1,3,5,6,7-pentahydroxyacridin-9(10H)-one

ID: ALA4759231

PubChem CID: 162658845

Max Phase: Preclinical

Molecular Formula: C13H9NO6

Molecular Weight: 275.22

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1c2cc(O)c(O)c(O)c2[nH]c2cc(O)cc(O)c12

Standard InChI:  InChI=1S/C13H9NO6/c15-4-1-6-9(7(16)2-4)11(18)5-3-8(17)12(19)13(20)10(5)14-6/h1-3,15-17,19-20H,(H,14,18)

Standard InChI Key:  OABKNXPPQWGEBD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   10.0195   -8.7579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0183   -9.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7264   -9.9864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7246   -8.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4332   -8.7543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4321   -9.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1383   -9.9840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1406   -8.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1406   -7.5256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8513   -8.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8496   -9.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5552   -9.9815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2630   -9.5738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2607   -8.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5545   -8.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5526   -7.5320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9711   -9.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7281  -10.8036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3103   -9.9855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3117   -8.3495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5  8  1  0
  6  7  1  0
  7 11  1  0
 10  8  1  0
  8  9  2  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
 15 16  1  0
 13 17  1  0
  3 18  1  0
  2 19  1  0
  1 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4759231

   ---

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: 275.22

Molecular Weight (Monoisotopic): 275.0430

AlogP: 1.21

#Rotatable Bonds: ┄

Polar Surface Area: 134.01

Molecular Species: NEUTRAL

HBA: 6

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.46

CX Basic pKa: ┄

CX LogP: 3.33

CX LogD: 3.03

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.27

Np Likeness Score: 1.32

References

1. Rząd K,Paluszkiewicz E,Gabriel I.  (2021)  A new 1-nitro-9-aminoacridine derivative targeting yeast topoisomerase II able to overcome fluconazole-resistance.,  35  [PMID:33486051] [10.1016/j.bmcl.2021.127815]

Source

Source(1):

• Scientific Literature