ID: ALA97380

Max Phase: Preclinical

Molecular Formula: C28H23NO5

Molecular Weight: 453.49

Molecule Type: Small molecule

Representations

Canonical SMILES:  N#Cc1cc(-c2ccoc2)c2ccc(OCc3cccc(C4(O)CC5COC(C4)O5)c3)cc2c1

Standard InChI:  InChI=1S/C28H23NO5/c29-14-19-8-21-11-23(4-5-25(21)26(10-19)20-6-7-31-16-20)32-15-18-2-1-3-22(9-18)28(30)12-24-17-33-27(13-28)34-24/h1-11,16,24,27,30H,12-13,15,17H2

Standard InChI Key:  CHLJRXIFRPILDX-UHFFFAOYSA-N

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

Properties

Molecular Weight: 453.49

Molecular Weight (Monoisotopic): 453.1576

AlogP: 5.27

#Rotatable Bonds: 5

Polar Surface Area: 84.85

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.80

CX Basic pKa:

CX LogP: 4.67

CX LogD: 4.67

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.44

Np Likeness Score: 0.23

References

1. Hamel P, Riendeau D, Brideau C, Chan CC, Desmarais S, Delorme D, Dubé D, Ducharme Y, Ethier D, Grimm E, Falgueyret JP, Guay J, Jones TR, Kwong E, McAuliffe M, McFarlane CS, Piechuta H, Roumi M, Tagari P, Young RN, Girard Y..  (1997)  Substituted (pyridylmethoxy)naphthalenes as potent and orally active 5-lipoxygenase inhibitors; synthesis, biological profile, and pharmacokinetics of L-739,010.,  40  (18): [PMID:9288168] [10.1021/jm970046b]

2. Delorme D, Ducharme Y, Brideau C, Chan CC, Chauret N, Desmarais S, Dubé D, Falgueyret JP, Fortin R, Guay J, Hamel P, Jones TR, Lépine C, Li C, McAuliffe M, McFarlane CS, Nicoll-Griffith DA, Riendeau D, Yergey JA, Girard Y..  (1996)  Dioxabicyclooctanyl naphthalenenitriles as nonredox 5-lipoxygenase inhibitors: structure-activity relationship study directed toward the improvement of metabolic stability.,  39  (20): [PMID:8831761] [10.1021/jm960301c]

3. Wu YJ, Meanwell NA..  (2021)  Geminal Diheteroatomic Motifs: Some Applications of Acetals, Ketals, and Their Sulfur and Nitrogen Homologues in Medicinal Chemistry and Drug Design.,  64  (14.0): [PMID:34213340] [10.1021/acs.jmedchem.1c00790]

Source

Source(1):

• Scientific Literature