Ethyl 9-(2-Methoxybenzyl)-4,5,6,9-tetrahydropyrrolo[2',3':3,4]-cyclohepta[1,2-d][1,2]oxazole-8-carboxylate

ID: ALA4762893

PubChem CID: 155811364

Max Phase: Preclinical

Molecular Formula: C21H22N2O4

Molecular Weight: 366.42

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc2c(n1Cc1ccccc1OC)-c1oncc1CCC2

Standard InChI:  InChI=1S/C21H22N2O4/c1-3-26-21(24)17-11-14-8-6-9-15-12-22-27-20(15)19(14)23(17)13-16-7-4-5-10-18(16)25-2/h4-5,7,10-12H,3,6,8-9,13H2,1-2H3

Standard InChI Key:  RCNUWMKOEMRRAZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    4.9930   -9.1249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6570   -9.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1413  -11.2447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7374  -11.8516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5374  -11.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2576  -10.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9714  -10.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7689  -10.3279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9952  -11.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7887  -11.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0528  -10.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4226   -9.8777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4432   -9.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8436  -10.1248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0352   -9.3224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4427  -10.6920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8260   -9.0872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0177   -8.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1678   -8.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8717   -9.0887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5963   -8.6942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6170   -7.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9130   -7.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1885   -7.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4845   -7.4035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5052   -6.5787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 20 25  2  0
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 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4762893

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 366.42

Molecular Weight (Monoisotopic): 366.1580

AlogP: 3.87

#Rotatable Bonds: 5

Polar Surface Area: 66.49

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.10

CX LogP: 3.98

CX LogD: 3.98

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: -0.98

References

1. Spanò V,Rocca R,Barreca M,Giallombardo D,Montalbano A,Carbone A,Raimondi MV,Gaudio E,Bortolozzi R,Bai R,Tassone P,Alcaro S,Hamel E,Viola G,Bertoni F,Barraja P.  (2020)  Pyrrolo[2',3':3,4]cyclohepta[1,2-d][1,2]oxazoles, a New Class of Antimitotic Agents Active against Multiple Malignant Cell Types.,  63  (20.0): [PMID:32986419] [10.1021/acs.jmedchem.0c01315]

Source

Source(1):

• Scientific Literature