ChemSpider 2D Image | Compound C | C24H25N5O

Compound C

  • Molecular FormulaC24H25N5O
  • Average mass399.488 Da
  • Monoisotopic mass399.205902 Da
  • ChemSpider ID9698930

More details:






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

6-[4-(2-PIPERIDIN-1-YLETHOXY)PHENYL]-3-PYRIDIN-4-YLPYRAZOLO[1,5-A]PYRIMIDINE
6-{4-[2-(1-Piperidinyl)ethoxy]phenyl}-3-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin [German] [ACD/IUPAC Name]
6-{4-[2-(1-Piperidinyl)ethoxy]phenyl}-3-(4-pyridinyl)pyrazolo[1,5-a]pyrimidine [ACD/IUPAC Name]
6-{4-[2-(1-Pipéridinyl)éthoxy]phényl}-3-(4-pyridinyl)pyrazolo[1,5-a]pyrimidine [French] [ACD/IUPAC Name]
866405-64-3 [RN]
AMPK Inhibitor
Compound C
Dorsomorphin
MFCD08705402 [MDL number]
Pyrazolo[1,5-a]pyrimidine, 6-[4-[2-(1-piperidinyl)ethoxy]phenyl]-3-(4-pyridinyl)- [ACD/Index Name]
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

10K52CIC1Z [DBID]
nchembio.2007.54-comp1 [DBID]
P5499_SIGMA [DBID]
UNII:10K52CIC1Z [DBID]
  • Experimental Physico-chemical Properties
  • Miscellaneous
    • Safety:

      5 Axon Medchem 1708
      H303;H313;H317;H333;H334;H335;H373 Axon Medchem 1708
      IRRITANT Matrix Scientific 096736
      no pictogram Axon Medchem 1708
      P101;P102;P103;P260;P262;P263;P264;P270;P280;P304;P312;P340 Axon Medchem 1708
      Warning Axon Medchem 1708
    • Target Organs:

      AMPK inhibitor TargetMol T1977
    • Chemical Class:

      A pyrazolopyrimidine that is pyrazolo[1,5-<ital>a</ital>]pyrimidine which is substituted at positions 3 and 6 by pyridin-4-yl and <ital>p</ital>-[2-(piperidin-1-yl)ethoxy]phenyl groups, respectively. It is a potent, selective, reversible, and ATP-competitive inhibitor of AMPK (AMP-activated protein kinase, EC 2.7.11.31) and a selective inhibitor of bone morphogenetic protein (BMP) signaling. ChEBI CHEBI:78510
    • Bio Activity:

      AMPK MedChem Express HY-13418A
      AMPK TargetMol T1977
      Dorsomorphin(Compound C; BML-275) has been shown to act as a potent and selective inhibitor of AMPK (AMP-activated protein kinase; Ki = 109 nM), induced by AICAR and metformin; also inhibits the bone morphogenetic protein type 1 receptors ACTR-I (ALK2), BMPR-IA (ALK3), and BMPR-IB (ALK 6). MedChem Express
      Dorsomorphin(Compound C; BML-275) has been shown to act as a potent and selective inhibitor of AMPK (AMP-activated protein kinase; Ki = 109 nM), induced by AICAR and metformin; also inhibits the bone morphogenetic protein type 1 receptors ACTR-I (ALK2), BMPR-IA (ALK3), and BMPR-IB (ALK 6).; IC50 value: 109 nM (Ki for AMPK); Target: AMPK; in vitro: Compound C treatment of MCF7 cells led to Bax redistribution from the cytoplasm to mitochondria and cell death.ceramide synthase 5 (LASS/CerS 5) is involved in Compound C-induced ceramide upregulation. MedChem Express HY-13418A
      Dorsomorphin(Compound C; BML-275) has been shown to act as a potent and selective inhibitor of AMPK (AMP-activated protein kinase; Ki = 109 nM), induced by AICAR and metformin; also inhibits the bone morphogenetic protein type 1 receptors ACTR-I (ALK2), BMPR-IA (ALK3), and BMPR-IB (ALK 6).;IC50 value: 109 nM (Ki for AMPK);Target: AMPK;In vitro: Compound C treatment of MCF7 cells led to Bax redistribution from the cytoplasm to mitochondria and cell death.ceramide synthase 5 (LASS/CerS 5) is involved in Compound C-induced ceramide upregulation. Downregulation of LASS/CerS 5 was found to attenuate Compound C-mediated ceramide production, Bax redistribution, and cell death [1]. compound C prevented UPR marker glucose-regulated protein 78 (GRP78) accumulation and exerted enhanced cytotoxicity during glucose deprivation. compound C had a unique mode of action to suppress the transcriptional activation of UPR-targeted genes, as compared with the classic UPR inhibitors versipelostatin and MedChem Express HY-13418A
      PI3K/Akt/mTOR MedChem Express HY-13418A
      PI3K/Akt/mTOR Signaling TargetMol T1977
      PI3K/Akt/mTOR; MedChem Express HY-13418A

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module

Density: 1.3±0.1 g/cm3
Boiling Point:
Vapour Pressure:
Enthalpy of Vaporization:
Flash Point:
Index of Refraction: 1.670
Molar Refractivity: 118.9±0.5 cm3
#H bond acceptors: 6
#H bond donors: 0
#Freely Rotating Bonds: 6
#Rule of 5 Violations: 0
ACD/LogP: 2.39
ACD/LogD (pH 5.5): 0.09
ACD/BCF (pH 5.5): 1.00
ACD/KOC (pH 5.5): 1.47
ACD/LogD (pH 7.4): 1.70
ACD/BCF (pH 7.4): 6.06
ACD/KOC (pH 7.4): 58.99
Polar Surface Area: 56 Å2
Polarizability: 47.1±0.5 10-24cm3
Surface Tension: 51.7±7.0 dyne/cm
Molar Volume: 318.3±7.0 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) =  4.21

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  569.21  (Adapted Stein & Brown method)
    Melting Pt (deg C):  244.93  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  1.92E-012  (Modified Grain method)
    Subcooled liquid VP: 4.66E-010 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):  7.933
       log Kow used: 4.21 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  6.3477 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   2.85E-018  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.272E-013 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.21  (KowWin est)
  Log Kaw used:  -15.934  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  20.144
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.3294
   Biowin2 (Non-Linear Model)     :   0.0137
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   1.7892  (months      )
   Biowin4 (Primary Survey Model) :   3.0417  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.1116
   Biowin6 (MITI Non-Linear Model):   0.0036
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -1.0175
 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):  6.21E-008 Pa (4.66E-010 mm Hg)
  Log Koa (Koawin est  ): 20.144
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  48.3 
       Octanol/air (Koa) model:  3.42E+007 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.999 
       Mackay model           :  1 
       Octanol/air (Koa) model:  1 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant = 189.7008 E-12 cm3/molecule-sec
      Half-Life =     0.056 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.677 Hrs
   Ozone Reaction:
      No Ozone Reaction Estimation
   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    :  3.818E+005
      Log Koc:  5.582 

 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 = 2.544 (BCF = 349.8)
       log Kow used: 4.21 (estimated)

 Volatilization from Water:
    Henry LC:  2.85E-018 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 4.106E+014  hours   (1.711E+013 days)
    Half-Life from Model Lake : 4.479E+015  hours   (1.866E+014 days)

 Removal In Wastewater Treatment:
    Total removal:              40.46  percent
    Total biodegradation:        0.40  percent
    Total sludge adsorption:    40.06  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       4.09e-008       1.35         1000       
   Water     8.2             1.44e+003    1000       
   Soil      87.7            2.88e+003    1000       
   Sediment  4.09            1.3e+004     0          
     Persistence Time: 2.98e+003 hr




                    

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