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Inherent Properties, Identifiers and References
ChemSpider ID: 4514933
Empirical Formula: C21H31N3O5
Molecular Weight: 405.4879
Nominal Mass: 405 Da
Average Mass: 405.4879 Da
Monoisotopic Mass: 405.226371 Da
Systematic Name: (2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenyl-propyl]amino]hex​anoyl]pyrrolidine-2-carboxylic acid
SMILES: O=C(O)[C@H]2N(C(=O)[C@@H](N[C@H](C(=O)O)CCc1ccccc1)CCCCN)CCC2
InChI: InChI=1/C21H31N3O5/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)2​9)23-17(20(26)27)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18,23H,4-6,9-1​4,22H2,(H,26,27)(H,28,29)/t16-,17-,18-/m0/s1
InChIKey: RLAWWYSOJDYHDC-BZSNNMDCBR
Std. InChI: InChI=1S/C21H31N3O5/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)​29)23-17(20(26)27)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18,23H,4-6,9-​14,22H2,(H,26,27)(H,28,29)/t16-,17-,18-/m0/s1
Std. InChIKey: RLAWWYSOJDYHDC-BZSNNMDCSA-N
(Details...) Wikipedia Article(s)
Lisinopril (lye-SIN-o-pril) is a drug of the angiotensin converting enzyme (ACE) inhibitor class that is primarily used in treatment of hypertension, congestive heart failure, heart attacks and also in preventing renal and retinal complications of diabetes. It has been compared with omapatrilat which is of similar function. Historically, lisinopril was the third ACE inhibitor, after captopril and enalapril, and was introduced into therapy in the early 1990s. Lisinopril has a number of properties that distinguish it from other ACE inhibitors: it is hydrophilic, has long half-life and tissue penetration and is not metabolized by the liver. Read more... or Edit at Wikipedia...
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  • miscellaneous
    • Source: synthetic
Names and Synonyms

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

(2S)-1-[(​2S)-6-Ami​no-2-{[(1​S)-1-carb​oxy-3-phe​nylpropyl​]amino}he​xanoyl]-2​-pyrrolid​inecarbox​ylic acid

(2S)-1-[(​2S)-6-Ami​no-2-{[(1​S)-1-carb​oxy-3-phe​nylpropyl​]amino}he​xanoyl]py​rrolidin-​2-carbons​äure

(2S)-1-[(​2S)-6-ami​no-2-{[(1​S)-1-carb​oxy-3-phe​nylpropyl​]amino}he​xanoyl]py​rrolidine​-2-carbox​ylic acid

1-{N~2~-[​(1S)-1-Ca​rboxy-3-p​henylprop​yl]-L-lys​yl}-L-pro​lin

278-488-1 [EINECS/ELINCS]

acide (2S​)-1-[(2S)​-6-amino-​2-{[(1S)-​1-carboxy​-3-phényl​propyl]am​ino}hexan​oyl]pyrro​lidine-2-​carboxyli​que

L-proline​, N~2~-[(​1S)-1-car​boxy-3-ph​enylpropy​l]-L-lysy​l-

N~2~-[(1S​)-1-Carbo​xy-3-phen​ylpropyl]​-L-lysyl-​L-prolina​to

N~2~-[(1S​)-1-Carbo​xy-3-phen​ylpropyl]​-L-lysyl-​L-proline

Renacor

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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

(Details...) Predicted Properties
LogP: ACD/LogP: 1.19
XLogP: -0.90
# of Rule of 5 Violations: 1
ACD/LogD (pH 5.5): ACD/LogD (pH 7.4):
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: 8 #H bond donors: 5
#Freely Rotating Bonds: 13 Polar Surface Area: 79.39 Å2
Index of Refraction: 1.577 Molar Refractivity: 107.48 cm3
Molar Volume: 323.9 cm3 Polarizability: 42.61 10-24cm3
Surface Tension: 60.3 dyne/cm Density: 1.251 g/cm3
Flash Point: 356.9 °C Enthalpy of Vaporization: 102.94 kJ/mol
Boiling Point: 666.4 °C at 760 mmHg Vapour Pressure: 1.14E-18 mmHg at 25°C
MeSH
(Details...) EPI Summary 
            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  -0.94
    Log Kow (Exper. database match) =  -1.22
       Exper. Ref:  Sangster (1993)

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  632.99  (Adapted Stein & Brown method)
    Melting Pt (deg C):  326.37  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.95E-015  (Modified Grain method)
    Subcooled liquid VP: 1.01E-011 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):  13
       log Kow used: -1.22 (expkow database)
       no-melting pt equation used
     Water Sol (Exper. database match) =  9.7e+004 mg/L ( deg C)
        Exper. Ref:  MERCK INDEX (1996)

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1490.2 mg/L
    Wat Sol (Exper. database match) =  97000.00
       Exper. Ref:  MERCK INDEX (1996)

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   1.89E-022  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  1.621E-016 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  -1.22  (exp database)
  Log Kaw used:  -20.112  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  18.892
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.4004
   Biowin2 (Non-Linear Model)     :   0.9971
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.9741  (weeks       )
   Biowin4 (Primary Survey Model) :   4.2622  (hours-days  )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2641
   Biowin6 (MITI Non-Linear Model):   0.0268
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model):  0.0932
 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):  1.35E-009 Pa (1.01E-011 mm Hg)
  Log Koa (Koawin est  ): 18.892
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  2.23E+003 
       Octanol/air (Koa) model:  1.91E+006 
   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 = 168.2442 E-12 cm3/molecule-sec
      Half-Life =     0.064 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     0.763 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    :  7.068E+004
      Log Koc:  4.849 

 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: -1.22 (expkow database)

 Volatilization from Water:
    Henry LC:  1.89E-022 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 6.238E+018  hours   (2.599E+017 days)
    Half-Life from Model Lake : 6.805E+019  hours   (2.835E+018 days)

 Removal In Wastewater Treatment:
    Total removal:               1.85  percent
    Total biodegradation:        0.09  percent
    Total sludge adsorption:     1.75  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       1.06e-009       1.53         1000       
   Water     39              360          1000       
   Soil      61              720          1000       
   Sediment  0.0713          3.24e+003    0          
     Persistence Time: 579 hr
(Details...) SimBioSys LASSO
Descriptors: 0, 0, 3, 3, 0, 0, 0, 8, 0, 0, 0, 0, 17, 5, 4, 0, 6, 6, 3, 1, 0, 0, 0, 0
CategoryTargetPDB CodeLASSO Score
Other EnzymesNA, neuraminidase1a4g0.05
MetalloenzymesACE, angiotensin-converting enzyme1o860.05
Nuclear Hormone ReceptorsPPARg, peroxisome proliferator activated receptor1fm90.03
KinasesSRC, tyrosine kinase SRC2src0.01
Other EnzymesHMGR, hydroxymethylglutaryl-CoA reductase1hw80.01
Other EnzymesHIVPR, HIV protease1hpx0.01
MetalloenzymesPDE5, phosphodiesterase 51xp00.01
Nuclear Hormone ReceptorsMR, mineralocorticoid receptor2aa20.01
Other EnzymesPARP, poly(ADP-ribose) polymerase1efy0.01
Other EnzymesPNP, purine nucleoside phosphorylase1b8o0.00
Other EnzymesAmpC, AmpC beta-lactamase1xgj0.00
Nuclear Hormone ReceptorsER, estrogen receptor; agonist1l2i0.00
Folate EnzymesDHFR, dihydrofolate reductase3dfr0.00
KinasesVEGFr2, vascular endothelial growth factor receptor1vr20.00
Other EnzymesGPB, glycogen phosphorylase1a8i0.00
Nuclear Hormone ReceptorsRXRa, retinoic X receptor R1mvc0.00
Other EnzymesSAHH, S-adenosyl-homocysteine hydrolase1a7a0.00
KinasesFGFr1, fibroblast growth factor receptor kinase1agw0.00
Other EnzymesInhA, enoyl ACP reductase1p440.00
MetalloenzymesCOMT, catechol O-methyltransferase1h1d0.00
Other EnzymesALR2, aldose reductase1ah30.00
KinasesCDK2, cyclindependent kinase 21ckp0.00
Other EnzymesCOX-1, cyclooxygenase-11p4g0.00
KinasesP38 MAP, P38 mitogen activated protein1kv20.00
Serine ProteasesThrombin1ba80.00
Nuclear Hormone ReceptorsAR, androgen receptor1xq20.00
Other EnzymesAChE, acetylcholinesterase1eve0.00
Nuclear Hormone ReceptorsGR, glucocorticoid receptor1m2z0.00
Other EnzymesHIVRT, HIV reverse transcriptase1rt10.00
Folate EnzymesGART, glycinamide ribonucleotide transformylase1c2t0.00
KinasesPDGFrb, platelet derived growth factor receptor kinaseN/A0.00
Nuclear Hormone ReceptorsER, estrogen receptor; antagonist3ert0.00
KinasesHSP90, human heat shock protein 901uy60.00
KinasesTK, thymidine kinase1kim0.00
Serine ProteasesTrypsin1bju0.00
KinasesEGFr, epidermal growth factor receptor1m170.00
Serine ProteasesFXa, factor Xa1f0r0.00
MetalloenzymesADA, adenosine deaminase1stw0.00
Other EnzymesCOX-2, cyclooxygenase-21cx20.00