5-Chloro-2,2-dimethyl-2,3-dihydro-benzofuran-7-carboxylic acid (8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl)-amide

ID: ALA2111147

Cas Number: 123482-22-4

PubChem CID: 6918154

Max Phase: Unknown

Molecular Formula: C19H25ClN2O2

Molecular Weight: 348.87

Molecule Type: Small molecule

Names and Identifiers

Synonyms: LY-277359 | LY277359 | ZATOSETRON|LY277359|123482-22-4|901MC95XSB|LY-277359|Zatosetronum|5-chloro-2,2-dimethyl-N-[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]-3H-1-benzofuran-7-carboxamide|7-Benzofurancarboxamide, 5-chloro-2,3-dihydro-2,2-dimethyl-N-(8-methyl-8-azabicyclo(3.2.1)oct-3-yl)-, endo-|Zatosetron [INN:BAN]|Zatosetronum [INN-Latin]|UNII-901MC95XSB|ZATOSETRON [INN]|5-chloro-2,3-dihydro-2,2-dimethyl-N-(8-methyl-8-azabicyclo(3.2.1)oct-3-yl)-7-benzofurancarboxamide|ZATOSETRON [WHO-DD]|SCShow More⌵

Synonyms from Alternative Forms(1): Zatosetron maleate

Canonical SMILES:  CN1[C@@H]2CC[C@H]1C[C@@H](NC(=O)c1cc(Cl)cc3c1OC(C)(C)C3)C2

Standard InChI:  InChI=1S/C19H25ClN2O2/c1-19(2)10-11-6-12(20)7-16(17(11)24-19)18(23)21-13-8-14-4-5-15(9-13)22(14)3/h6-7,13-15H,4-5,8-10H2,1-3H3,(H,21,23)/t13-,14+,15-

Standard InChI Key:  SPKBYQZELVEOLL-QDMKHBRRSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  1  0  0  0  0  0999 V2000
    1.8161   -4.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8161   -5.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4612   -4.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1345   -4.7997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1345   -5.9293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4674   -6.0754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4612   -3.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0987   -4.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7436   -5.3663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0987   -5.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0857   -3.5949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8568   -3.5777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3708   -4.8301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3908   -5.9596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7066   -6.0547    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6997   -3.9237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5943   -4.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2897   -3.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0016   -5.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9478   -3.8596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6363   -4.6674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6363   -5.0436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0802   -4.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3145   -5.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1650   -4.4818    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3982   -4.1595    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  2  6  2  0
  3  7  1  0
  3  8  1  0
  4  9  1  0
  6 10  1  0
  7 11  1  0
  7 12  2  0
  9 13  1  0
  9 14  1  0
 10 15  1  0
 16 11  1  6
 16 17  1  0
 16 18  1  0
 17 19  1  0
 18 20  1  0
 19 21  1  0
 19 22  1  0
 20 23  1  0
 21 24  1  0
  5  9  1  0
  8 10  2  0
 20 21  1  0
 22 23  1  0
  1  2  1  0
  1  3  2  0
  1  4  1  0
 20 25  1  1
 19 26  1  1
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA2111147

   ZATOSETRON MALEATE

2. Parent:

   

   ALA2111147

   ZATOSETRON

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 348.87

Molecular Weight (Monoisotopic): 348.1605

AlogP: 3.41

#Rotatable Bonds: 2

Polar Surface Area: 41.57

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.84

CX Basic pKa: 9.18

CX LogP: 2.78

CX LogD: 1.00

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.89

Np Likeness Score: -0.38

References

1. Schaus JM, Thompson DC, Bloomquist WE, Susemichel AD, Calligaro DO, Cohen ML..  (1998)  Synthesis and structure-activity relationships of potent and orally active 5-HT4 receptor antagonists: indazole and benzimidazolone derivatives.,  41  (11): [PMID:9599243] [10.1021/jm970857f]

2. Robertson DW, Lacefield WB, Bloomquist W, Pfeifer W, Simon RL, Cohen ML..  (1992)  Zatosetron, a potent, selective, and long-acting 5HT3 receptor antagonist: synthesis and structure-activity relationships.,  35  (2): [PMID:1732548] [10.1021/jm00080a016]

3. Robertson DW, Lacefield WB, Bloomquist W, Pfeifer W, Simon RL, Cohen ML..  (1992)  Zatosetron, a potent, selective, and long-acting 5HT3 receptor antagonist: synthesis and structure-activity relationships.,  35  (2): [PMID:1732548] [10.1021/jm00080a016]

4. Molnar L, Keseru GM..  (2002)  A neural network based virtual screening of cytochrome P450 3A4 inhibitors.,  12  (3): [PMID:11814811] [10.1016/s0960-894x(01)00771-5]

5. Wang YH, Li Y, Li YH, Yang SL, Yang L..  (2005)  Modeling K(m) values using electrotopological state: substrates for cytochrome P450 3A4-mediated metabolism.,  15  (18): [PMID:15990295] [10.1016/j.bmcl.2005.06.015]

6. Maksay G, Nemes P, Bíró T..  (2004)  Synthesis of tropeines and allosteric modulation of ionotropic glycine receptors.,  47  (25): [PMID:15566307] [10.1021/jm040814g]

Source

Source(1):

• Scientific Literature