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ChemSpider ID: |
8252668
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Empirical Formula: |
C29H33FN2O4
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Molecular Weight: |
492.5817
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Nominal Mass: |
492
Da
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Average Mass: |
492.5817
Da
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Monoisotopic Mass: |
492.242436
Da
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Systematic Name: |
ethyl N-[(3R,3aS,4S,4aR,7R,8aR,9aR)-4-[(E)-2-[5-(3-fluorophenyl)-2-pyridyl]vinyl]-3-methyl-1-oxo-3a,4,4a,5,6,7,8,8a,9,9a-decahydro-3H-benzo[f]isobenzofuran-7-yl]carbamate
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SMILES: |
Fc1cccc(c1)c2ccc(nc2)\C=C\[C@H]4[C@H]3[C@@H](C[C@H](NC(=O)OCC)CC3)C[C@H]5C(=O)O[C@@H]([C@@H]45)C
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InChI: |
InChI=1/C29H33FN2O4/c1-3-35-29(34)32-23-10-11-24-20(14-23)15-26-27(17(2)36-28(26)33)25(24)12-9-22-8-7-19(16-31-22)18-5-4-6-21(30)13-18/h4-9,12-13,16-17,20,23-27H,3,10-11,14-15H2,1-2H3,(H,32,34)/b12-9+/t17-,20+,23-,24-,25+,26-,27+/m1/s1
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InChIKey: |
ZBGXUVOIWDMMJE-QHNZEKIYBN
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Description
TRA-SCH 530348 is an oral antiplatelet drug under development by Schering-Plough for the treatment and prevention of atherothrombotic events in patients with Acute Coronary Syndrome, previous Myocardial Infarction, stroke, or existing peripheral arterial disease.
Tags
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SCH 530348
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TRA-SCH 530348
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Links & References
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Samuel Chackalamannil, Yuguang Wang, William J. Greenlee, Zhiyong Hu, Yan Xia, Ho-Sam Ahn, George Boykow, Yunsheng Hsieh, Jairam Palamanda, Jacqueline Agans-Fantuzzi, Stan Kurowski, Michael Graziano, and Madhu Chintala.
Discovery of a Novel, Orally Active Himbacine-Based Thrombin Receptor Antagonist (SCH 530348) with Potent Antiplatelet Activity, ASAP J. Med. Chem., ASAP Article
A potent series of thrombin receptor (PAR-1) antagonists based on the natural product himbacine is described.
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users,
Redirected by Users, Redirect Approved by Experts
carbamic acid, N-[(1R,3aR,4aR,6R,8aR,9S,9aS)-9-[(E)-2-[5-(3-fluorophenyl)-2-pyridinyl]ethenyl]dodecahydro-1-methyl-3-oxonaphtho[2,3-c]furan-6-yl]-, ethyl ester
ethyl [(1R,3aR,4aR,6R,8aR,9S,9aS)-9-{(E)-2-[5-(3-fluorophenyl)pyridin-2-yl]ethenyl}-1-methyl-3-oxododecahydronaphtho[2,3-c]furan-6-yl]carbamate
SCH 530348
TRA-SCH 530348
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LogP: |
ACD/LogP:
4.77
XLogP:
5.50
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# of Rule of 5 Violations: |
0
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ACD/LogD (pH 5.5): |
4.77
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ACD/LogD (pH 7.4): |
4.77
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ACD/BCF (pH 5.5): |
2461.16
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ACD/BCF (pH 7.4): |
2488.41
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ACD/KOC (pH 5.5): |
9281.05
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ACD/KOC (pH 7.4): |
9383.78
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#H bond acceptors: |
6
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#H bond donors: |
1
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#Freely Rotating Bonds: |
6
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Polar Surface Area: |
68.73
Å2
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Index of Refraction: |
1.593
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Molar Refractivity: |
133.71
cm3
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Molar Volume: |
394.1
cm3
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Polarizability: |
53
10-24cm3
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Surface Tension: |
53
dyne/cm
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Density: |
1.24
g/cm3
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Flash Point: |
362.6
°C
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Enthalpy of Vaporization: |
99.25
kJ/mol
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Boiling Point: |
676
°C at 760 mmHg
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Vapour Pressure: |
3.92E-18
mmHg at 25°C
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Log Octanol-Water Partition Coef (SRC):
Log Kow (KOWWIN v1.67 estimate) = 5.21
Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
Boiling Pt (deg C): 613.44 (Adapted Stein & Brown method)
Melting Pt (deg C): 265.59 (Mean or Weighted MP)
VP(mm Hg,25 deg C): 7.55E-014 (Modified Grain method)
Subcooled liquid VP: 3.28E-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): 0.02818
log Kow used: 5.21 (estimated)
no-melting pt equation used
Water Sol Estimate from Fragments:
Wat Sol (v1.01 est) = 0.015778 mg/L
ECOSAR Class Program (ECOSAR v0.99h):
Class(es) found:
Esters
Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
Bond Method : 2.76E-015 atm-m3/mole
Group Method: Incomplete
Henrys LC [VP/WSol estimate using EPI values]: 1.737E-012 atm-m3/mole
Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
Log Kow used: 5.21 (KowWin est)
Log Kaw used: -12.948 (HenryWin est)
Log Koa (KOAWIN v1.10 estimate): 18.158
Log Koa (experimental database): None
Probability of Rapid Biodegradation (BIOWIN v4.10):
Biowin1 (Linear Model) : -0.1978
Biowin2 (Non-Linear Model) : 0.0000
Expert Survey Biodegradation Results:
Biowin3 (Ultimate Survey Model): 1.5830 (recalcitrant)
Biowin4 (Primary Survey Model) : 3.5544 (days-weeks )
MITI Biodegradation Probability:
Biowin5 (MITI Linear Model) : -0.1830
Biowin6 (MITI Non-Linear Model): 0.0000
Anaerobic Biodegradation Probability:
Biowin7 (Anaerobic Linear Model): 0.4969
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): 4.37E-009 Pa (3.28E-011 mm Hg)
Log Koa (Koawin est ): 18.158
Kp (particle/gas partition coef. (m3/ug)):
Mackay model : 686
Octanol/air (Koa) model: 3.53E+005
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 = 111.7624 E-12 cm3/molecule-sec [Cis-isomer]
OVERALL OH Rate Constant = 119.3624 E-12 cm3/molecule-sec [Trans-isomer]
Half-Life = 1.148 Hrs (12-hr day; 1.5E6 OH/cm3) [Cis-isomer]
Half-Life = 1.075 Hrs (12-hr day; 1.5E6 OH/cm3) [Trans-isomer]
Ozone Reaction:
OVERALL Ozone Rate Constant = 6.825000 E-17 cm3/molecule-sec [Cis-]
OVERALL Ozone Rate Constant = 13.650000 E-17 cm3/molecule-sec [Trans-]
Half-Life = 4.030 Hrs (at 7E11 mol/cm3) [Cis-isomer]
Half-Life = 2.015 Hrs (at 7E11 mol/cm3) [Trans-isomer]
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 : 5.391E+006
Log Koc: 6.732
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 = 3.314 (BCF = 2063)
log Kow used: 5.21 (estimated)
Volatilization from Water:
Henry LC: 2.76E-015 atm-m3/mole (estimated by Bond SAR Method)
Half-Life from Model River: 4.708E+011 hours (1.962E+010 days)
Half-Life from Model Lake : 5.136E+012 hours (2.14E+011 days)
Removal In Wastewater Treatment:
Total removal: 83.33 percent
Total biodegradation: 0.71 percent
Total sludge adsorption: 82.62 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 0.000183 1.46 1000
Water 2.54 4.32e+003 1000
Soil 78 8.64e+003 1000
Sediment 19.5 3.89e+004 0
Persistence Time: 9.97e+003 hr
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