+003    1000       
   Soil      55              2.88e+003    1000       
   Sediment  0.0934          1.3e+004     0          
     Persistence Time: 1.25e+003 hr

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