7-(4-Methoxybenzyl)-6-(3,4,5-trimethoxyphenyl)-5,7-dihydro-4H-[1,2]oxazolo[5,4-e]isoindole

ID: ALA4581544

PubChem CID: 60148281

Max Phase: Preclinical

Molecular Formula: C26H26N2O5

Molecular Weight: 446.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(Cn2cc3c(c2-c2cc(OC)c(OC)c(OC)c2)CCc2cnoc2-3)cc1

Standard InChI:  InChI=1S/C26H26N2O5/c1-29-19-8-5-16(6-9-19)14-28-15-21-20(10-7-17-13-27-33-25(17)21)24(28)18-11-22(30-2)26(32-4)23(12-18)31-3/h5-6,8-9,11-13,15H,7,10,14H2,1-4H3

Standard InChI Key:  JXWDOVBKIROIIP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 33 37  0  0  0  0  0  0  0  0999 V2000
    3.2564  -18.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9617  -18.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6669  -17.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6669  -18.1608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4451  -18.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9261  -17.7518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4451  -17.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2603  -17.3404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9617  -16.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7880  -16.1359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792  -16.0557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532  -16.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6974  -19.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1488  -19.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4007  -20.5699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2007  -20.7405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7485  -20.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4937  -19.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7433  -17.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1519  -17.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9674  -17.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3759  -16.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9673  -15.6307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1459  -15.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7410  -16.3407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542  -21.5173    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9082  -22.1253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5484  -20.2955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8036  -21.0718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8535  -21.1769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1056  -21.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3749  -14.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1921  -14.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  0
  1  2  1  0
  2  4  1  0
  3  9  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  3  2  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  5 13  1  0
  6 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 16 26  1  0
 26 27  1  0
 17 28  1  0
 28 29  1  0
 15 30  1  0
 30 31  1  0
 23 32  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4581544

   7-(4-methoxybenzyl)-6-(3,4,5-trimethoxyphenyl)-5,7-dihydro-4H-isoxazolo[5,4-e]isoindole

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: 446.50

Molecular Weight (Monoisotopic): 446.1842

AlogP: 4.99

#Rotatable Bonds: 7

Polar Surface Area: 67.88

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.04

CX LogP: 4.43

CX LogD: 4.43

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.40

Np Likeness Score: -0.36

References

1. Spanò V, Pennati M, Parrino B, Carbone A, Montalbano A, Cilibrasi V, Zuco V, Lopergolo A, Cominetti D, Diana P, Cirrincione G, Barraja P, Zaffaroni N..  (2016)  Preclinical Activity of New [1,2]Oxazolo[5,4-e]isoindole Derivatives in Diffuse Malignant Peritoneal Mesothelioma.,  59  (15): [PMID:27428868] [10.1021/acs.jmedchem.6b00777]

Source

Source(1):

• Scientific Literature