2-(5-Amino-2-(4-methoxy-2-methylphenethyl)benzo[f][1,7]-naphthyridin-8-yl)ethylphosphonic Acid

ID: ALA3827413

Chembl Id: CHEMBL3827413

PubChem CID: 49838387

Max Phase: Preclinical

Molecular Formula: C24H26N3O4P

Molecular Weight: 451.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CCc2cnc3c(N)nc4cc(CCP(=O)(O)O)ccc4c3c2)c(C)c1

Standard InChI:  InChI=1S/C24H26N3O4P/c1-15-11-19(31-2)7-6-18(15)5-3-17-12-21-20-8-4-16(9-10-32(28,29)30)13-22(20)27-24(25)23(21)26-14-17/h4,6-8,11-14H,3,5,9-10H2,1-2H3,(H2,25,27)(H2,28,29,30)

Standard InChI Key:  QDIIZWCSEUFKCD-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3827413

   2-(5-Amino-2-(4-methoxy-2-methylphenethyl)benzo[f][1,7]naphthyridin-8-yl)ethylphosphonic acid

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: 451.46

Molecular Weight (Monoisotopic): 451.1661

AlogP: 4.19

#Rotatable Bonds: 7

Polar Surface Area: 118.56

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.81

CX Basic pKa: 4.78

CX LogP: 1.65

CX LogD: 1.42

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.28

Np Likeness Score: -0.09

References

1. Cortez A, Li Y, Miller AT, Zhang X, Yue K, Maginnis J, Hampton J, Hall de S, Shapiro M, Nayak B, D'Oro U, Li C, Skibinski D, Mbow ML, Singh M, O'Hagan DT, Cooke MP, Valiante NM, Wu TY..  (2016)  Incorporation of Phosphonate into Benzonaphthyridine Toll-like Receptor 7 Agonists for Adsorption to Aluminum Hydroxide.,  59  (12): [PMID:27270029] [10.1021/acs.jmedchem.6b00489]

Source

Source(1):

• Scientific Literature