InChI=1/C23H32N2O5/c1-3-30-23(29)18(13-12-16-8-5-4-6-9-16)24-15(2)21(26)25-19-11-7-10-17(19)14-20(25)22(27)28/h4-6,8-9,15,17-20,24H,3,7,10-14H2,1-2H3,(H,27,28)/t15-,17-,18-,19-,20-/m0/s1

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Inherent Properties, Identifiers and References

ChemSpider ID:	4514937
Empirical Formula:	C₂₃H₃₂N₂O₅
Molecular Weight:	416.5106
Nominal Mass:	416 Da
Average Mass:	416.5106 Da
Monoisotopic Mass:	416.231122 Da

Systematic Name:

(2S,3aS,6aS)-1-[(2S)-2-[[(1S)-1-ethoxycarbonyl-3-phenyl-propyl]amino]propanoyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[d]pyrrole-2-carboxylic acid

SMILES:

O=C(OCC)[C@@H](N[C@H](C(=O)N1[C@H](C(=O)O)C[C@@H]2CCC[C@H]12)C)CCc3ccccc3

InChI:

InChI=1/C23H32N2O5/c1-3-30-23(29)18(13-12-16-8-5-4-6-9-16)24-15(2)21(26)25-19-11-7-10-17(19)14-20(25)22(27)28/h4-6,8-9,15,17-20,24H,3,7,10-14H2,1-2H3,(H,27,28)/t15-,17-,18-,19-,20-/m0/s1

InChIKey:

HDACQVRGBOVJII-JBDAPHQKBG

Std. InChI:

InChI=1S/C23H32N2O5/c1-3-30-23(29)18(13-12-16-8-5-4-6-9-16)24-15(2)21(26)25-19-11-7-10-17(19)14-20(25)22(27)28/h4-6,8-9,15,17-20,24H,3,7,10-14H2,1-2H3,(H,27,28)/t15-,17-,18-,19-,20-/m0/s1

Std. InChIKey:

HDACQVRGBOVJII-JBDAPHQKSA-N

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Wikipedia Article(s)

Ramipril (marketed as Ramipro by Westfield Pharma in the Philippines, marketed by Sanofi-Aventis as Tritace and by King Pharmaceuticals as Altace in the United States) is an angiotensin-converting enzyme (ACE) inhibitor, used to treat hypertension and congestive heart failure. ACE inhibitors lower the production of angiotensin II, therefore relaxing arterial muscles while at the same time enlarging the arteries, allowing the heart to pump blood more easily, and increasing blood flow due to more blood being pumped into and through larger passageways. Ramipril is a prodrug and is converted to the active metabolite ramiprilat by liver esterase enzymes. Ramiprilat is mostly excreted by the kidneys. The half-life of ramiprilat is variable (3-16 hours), and is prolonged by heart and liver failure, as well as kidney failure. It is marketed by King Pharmaceuticals under the brand name Altace. The compound was protected by the (was scheduled to expire on 29^th Oct, 2008) assigned to Aventis. On September 11, 2007 in an appeal by Lupin Pharmaceuticals the United States Court of Appeals for the Federal Circuit reversed a district court trial verdict, finding that Aventis's patent on Altace was invalid for obviousness - opening the gate of this medicine to generic manufacturers. Ramipril is marketed in India under the brand names of Cardace, Zigpril and Zorem. Read more... or Edit at Wikipedia...

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miscellaneous

Source: synthetic; HOE-498

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Names and Synonyms

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

(2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino}propanoyl]octahydrocyclopenta[b]pyrrol-2-carbonsäure

(2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid

(2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid (non-preferred name)

(2S,3aS,6aS)-1-[(2S)-2-{[(2S)-1-Ethoxy-1-oxo-4-phenyl-2-butanyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid (non-preferred name)

(2S,3aS,6aS)-1-[(2S)-2-{[(2S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid (non-preferred name)

(2S,3aS,6aS)-1-[(S)-N-[(S)-1-Carboxy-3-phenylpropyl]alanyl]octahydrocyclopenta[b]pyrrole-2-carboxylic Acid 1-Ethyl Ester

(2S,3aS,6aS)-1-{2-[(1-ethoxy-1-oxo-4-phenylbutan-2-yl)amino]propanoyl}octahydrocyclopenta[b]pyrrole-2-carboxylic acid (non-preferred name)

[2S-[1[R*(R*)],2a,3ab,6ab]]-1-[2-[[1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]octahydrocyclopenta[b]pyrrole-2-carboxylic Acid

acide (2S,3aS,6aS)-1-[(2S)-2-{[(1S)-1-(éthoxycarbonyl)-3-phénylpropyl]amino}propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylique

N-(1S-Carboethoxy-3-phenylpropyl)-S-alanyl-cis,endo-2-azabicyclo[3.3.0]octane-3S-carboxylic Acid

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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

ACD/Labs Predicted Properties

ACD/LogP:	3.41	# of Rule of 5 Violations:	0
ACD/LogD (pH 5.5):	1.24	ACD/LogD (pH 7.4):
ACD/BCF (pH 5.5):	1.57	ACD/BCF (pH 7.4):	1
ACD/KOC (pH 5.5):	11.66	ACD/KOC (pH 7.4):	1
#H bond acceptors:	7	#H bond donors:	2
#Freely Rotating Bonds:	10	Polar Surface Area:	76.15 Å²
Index of Refraction:	1.555	Molar Refractivity:	111.41 cm³
Molar Volume:	346.8 cm³	Polarizability:	44.16 10^-24cm³
Surface Tension:	50.1 dyne/cm	Density:	1.2 g/cm³
Flash Point:	326.4 °C	Enthalpy of Vaporization:	96.09 kJ/mol
Boiling Point:	616.2 °C at 760 mmHg	Vapour Pressure:	4.86E-16 mmHg at 25°C

MeSH

EPI Summary

            
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  3.32

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  579.38  (Adapted Stein & Brown method)
    Melting Pt (deg C):  318.54  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  3.8E-011  (Modified Grain method)
    MP  (exp database):  109 deg C
    Subcooled liquid VP: 2.54E-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):  3.551
       log Kow used: 3.32 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1106.5 mg/L

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

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   3.44E-016  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  5.865E-012 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  3.32  (KowWin est)
  Log Kaw used:  -13.852  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  17.172
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   1.3429
   Biowin2 (Non-Linear Model)     :   0.9997
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.7009  (weeks-months)
   Biowin4 (Primary Survey Model) :   4.0464  (days        )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :   0.2577
   Biowin6 (MITI Non-Linear Model):   0.0270
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.3772
 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):  3.39E-008 Pa (2.54E-010 mm Hg)
  Log Koa (Koawin est  ): 17.172
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  88.6 
       Octanol/air (Koa) model:  3.65E+004 
   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 = 123.2510 E-12 cm3/molecule-sec
      Half-Life =     0.087 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     1.041 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    :  1674
      Log Koc:  3.224 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
  Total Kb for pH > 8 at 25 deg C :  1.747E-003  L/mol-sec
  Kb Half-Life at pH 8:      12.575  years  
  Kb Half-Life at pH 7:     125.745  years  

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 0.500 (BCF = 3.162)
       log Kow used: 3.32 (estimated)

 Volatilization from Water:
    Henry LC:  3.44E-016 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 3.474E+012  hours   (1.447E+011 days)
    Half-Life from Model Lake : 3.789E+013  hours   (1.579E+012 days)

 Removal In Wastewater Treatment:
    Total removal:               9.54  percent
    Total biodegradation:        0.16  percent
    Total sludge adsorption:     9.39  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       7.88e-008       2.08         1000       
   Water     11.9            900          1000       
   Soil      87.5            1.8e+003     1000       
   Sediment  0.566           8.1e+003     0          
     Persistence Time: 1.82e+003 hr

SimBioSys LASSO

Descriptors: 0, 0, 0, 2, 0, 0, 0, 7, 1, 0, 0, 0, 21, 5, 4, 0, 6, 6, 3, 1, 0, 0, 0, 0

Category	Target	PDB Code	LASSO Score
Metalloenzymes	ACE, angiotensin-converting enzyme	1o86	0.03
Nuclear Hormone Receptors	PPARg, peroxisome proliferator activated receptor	1fm9	0.03
Other Enzymes	AChE, acetylcholinesterase	1eve	0.01
Kinases	SRC, tyrosine kinase SRC	2src	0.01
Other Enzymes	HMGR, hydroxymethylglutaryl-CoA reductase	1hw8	0.01
Other Enzymes	HIVPR, HIV protease	1hpx	0.01
Metalloenzymes	PDE5, phosphodiesterase 5	1xp0	0.01
Nuclear Hormone Receptors	MR, mineralocorticoid receptor	2aa2	0.01
Serine Proteases	Thrombin	1ba8	0.01
Other Enzymes	PARP, poly(ADP-ribose) polymerase	1efy	0.01
Other Enzymes	PNP, purine nucleoside phosphorylase	1b8o	0.00
Other Enzymes	AmpC, AmpC beta-lactamase	1xgj	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; agonist	1l2i	0.00
Folate Enzymes	DHFR, dihydrofolate reductase	3dfr	0.00
Other Enzymes	HIVRT, HIV reverse transcriptase	1rt1	0.00
Kinases	VEGFr2, vascular endothelial growth factor receptor	1vr2	0.00
Other Enzymes	GPB, glycogen phosphorylase	1a8i	0.00
Other Enzymes	NA, neuraminidase	1a4g	0.00
Other Enzymes	SAHH, S-adenosyl-homocysteine hydrolase	1a7a	0.00
Kinases	FGFr1, fibroblast growth factor receptor kinase	1agw	0.00
Nuclear Hormone Receptors	RXRa, retinoic X receptor R	1mvc	0.00
Other Enzymes	InhA, enoyl ACP reductase	1p44	0.00
Metalloenzymes	COMT, catechol O-methyltransferase	1h1d	0.00
Other Enzymes	ALR2, aldose reductase	1ah3	0.00
Kinases	CDK2, cyclindependent kinase 2	1ckp	0.00
Other Enzymes	COX-1, cyclooxygenase-1	1p4g	0.00
Kinases	P38 MAP, P38 mitogen activated protein	1kv2	0.00
Nuclear Hormone Receptors	AR, androgen receptor	1xq2	0.00
Nuclear Hormone Receptors	GR, glucocorticoid receptor	1m2z	0.00
Nuclear Hormone Receptors	ER, estrogen receptor; antagonist	3ert	0.00
Folate Enzymes	GART, glycinamide ribonucleotide transformylase	1c2t	0.00
Kinases	PDGFrb, platelet derived growth factor receptor kinase	N/A	0.00
Kinases	HSP90, human heat shock protein 90	1uy6	0.00
Serine Proteases	Trypsin	1bju	0.00
Kinases	TK, thymidine kinase	1kim	0.00
Kinases	EGFr, epidermal growth factor receptor	1m17	0.00
Serine Proteases	FXa, factor Xa	1f0r	0.00
Metalloenzymes	ADA, adenosine deaminase	1stw	0.00
Other Enzymes	COX-2, cyclooxygenase-2	1cx2	0.00