2-[2-hydroxy-phenyl]-3a,4,9,9a-tetrahydro-4,9-benzeno-benz[f]isoindole-1,3-dione

ID: ALA1094925

PubChem CID: 2831560

Max Phase: Preclinical

Molecular Formula: C24H17NO3

Molecular Weight: 367.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C2C3c4ccccc4C(c4ccccc43)C2C(=O)N1c1ccccc1O

Standard InChI:  InChI=1S/C24H17NO3/c26-18-12-6-5-11-17(18)25-23(27)21-19-13-7-1-2-8-14(13)20(22(21)24(25)28)16-10-4-3-9-15(16)19/h1-12,19-22,26H

Standard InChI Key:  SQUOHYAYYPXXIR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.2352   -0.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1918    0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0713   -0.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5805   -0.8780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2714   -1.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4534   -1.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9454   -1.1014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2573   -0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5045    1.4305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0417    0.7452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2189    0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8577    1.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3255    2.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1467    2.1710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0089   -0.0933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9886    0.7316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7668    1.0059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2679    0.3511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7996   -0.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9995    1.7869    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0707   -1.0974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1137   -1.0402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5072   -0.3265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0833    0.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4762    1.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2920    1.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7134    0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3181   -0.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
 13 14  2  0
 14  9  1  0
  1 10  1  0
  3  2  1  0
 15 16  1  0
  9  2  1  0
  6  7  1  0
  2 16  1  0
  7  8  2  0
  8  3  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 15  1  0
 17 20  2  0
  3  4  2  0
 19 21  2  0
  9 10  2  0
  1  4  1  0
 22 23  1  0
 10 11  1  0
 23 24  2  0
  4  5  1  0
 24 25  1  0
 11 12  2  0
 25 26  2  0
 15  1  1  0
 26 27  1  0
 12 13  1  0
 27 28  2  0
 28 23  1  0
 24 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094925

   17-(2-Hydroxyphenyl)-17-azapentacyclo[6.6.5.0~2,7~.0~9,14~.0~15,19~]nonadeca-2,4,6,9,11,13-hexaene-16,18-dione (non-preferred name)

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: 367.40

Molecular Weight (Monoisotopic): 367.1208

AlogP: 3.79

#Rotatable Bonds: 1

Polar Surface Area: 57.61

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.29

CX Basic pKa: ┄

CX LogP: 3.72

CX LogD: 3.67

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.67

Np Likeness Score: -0.25

References

1. Khalil AM, Berghot MA, Gouda MA..  (2010)  Synthesis and study of some new 1,3-isoindoledione derivatives as potential antibacterial agents.,  45  (4): [PMID:20117862] [10.1016/j.ejmech.2009.12.064]

Source

Source(1):

• Scientific Literature