3-(5-Amino-2-(4-(4,4-difluoro-4-phosphonobutoxy)-2-methylphenethyl)benzo[f][1,7]naphthyridin-8-yl)propanoic Acid

ID: ALA3827669

Chembl Id: CHEMBL3827669

PubChem CID: 49838134

Max Phase: Preclinical

Molecular Formula: C28H30F2N3O6P

Molecular Weight: 573.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(OCCCC(F)(F)P(=O)(O)O)ccc1CCc1cnc2c(N)nc3cc(CCC(=O)O)ccc3c2c1

Standard InChI:  InChI=1S/C28H30F2N3O6P/c1-17-13-21(39-12-2-11-28(29,30)40(36,37)38)8-7-20(17)6-3-19-14-23-22-9-4-18(5-10-25(34)35)15-24(22)33-27(31)26(23)32-16-19/h4,7-9,13-16H,2-3,5-6,10-12H2,1H3,(H2,31,33)(H,34,35)(H2,36,37,38)

Standard InChI Key:  QZDVNZBJWPXLRH-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3827669

   3-(5-Amino-2-(4-(4,4-difluoro-4-phosphonobutoxy)-2-methylphenethyl)benzo[f][1,7]naphthyridin-8-yl)propanoic 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: 573.53

Molecular Weight (Monoisotopic): 573.1840

AlogP: 5.41

#Rotatable Bonds: 12

Polar Surface Area: 155.86

Molecular Species: ACID

HBA: 6

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.64

CX Basic pKa: 4.92

CX LogP: 2.54

CX LogD: -0.81

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.10

Np Likeness Score: -0.19

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