ID: ALA146227

Max Phase: Preclinical

Molecular Formula: C9H7NO2

Molecular Weight: 161.16

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=c1[nH]c2ccccc2cc1O

Standard InChI:  InChI=1S/C9H7NO2/c11-8-5-6-3-1-2-4-7(6)10-9(8)12/h1-5,11H,(H,10,12)

Standard InChI Key:  BERPCVULMUPOER-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: 161.16

Molecular Weight (Monoisotopic): 161.0477

AlogP: 1.23

#Rotatable Bonds: 0

Polar Surface Area: 53.09

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 6.84

CX Basic pKa:

CX LogP: 1.35

CX LogD: 0.69

Aromatic Rings: 2

Heavy Atoms: 12

QED Weighted: 0.61

Np Likeness Score: -0.17

References

1. Sit S, Ehrgott FJ, Gao J, Meanwell NA.  (1996)  3-Hydroxy-quinolin-2-ones: Inhibitors of [3H]-glycine binding to the site associated with the NMDA receptor,  6  (5): [10.1016/0960-894X(96)00031-5]

2. Duplantier AJ, Becker SL, Bohanon MJ, Borzilleri KA, Chrunyk BA, Downs JT, Hu LY, El-Kattan A, James LC, Liu S, Lu J, Maklad N, Mansour MN, Mente S, Piotrowski MA, Sakya SM, Sheehan S, Steyn SJ, Strick CA, Williams VA, Zhang L..  (2009)  Discovery, SAR, and pharmacokinetics of a novel 3-hydroxyquinolin-2(1H)-one series of potent D-amino acid oxidase (DAAO) inhibitors.,  52  (11): [PMID:19438227] [10.1021/jm900128w]

3. Suchaud V, Bailly F, Lion C, Tramontano E, Esposito F, Corona A, Christ F, Debyser Z, Cotelle P..  (2012)  Development of a series of 3-hydroxyquinolin-2(1H)-ones as selective inhibitors of HIV-1 reverse transcriptase associated RNase H activity.,  22  (12): [PMID:22607675] [10.1016/j.bmcl.2012.04.096]

4. Hondo T, Warizaya M, Niimi T, Namatame I, Yamaguchi T, Nakanishi K, Hamajima T, Harada K, Sakashita H, Matsumoto Y, Orita M, Takeuchi M..  (2013)  4-Hydroxypyridazin-3(2H)-one derivatives as novel D-amino acid oxidase inhibitors.,  56  (9): [PMID:23566269] [10.1021/jm400095b]

5. Sagong HY, Parhi A, Bauman JD, Patel D, Vijayan RS, Das K, Arnold E, LaVoie EJ..  (2013)  3-Hydroxyquinolin-2(1H)-ones As Inhibitors of Influenza A Endonuclease.,  4  (6): [PMID:24936242] [10.1021/ml4001112]

6. Zimmermann SC, Rais R, Alt J, Burzynski C, Slusher BS, Tsukamoto T..  (2014)  Structure-Metabolism Relationships in the Glucuronidation of d-Amino Acid Oxidase Inhibitors.,  5  (11): [PMID:25408840] [10.1021/ml500335z]

7. Xie D, Lu J, Xie J, Cui J, Li TF, Wang YC, Chen Y, Gong N, Li XY, Fu L, Wang YX..  (2016)  Discovery and analgesic evaluation of 8-chloro-1,4-dihydropyrido[2,3-b]pyrazine-2,3-dione as a novel potent d-amino acid oxidase inhibitor.,  117  [PMID:27089209] [10.1016/j.ejmech.2016.04.017]

8. Szilágyi B, Kovács P, Ferenczy GG, Rácz A, Németh K, Visy J, Szabó P, Ilas J, Balogh GT, Monostory K, Vincze I, Tábi T, Szökő É, Keserű GM..  (2018)  Discovery of isatin and 1H-indazol-3-ol derivatives as d-amino acid oxidase (DAAO) inhibitors.,  26  (8): [PMID:29472125] [10.1016/j.bmc.2018.02.004]

Source

Source(1):

• Scientific Literature