Ethanesulfonic acid [4-(acridin-9-ylamino)-3-methoxy-phenyl]-amide

ID: ALA108454

Chembl Id: CHEMBL108454

PubChem CID: 151602

Max Phase: Preclinical

Molecular Formula: C22H21N3O3S

Molecular Weight: 407.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCS(=O)(=O)Nc1ccc(Nc2c3ccccc3nc3ccccc23)c(OC)c1

Standard InChI:  InChI=1S/C22H21N3O3S/c1-3-29(26,27)25-15-12-13-20(21(14-15)28-2)24-22-16-8-4-6-10-18(16)23-19-11-7-5-9-17(19)22/h4-14,25H,3H2,1-2H3,(H,23,24)

Standard InChI Key:  SPMXAUDSAYVFOR-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA108454

   N-[4-(acridin-9-ylamino)-3-methoxyphenyl]ethanesulfonamide

2. Alternative Forms:

   

   ALA108454

   4'-(9-Acridinylamino)-3'-methoxyethanesulfonanilide methanesulfonate

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: 407.50

Molecular Weight (Monoisotopic): 407.1304

AlogP: 4.90

#Rotatable Bonds: 6

Polar Surface Area: 80.32

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.10

CX Basic pKa: 8.45

CX LogP: 3.67

CX LogD: 2.67

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.44

Np Likeness Score: -1.28

References

1. Denny WA, Cain BF, Atwell GJ, Hansch C, Panthananickal A, Leo A..  (1982)  Potential antitumor agents. 36. Quantitative relationships between experimental antitumor activity, toxicity, and structure for the general class of 9-anilinoacridine antitumor agents.,  25  (3): [PMID:7069706] [10.1021/jm00345a015]

2.  (2021)  Compounds for inhibiting ly6k and methods of using same, 

3. Prakash R, Goodlett DW, Varghese S, Andrys J, Gbadamosi FA, Arriaza RH, Patel M, Tiwari PB, Borowski T, Chruszcz M, Shimizu LS, Upadhyay G..  (2023)  Development of fluorophore labeled or biotinylated anticancer small molecule NSC243928.,  79  [PMID:36680947] [10.1016/j.bmc.2023.117171]

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data