8-Methyl-3-(3-nitro-phenylcarbamoyloxy)-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester

ID: ALA159325

Chembl Id: CHEMBL159325

PubChem CID: 44375616

Max Phase: Preclinical

Molecular Formula: C17H21N3O6

Molecular Weight: 363.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1C2CC[C@H](C[C@@H]1OC(=O)Nc1cccc([N+](=O)[O-])c1)N2C

Standard InChI:  InChI=1S/C17H21N3O6/c1-19-11-6-7-13(19)15(16(21)25-2)14(9-11)26-17(22)18-10-4-3-5-12(8-10)20(23)24/h3-5,8,11,13-15H,6-7,9H2,1-2H3,(H,18,22)/t11-,13?,14+,15?/m1/s1

Standard InChI Key:  FFGDCGSTWMKRRN-CMAYJEJSSA-N

Alternative Forms

1. Parent:

   

   ALA159325

   8-Methyl-3-(3-nitro-phenylcarbamoyloxy)-8-aza-bicyclo[3.2.1]octane-2-carboxylic acid methyl ester

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 363.37

Molecular Weight (Monoisotopic): 363.1430

AlogP: 2.17

#Rotatable Bonds: 4

Polar Surface Area: 111.01

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.58

CX Basic pKa: 8.84

CX LogP: 2.08

CX LogD: 0.62

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.50

Np Likeness Score: -0.22

References

1. Kline RH, Wright J, Eshleman AJ, Fox KM, Eldefrawi ME..  (1991)  Synthesis of 3-carbamoylecgonine methyl ester analogues as inhibitors of cocaine binding and dopamine uptake.,  34  (2): [PMID:1995895] [10.1021/jm00106a035]

2. Carroll FI, Lewin AH, Boja JW, Kuhar MJ..  (1992)  Cocaine receptor: biochemical characterization and structure-activity relationships of cocaine analogues at the dopamine transporter.,  35  (6): [PMID:1552510] [10.1021/jm00084a001]

Source

Source(1):

• Scientific Literature