8-chloro-9-oxo-9,10-dihydroacridine-4-carboxylic acid

ID: ALA5184333

PubChem CID: 13352682

Max Phase: Preclinical

Molecular Formula: C14H8ClNO3

Molecular Weight: 273.68

Names and Identifiers

Canonical SMILES:  O=C(O)c1cccc2c(=O)c3c(Cl)cccc3[nH]c12

Standard InChI:  InChI=1S/C14H8ClNO3/c15-9-5-2-6-10-11(9)13(17)7-3-1-4-8(14(18)19)12(7)16-10/h1-6H,(H,16,17)(H,18,19)

Standard InChI Key:  BMGULOBUFVMMEN-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
   -2.1441    0.6193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4295    1.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7176    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7176   -0.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4277   -0.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1441   -0.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0030   -0.6180    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0030    1.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7116    0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0030    1.8574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4295    1.8567    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.7116   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4243    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1392    0.6181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1411   -0.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294   -0.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4294   -1.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1441   -1.8574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7147   -1.8574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  1  6  1  0
  6  5  2  0
  4  7  1  0
  3  8  1  0
  8  9  1  0
  8 10  2  0
  2 11  1  0
  7 12  1  0
 12  9  2  0
  9 13  1  0
 14 13  2  0
 15 14  1  0
 16 15  2  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5184333

   8-chloro-9-oxo-10H-acridine-4-carboxylic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 273.68

Molecular Weight (Monoisotopic): 273.0193

AlogP: 3.03

#Rotatable Bonds: 1

Polar Surface Area: 70.16

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.61

CX Basic pKa: ┄

CX LogP: 4.46

CX LogD: 1.12

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.67

Np Likeness Score: -0.11

References

1. Shishodia S, Nuñez R, Strohmier BP, Bursch KL, Goetz CJ, Olp MD, Jensen DR, Fenske TG, Ordonez-Rubiano SC, Blau ME, Roach MK, Peterson FC, Volkman BF, Dykhuizen EC, Smith BC..  (2022)  Selective and Cell-Active PBRM1 Bromodomain Inhibitors Discovered through NMR Fragment Screening.,  65  (20.0): [PMID:36227159] [10.1021/acs.jmedchem.2c00864]

Source

Source(1):

• Scientific Literature