5-(5-Hydroxybenzofuran-2-yl)-7-iodoquinolin-8-ol hydrochloride

ID: ALA3735824

PubChem CID: 127035974

Max Phase: Preclinical

Molecular Formula: C17H11ClINO3

Molecular Weight: 403.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.Oc1ccc2oc(-c3cc(I)c(O)c4ncccc34)cc2c1

Standard InChI:  InChI=1S/C17H10INO3.ClH/c18-13-8-12(11-2-1-5-19-16(11)17(13)21)15-7-9-6-10(20)3-4-14(9)22-15;/h1-8,20-21H;1H

Standard InChI Key:  CRLYYEDZORVTOO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    6.3926   -3.0839    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0829   -7.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6924   -8.9068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533   -5.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5584   -5.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5880   -7.8900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4929   -3.8389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    2.6973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0865   -3.8662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6321    1.3486    0.0000 I   0  0  0  0  0  0  0  0  0  0  0  0
    2.8337   -6.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1926   -6.5861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 21 11  1  0
 20  3  2  0
  8 12  1  0
 21 15  1  0
 17  7  1  0
 17 11  1  0
 14  6  1  0
 22 21  2  0
 12 10  2  0
 11 14  2  0
  3 13  1  0
  9 23  1  0
 20 10  1  0
  6  7  1  0
 15  8  2  0
 13  4  2  0
  6 19  2  0
  2  9  2  0
  2  5  1  0
 12 16  1  0
  7 23  2  0
  4 22  1  0
  8 18  1  0
 19  2  1  0
 22 10  1  0
M  END

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: 403.18

Molecular Weight (Monoisotopic): 402.9705

AlogP: 4.66

#Rotatable Bonds: 1

Polar Surface Area: 66.49

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.34

CX Basic pKa: 3.77

CX LogP: 4.18

CX LogD: 3.84

Aromatic Rings: 4

Heavy Atoms: 22

QED Weighted: 0.45

Np Likeness Score: 0.18

References

1. Wang Z, Wang Y, Wang B, Li W, Huang L, Li X..  (2015)  Design, Synthesis, and Evaluation of Orally Available Clioquinol-Moracin M Hybrids as Multitarget-Directed Ligands for Cognitive Improvement in a Rat Model of Neurodegeneration in Alzheimer's Disease.,  58  (21): [PMID:26473791] [10.1021/acs.jmedchem.5b01222]

Source

Source(1):

• Scientific Literature