ID: ALA3359091

Max Phase: Preclinical

Molecular Formula: C26H22FN3O6

Molecular Weight: 491.48

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cccc(CNC(=O)c2nc3ccc(F)c(OCCc4ccc(C(=O)O)cc4)c3c(=O)[nH]2)c1

Standard InChI:  InChI=1S/C26H22FN3O6/c1-35-18-4-2-3-16(13-18)14-28-25(32)23-29-20-10-9-19(27)22(21(20)24(31)30-23)36-12-11-15-5-7-17(8-6-15)26(33)34/h2-10,13H,11-12,14H2,1H3,(H,28,32)(H,33,34)(H,29,30,31)

Standard InChI Key:  YNHGVYGMFAREOF-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: 491.48

Molecular Weight (Monoisotopic): 491.1493

AlogP: 3.32

#Rotatable Bonds: 9

Polar Surface Area: 130.61

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.20

CX Basic pKa: 0.89

CX LogP: 3.37

CX LogD: 0.09

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.33

Np Likeness Score: -0.94

References

1. Nara H, Sato K, Naito T, Mototani H, Oki H, Yamamoto Y, Kuno H, Santou T, Kanzaki N, Terauchi J, Uchikawa O, Kori M..  (2014)  Discovery of novel, highly potent, and selective quinazoline-2-carboxamide-based matrix metalloproteinase (MMP)-13 inhibitors without a zinc binding group using a structure-based design approach.,  57  (21): [PMID:25264600] [10.1021/jm500981k]

2. Nara H, Sato K, Kaieda A, Oki H, Kuno H, Santou T, Kanzaki N, Terauchi J, Uchikawa O, Kori M..  (2016)  Design, synthesis, and biological activity of novel, potent, and highly selective fused pyrimidine-2-carboxamide-4-one-based matrix metalloproteinase (MMP)-13 zinc-binding inhibitors.,  24  (23): [PMID:27825552] [10.1016/j.bmc.2016.09.009]

3. Laleu B, Akao Y, Ochida A, Duffy S, Lucantoni L, Shackleford DM, Chen G, Katneni K, Chiu FCK, White KL, Chen X, Sturm A, Dechering KJ, Crespo B, Sanz LM, Wang B, Wittlin S, Charman SA, Avery VM, Cho N, Kamaura M..  (2021)  Discovery and Structure-Activity Relationships of Quinazolinone-2-carboxamide Derivatives as Novel Orally Efficacious Antimalarials.,  64  (17.0): [PMID:34437804] [10.1021/acs.jmedchem.1c00441]

Source

Source(1):

• Scientific Literature