3-((3-(2-(2-(Aminomethyl)-5-chlorobenzylamino)-2-oxoethyl)-4-methyl-2-oxo-5,6-dihydropyridin-1(2H)-ylamino)methyl)benzoic acid

ID: ALA4443619

Chembl Id: CHEMBL4443619

PubChem CID: 155516479

Max Phase: Preclinical

Molecular Formula: C24H27ClN4O4

Molecular Weight: 470.96

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC1=C(CC(=O)NCc2cc(Cl)ccc2CN)C(=O)N(NCc2cccc(C(=O)O)c2)CC1

Standard InChI:  InChI=1S/C24H27ClN4O4/c1-15-7-8-29(28-13-16-3-2-4-17(9-16)24(32)33)23(31)21(15)11-22(30)27-14-19-10-20(25)6-5-18(19)12-26/h2-6,9-10,28H,7-8,11-14,26H2,1H3,(H,27,30)(H,32,33)

Standard InChI Key:  YWILLTRBAXHNHO-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA4443619

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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: 470.96

Molecular Weight (Monoisotopic): 470.1721

AlogP: 2.76

#Rotatable Bonds: 9

Polar Surface Area: 124.76

Molecular Species: ZWITTERION

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.13

CX Basic pKa: 8.85

CX LogP: -0.46

CX LogD: -0.47

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.45

Np Likeness Score: -0.66

References

1. Andersson V, Bergström F, Brånalt J, Grönberg G, Gustafsson D, Karlsson S, Polla M, Bergman J, Kihlberg J..  (2016)  Macrocyclic Prodrugs of a Selective Nonpeptidic Direct Thrombin Inhibitor Display High Permeability, Efficient Bioconversion but Low Bioavailability.,  59  (14): [PMID:27347787] [10.1021/acs.jmedchem.5b01871]

Source

Source(1):

• Scientific Literature