ID: ALA3337869

Max Phase: Preclinical

Molecular Formula: C17H15N3O3

Molecular Weight: 309.33

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cccc(CNC(=O)c2nc3ccccc3c(=O)[nH]2)c1

Standard InChI:  InChI=1S/C17H15N3O3/c1-23-12-6-4-5-11(9-12)10-18-17(22)15-19-14-8-3-2-7-13(14)16(21)20-15/h2-9H,10H2,1H3,(H,18,22)(H,19,20,21)

Standard InChI Key:  AARSEFXVCWMMKV-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: 309.33

Molecular Weight (Monoisotopic): 309.1113

AlogP: 1.86

#Rotatable Bonds: 4

Polar Surface Area: 84.08

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 7.79

CX Basic pKa: 1.48

CX LogP: 1.72

CX LogD: 1.59

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.77

Np Likeness Score: -1.24

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)  Thieno[2,3-d]pyrimidine-2-carboxamides bearing a carboxybenzene group at 5-position: highly potent, selective, and orally available MMP-13 inhibitors interacting with the S1″ binding site.,  22  (19): [PMID:25192810] [10.1016/j.bmc.2014.07.025]

2. 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]

3. 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]

4. Nara H, Kaieda A, Sato K, Naito T, Mototani H, Oki H, Yamamoto Y, Kuno H, Santou T, Kanzaki N, Terauchi J, Uchikawa O, Kori M..  (2017)  Discovery of Novel, Highly Potent, and Selective Matrix Metalloproteinase (MMP)-13 Inhibitors with a 1,2,4-Triazol-3-yl Moiety as a Zinc Binding Group Using a Structure-Based Design Approach.,  60  (2): [PMID:27966948] [10.1021/acs.jmedchem.6b01007]

Source

Source(1):

• Scientific Literature