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ChemSpider ID: |
112213
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Empirical Formula: |
C17H21NO4
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Molecular Weight: |
303.3529
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Nominal Mass: |
303
Da
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Average Mass: |
303.3529
Da
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Monoisotopic Mass: |
303.147058
Da
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Systematic Name: |
ethyl (1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2-carboxylate
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SMILES: |
O=C(O[C@H]1C[C@H]2N[C@@H]([C@H]1C(=O)OCC)CC2)c3ccccc3
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InChI: |
InChI=1/C17H21NO4/c1-2-21-17(20)15-13-9-8-12(18-13)10-14(15)22-16(19)11-6-4-3-5-7-11/h3-7,12-15,18H,2,8-10H2,1H3/t12-,13+,14-,15+/m0/s1
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InChIKey: |
MABVIZVTLRQVOB-LJISPDSOBJ
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users,
Redirected by Users, Redirect Approved by Experts
137220-02-1
[RN]
3-(Benzoyloxy)-8-azabicyclo(3.2.1)octane-2-carboxylic acid ethyl ester
8-Azabicyclo(3.2.1)octane-2-carboxylic acid, 3-(benzoyloxy)-, ethyl ester, (1R-(exo,exo))-
8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-, ethyl ester, (1R,2R,3S,5S)- (9CI)
8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-, ethyl ester, [1R-(exo,exo)]-
Benzoylnorecgonine ethyl ester
Ethyl (1R-(exo,exo))-3-(benzoyloxy)-8-azabiyclo(3.2.1)octane-2-carboxylate
Norcocaethylene
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LogP: |
ACD/LogP:
3.32
XLogP:
2.50
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# of Rule of 5 Violations: |
0
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ACD/LogD (pH 5.5): |
0.34
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ACD/LogD (pH 7.4): |
1.62
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ACD/BCF (pH 5.5): |
1
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ACD/BCF (pH 7.4): |
3.96
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ACD/KOC (pH 5.5): |
1.59
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ACD/KOC (pH 7.4): |
30.76
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#H bond acceptors: |
5
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#H bond donors: |
1
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#Freely Rotating Bonds: |
6
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Polar Surface Area: |
55.84
Å2
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Index of Refraction: |
1.562
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Molar Refractivity: |
80.88
cm3
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Molar Volume: |
249.2
cm3
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Polarizability: |
32.06
10-24cm3
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Surface Tension: |
48.1
dyne/cm
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Density: |
1.21
g/cm3
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Flash Point: |
204.8
°C
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Enthalpy of Vaporization: |
66.81
kJ/mol
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Boiling Point: |
415.1
°C at 760 mmHg
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Vapour Pressure: |
4.23E-07
mmHg at 25°C
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Log Octanol-Water Partition Coef (SRC):
Log Kow (KOWWIN v1.67 estimate) = 2.45
Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
Boiling Pt (deg C): 379.38 (Adapted Stein & Brown method)
Melting Pt (deg C): 111.26 (Mean or Weighted MP)
VP(mm Hg,25 deg C): 3.71E-006 (Modified Grain method)
Subcooled liquid VP: 2.62E-005 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): 967.6
log Kow used: 2.45 (estimated)
no-melting pt equation used
Water Sol Estimate from Fragments:
Wat Sol (v1.01 est) = 910.03 mg/L
ECOSAR Class Program (ECOSAR v0.99h):
Class(es) found:
Aliphatic Amines
Esters
Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
Bond Method : 1.99E-011 atm-m3/mole
Group Method: Incomplete
Henrys LC [VP/WSol estimate using EPI values]: 1.530E-009 atm-m3/mole
Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
Log Kow used: 2.45 (KowWin est)
Log Kaw used: -9.090 (HenryWin est)
Log Koa (KOAWIN v1.10 estimate): 11.540
Log Koa (experimental database): None
Probability of Rapid Biodegradation (BIOWIN v4.10):
Biowin1 (Linear Model) : 1.2334
Biowin2 (Non-Linear Model) : 0.9999
Expert Survey Biodegradation Results:
Biowin3 (Ultimate Survey Model): 2.8557 (weeks )
Biowin4 (Primary Survey Model) : 3.9162 (days )
MITI Biodegradation Probability:
Biowin5 (MITI Linear Model) : 0.7303
Biowin6 (MITI Non-Linear Model): 0.4054
Anaerobic Biodegradation Probability:
Biowin7 (Anaerobic Linear Model): 0.8423
Ready Biodegradability Prediction: YES
Hydrocarbon Biodegradation (BioHCwin v1.01):
Structure incompatible with current estimation method!
Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
Vapor pressure (liquid/subcooled): 0.00349 Pa (2.62E-005 mm Hg)
Log Koa (Koawin est ): 11.540
Kp (particle/gas partition coef. (m3/ug)):
Mackay model : 0.000859
Octanol/air (Koa) model: 0.0851
Fraction sorbed to airborne particulates (phi):
Junge-Pankow model : 0.0301
Mackay model : 0.0643
Octanol/air (Koa) model: 0.872
Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
Hydroxyl Radicals Reaction:
OVERALL OH Rate Constant = 53.2053 E-12 cm3/molecule-sec
Half-Life = 0.201 Days (12-hr day; 1.5E6 OH/cm3)
Half-Life = 2.412 Hrs
Ozone Reaction:
No Ozone Reaction Estimation
Fraction sorbed to airborne particulates (phi): 0.0472 (Junge,Mackay)
Note: the sorbed fraction may be resistant to atmospheric oxidation
Soil Adsorption Coefficient (PCKOCWIN v1.66):
Koc : 2748
Log Koc: 3.439
Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
Total Kb for pH > 8 at 25 deg C : 4.018E-003 L/mol-sec
Kb Half-Life at pH 8: 5.466 years
Kb Half-Life at pH 7: 54.660 years
Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
Log BCF from regression-based method = 1.186 (BCF = 15.35)
log Kow used: 2.45 (estimated)
Volatilization from Water:
Henry LC: 1.99E-011 atm-m3/mole (estimated by Bond SAR Method)
Half-Life from Model River: 5.124E+007 hours (2.135E+006 days)
Half-Life from Model Lake : 5.59E+008 hours (2.329E+007 days)
Removal In Wastewater Treatment:
Total removal: 2.96 percent
Total biodegradation: 0.10 percent
Total sludge adsorption: 2.86 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 0.000374 4.82 1000
Water 19 360 1000
Soil 80.9 720 1000
Sediment 0.122 3.24e+003 0
Persistence Time: 749 hr
Descriptors:
0, 0, 0, 1, 0, 0, 0, 5, 2, 0, 0, 0, 10, 5, 5, 0, 6, 4, 2, 0, 0, 0, 0, 0
| Category | Target | PDB Code | LASSO Score |
| Metalloenzymes | ACE, angiotensin-converting enzyme; | 1o86 | 0.00 |
| Other Enzymes | AChE, acetylcholinesterase; | 1eve | 0.03 |
| Metalloenzymes | ADA, adenosine deaminase; | 1stw | 0.00 |
| Other Enzymes | ALR2, aldose reductase; | 1ah3 | 0.00 |
| Other Enzymes | AmpC, AmpC beta-lactamase; | 1xgj | 0.00 |
| Nuclear Hormone Receptors | AR, androgen receptor; | 1xq2 | 0.00 |
| Kinases | CDK2, cyclindependent kinase 2; | 1ckp | 0.00 |
| Metalloenzymes | COMT, catechol O-methyltransferase; | 1h1d | 0.00 |
| Other Enzymes | cyclooxygenase-2 | 1cx2 | 0.00 |
| Folate Enzymes | DHFR, dihydrofolate reductase; | 3dfr | 0.00 |
| Kinases | EGFr, epidermal growth factor receptor; | 1m17 | 0.00 |
| Nuclear Hormone Receptors | ER, estrogen receptor; agonist | 1l2i | 0.00 |
| Kinases | FGFr1, fibroblast growth factor receptor kinase; | 1agw | 0.00 |
| Serine Proteases | FXa, factor Xa; | 1f0r | 0.00 |
| Folate Enzymes | GART, glycinamide ribonucleotide transformylase; | 1c2t | 0.00 |
| Other Enzymes | GPB, glycogen phosphorylase â; | 1a8i | 0.00 |
| Other Enzymes | HIVPR, HIV protease; | 1hpx | 0.01 |
| Other Enzymes | HIVRT, HIV reverse transcriptase; | 1rt1 | 0.00 |
| Other Enzymes | HMGR, hydroxymethylglutaryl-CoA reductase; | 1hw8 | 0.01 |
| Kinases | HSP90, human heat shock protein 90; | 1uy6 | 0.00 |
| Nuclear Hormone Receptors | MR, mineralocorticoid receptor; | 2aa2 | 0.01 |
| Other Enzymes | NA, neuraminidase; | 1a4g | 0.00 |
| Kinases | P38 MAP, P38 mitogen activated protein; | 1kv2 | 0.00 |
| Other Enzymes | PARP, poly(ADP-ribose) polymerase; | 1efy | 0.01 |
| Metalloenzymes | PDE5, phosphodiesterase 5; | 1xp0 | 0.01 |
| Kinases | PDGFrb, platelet derived growth factor receptor kinase; | | 0.00 |
| Other Enzymes | PNP, purine nucleoside phosphorylase; | 1b8o | 0.00 |
| Nuclear Hormone Receptors | PPARg, peroxisome proliferator activated receptor ç; | 1fm9 | 0.03 |
| Nuclear Hormone Receptors | PR, progesterone receptor; | 1sr7 | 0.00 |
| Nuclear Hormone Receptors | RXRa, retinoic X receptor R; | 1mvc | 0.00 |
| Other Enzymes | SAHH, S-adenosyl-homocysteine hydrolase; | 1a7a | 0.00 |
| Kinases | SRC, tyrosine kinase SRC; | 2src | 0.01 |
| Serine Proteases | Thrombin | 1ba8 | 0.00 |
| Kinases | TK, thymidine kinase; | 1kim | 0.00 |
| Kinases | VEGFr2, vascular endothelial growth factor receptor; | 1vr2 | 0.00 |
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