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Enalaprilat
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[ CAS No. 76420-72-9 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 76420-72-9
Chemical Structure| 76420-72-9
Structure of 76420-72-9 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 76420-72-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 76420-72-9 ]

SDS Specification
Alternatived Products of [ 76420-72-9 ]

Product Details of [ 76420-72-9 ]

CAS No. :76420-72-9 MDL No. :MFCD00865786
Formula : C18H24N2O5 Boiling Point : -
Linear Structure Formula :- InChI Key :LZFZMUMEGBBDTC-QEJZJMRPSA-N
M.W : 348.39 Pubchem ID :5462501
Synonyms :
MK-422 anhydrous
Chemical Name :(S)-1-((S)-2-(((S)-1-Carboxy-3-phenylpropyl)amino)propanoyl)pyrrolidine-2-carboxylic acid

Calculated chemistry of [ 76420-72-9 ]

Physicochemical Properties

Num. heavy atoms : 25
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 9
Num. H-bond acceptors : 6.0
Num. H-bond donors : 3.0
Molar Refractivity : 95.53
TPSA : 106.94 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.95 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.87
Log Po/w (XLOGP3) : -0.74
Log Po/w (WLOGP) : 0.75
Log Po/w (MLOGP) : -1.35
Log Po/w (SILICOS-IT) : 1.26
Consensus Log Po/w : 0.36

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.12
Solubility : 26.6 mg/ml ; 0.0763 mol/l
Class : Very soluble
Log S (Ali) : -1.03
Solubility : 32.6 mg/ml ; 0.0935 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.62
Solubility : 0.843 mg/ml ; 0.00242 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.2

Safety of [ 76420-72-9 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P305+P351+P338-P304+P340-P405 UN#:
Hazard Statements:H302 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 76420-72-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 76420-72-9 ]

[ 76420-72-9 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 76095-16-4 ]
  • [ 76420-72-9 ]
Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 2816 - 2819
[2]European Journal of Pharmacology,2006,vol. 537,p. 31 - 36
  • 2
  • [ 76420-72-9 ]
  • [ 84023-58-5 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride for 24h; Heating;
Reference： [1]Drummer; Kourtis [Arzneimittel-Forschung/Drug Research, 1987, vol. 37, # 11, p. 1225 - 1228]
  • 3
  • [ 75847-73-3 ]
  • [ 76420-72-9 ]
YieldReaction ConditionsOperation in experiment
75% With sodium hydroxide for 24h; Ambient temperature;
at 37℃; esterase from various rat tissue homogenates or plasma;
With recombinant human carboxylesterase 1; water In aq. phosphate buffer at 37℃; for 0.333333h; Enzymatic reaction; Kinetic Studies General procedure: Michaelis-Menten kinetic parameters were determined forTPL, RPL, and EPL in recombinant human CES1. An initial study wasperformed to establish time and protein linearity of the reactions by measuringproduct formed at several time points (5, 10, 15, 20, and 30 minutes) usingthree protein concentrations (50, 100, and 150 mg/ml). Final protein andsubstrate concentrations, as well as incubation times, were selected such thata quantifiable amount of hydrolysis product was formed and so that thesampling was done in the linear range of the reactions. No more than 20% ofsubstrate was hydrolyzed at the time of sampling. Substrate concentrationswere 0.2-4 mM for TPL, 0.1-4 mM for RPL, and 0.05-4 mM for EPL. Finalrecombinant CES1 protein concentrations were 50 mg/ml for TPL and RPL,and 100 mg/ml for EPL. No organic solvent was present in the incubations. Thedrug and enzyme combinations were incubated in 96-well, twin.tec polymerasechain reaction plates (Eppendorf, Hamburg, Germany) in 100 mM phosphatebuffer at 37°C, in a final reaction volume of 50 ml. Control incubations with noenzyme were performed for each compound. Reactions (8 minutes for RPL,10 minutes for TPL, and 20 minutes for EPL) were terminated by transferring20 ml to an equal volume of cold acetonitrile with 0.5% formic acid and thecorresponding internal standard-500 nM trandolaprilat (TPLA)-d5 for TPL orRPL, and 1,000 nM enalaprilat (EPLA)-d5 for EPL. Next, 110 ml of mobilephase was added, and the samples were centrifuged at 2,000g, 5°C, for10 minutes. The supernatant was analyzed by liquid chromatography-tandemmass spectrometry as described in the analytical methods section below. Thehydrolysis rate versus the substrate concentration was plotted and fit witha standard Michaelis-Menten equation or a substrate inhibition equation, wherea second substrate molecule was treated as an uncompetitive inhibitor (Cornish-Bowden, 2012). The two fits were compared with an extra-sum-of-squaresF-test. The test compares the improvement of sum-of-squares with the morecomplicated model (the substrate inhibition model) versus the loss of degrees offreedom. The null-hypothesis was that the data were adequately described bythe standard Michaelis-Menten equation. P values , 0.05 were consideredsignificant. Nonlinear regression fitting and statistical analysis was performedwith Prism, version 6.02 (GraphPad Software, Inc., San Diego, CA). Intrinsicclearance (CLint) was calculated by dividing Vmax by Km.
Reference： [1]Iwasaki; Kimura; Numao; Kondo [Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 2, p. 280 - 283]
[2]Tabata; Yamazaki; Ohtake; Hayashi [Arzneimittel-Forschung/Drug Research, 1990, vol. 40, # 8, p. 865 - 867]
[3]Thomsen, Ragnar; Rasmussen, Henrik B.; Linnet, Kristian [Drug Metabolism and Disposition, 2014, vol. 42, # 1, p. 126 - 133]
  • 4
  • [ 108428-39-3 ]
  • [ 76420-72-9 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; trifluoroacetic acid Multistep reaction;
Multi-step reaction with 2 steps 1: 85 percent / TFA / 3 h / Ambient temperature 2: 75 percent / 1N NaOH / 24 h / Ambient temperature
Reference： [1]Iwasaki, Genji; Kimura, Rieko; Numao, Naganori; Kondo, Kiyoshi [Chemistry Letters, 1988, # 10, p. 1691 - 1694]
[2]Iwasaki; Kimura; Numao; Kondo [Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 2, p. 280 - 283]
  • 5
  • [ 104-53-0 ]
  • [ 76420-72-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 45 percent / methanol; H2O / 8 h / 70 °C 2: 99.3 percent / NH4Cl / aq. NH3 / 50 h / 37 °C / enzymatic hydrolysis with Pseudomonas putida at pH 9 3: 1.) NaNO2, 2N H2SO4; 2.) KBr, NaNO2, 3N H2SO4 / 1.) 50percent CH3COOH, r.t., 24 h; 2.) 50percent CH3COOH, 0-5 deg C, 1 h 4: 95 percent / SOCl2 / 24 h / Ambient temperature 5: 74 percent / (NH4)2CO3 / nitromethane; H2O / 96 h / 50 °C 6: 85 percent / TFA / 3 h / Ambient temperature 7: 75 percent / 1N NaOH / 24 h / Ambient temperature
Reference： [1]Iwasaki; Kimura; Numao; Kondo [Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 2, p. 280 - 283]
  • 6
  • [ 120379-81-9 ]
  • [ 76420-72-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 99.3 percent / NH4Cl / aq. NH3 / 50 h / 37 °C / enzymatic hydrolysis with Pseudomonas putida at pH 9 2: 1.) NaNO2, 2N H2SO4; 2.) KBr, NaNO2, 3N H2SO4 / 1.) 50percent CH3COOH, r.t., 24 h; 2.) 50percent CH3COOH, 0-5 deg C, 1 h 3: 95 percent / SOCl2 / 24 h / Ambient temperature 4: 74 percent / (NH4)2CO3 / nitromethane; H2O / 96 h / 50 °C 5: 85 percent / TFA / 3 h / Ambient temperature 6: 75 percent / 1N NaOH / 24 h / Ambient temperature
Reference： [1]Iwasaki; Kimura; Numao; Kondo [Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 2, p. 280 - 283]
  • 7
  • [ 121842-76-0 ]
  • [ 76420-72-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 95 percent / SOCl2 / 24 h / Ambient temperature 2: 74 percent / (NH4)2CO3 / nitromethane; H2O / 96 h / 50 °C 3: 85 percent / TFA / 3 h / Ambient temperature 4: 75 percent / 1N NaOH / 24 h / Ambient temperature
Reference： [1]Iwasaki; Kimura; Numao; Kondo [Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 2, p. 280 - 283]
  • 8
  • [ 121842-77-1 ]
  • [ 76420-72-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 74 percent / (NH4)2CO3 / nitromethane; H2O / 96 h / 50 °C 2: 85 percent / TFA / 3 h / Ambient temperature 3: 75 percent / 1N NaOH / 24 h / Ambient temperature
Reference： [1]Iwasaki; Kimura; Numao; Kondo [Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 2, p. 280 - 283]
  • 9
  • [ 121842-75-9 ]
  • [ 76420-72-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1.) NaNO2, 2N H2SO4; 2.) KBr, NaNO2, 3N H2SO4 / 1.) 50percent CH3COOH, r.t., 24 h; 2.) 50percent CH3COOH, 0-5 deg C, 1 h 2: 95 percent / SOCl2 / 24 h / Ambient temperature 3: 74 percent / (NH4)2CO3 / nitromethane; H2O / 96 h / 50 °C 4: 85 percent / TFA / 3 h / Ambient temperature 5: 75 percent / 1N NaOH / 24 h / Ambient temperature
Reference： [1]Iwasaki; Kimura; Numao; Kondo [Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 2, p. 280 - 283]
  • 10
  • [ 710-11-2 ]
  • [ 76420-72-9 ]
Reference： [1]Chemistry Letters,1988,p. 1691 - 1694
  • 11
  • [ 29375-30-2 ]
  • [ 76420-72-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1.) molecular sieves, sodium acetate, catecholborane / 1.) CH2Cl2, -15 - 0 deg C, 1 h.; 2.) CH2Cl2 2: 1.) TFA; 2.) 1M NaOH
Reference： [1]Iwasaki, Genji; Kimura, Rieko; Numao, Naganori; Kondo, Kiyoshi [Chemistry Letters, 1988, # 10, p. 1691 - 1694]
  • 12
  • [ 84793-24-8 ]
  • [ 147-85-3 ]
  • [ 82717-96-2 ]
  • [ 76420-72-9 ]
  • [ 75847-73-3 ]
  • [ 115729-52-7 ]
Reference： [1]Patent: US6335453,2002,B1 .Location in patent: Example 1
[2]Patent: US6335453,2002,B1 .Location in patent: Example 14
[3]Patent: US6335453,2002,B1 .Location in patent: Example 3
[4]Patent: US6335453,2002,B1 .Location in patent: Example 4
[5]Patent: US6335453,2002,B1 .Location in patent: Example 4
[6]Patent: US6335453,2002,B1 .Location in patent: Example 2
  • 13
  • [ 76095-16-4 ]
  • [ 256510-64-2 ]
  • [ 76420-72-9 ]
Reference： [1]Journal of Mass Spectrometry,2011,vol. 46,p. 1269 - 1273
YieldReaction ConditionsOperation in experiment
With tris-(2-carboxyethyl)-phosphine hydrochloride; sodium chloride; sodium hydroxide In aq. buffer at 25℃;
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