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

ID: ALA4740725

PubChem CID: 162645021

Max Phase: Preclinical

Molecular Formula: C22H24N2O5

Molecular Weight: 396.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc2c(n1Cc1cc(OC)ccc1OC)-c1oncc1CCC2

Standard InChI:  InChI=1S/C22H24N2O5/c1-4-28-22(25)18-11-14-6-5-7-15-12-23-29-21(15)20(14)24(18)13-16-10-17(26-2)8-9-19(16)27-3/h8-12H,4-7,13H2,1-3H3

Standard InChI Key:  MMAFNUGHWOLZQA-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
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    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
    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
   10.2334  -10.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8325  -11.0240    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
   10.3002   -9.1245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0248   -8.7300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 20 21  1  0
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 22 23  1  0
 17 24  1  0
 24 25  1  0
 23 26  1  0
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 20 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4740725

   ---

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: 396.44

Molecular Weight (Monoisotopic): 396.1685

AlogP: 3.87

#Rotatable Bonds: 6

Polar Surface Area: 75.72

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.10

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.59

Np Likeness Score: -0.88

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