6-chlorobenzo-[d]-isoxazol-3-ol

ID: ALA445990

Cas Number: 61977-29-5

PubChem CID: 2781852

Product Number: C635996, Order Now?

Max Phase: Preclinical

Molecular Formula: C7H4ClNO2

Molecular Weight: 169.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1noc2cc(Cl)ccc12

Standard InChI:  InChI=1S/C7H4ClNO2/c8-4-1-2-5-6(3-4)11-9-7(5)10/h1-3H,(H,9,10)

Standard InChI Key:  SJAPSPJRTQCDNO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 11 12  0  0  0  0  0  0  0  0999 V2000
   -8.7141    3.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4286    3.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1430    3.0643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1431    2.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4286    1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7141    2.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9295    1.9843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4446    2.6518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9294    3.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6745    4.1038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8575    1.8268    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  1  6  1  0
  1  9  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  4 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA445990

   6-chloro-1,2-benzoxazol-3-ol

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

Calculated Properties

Molecular Weight: 169.57

Molecular Weight (Monoisotopic): 168.9931

AlogP: 2.19

#Rotatable Bonds: ┄

Polar Surface Area: 46.26

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.85

CX Basic pKa: ┄

CX LogP: 2.25

CX LogD: 0.78

Aromatic Rings: 2

Heavy Atoms: 11

QED Weighted: 0.66

Np Likeness Score: -1.14

References

1. 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]

2. Sparey T, Abeywickrema P, Almond S, Brandon N, Byrne N, Campbell A, Hutson PH, Jacobson M, Jones B, Munshi S, Pascarella D, Pike A, Prasad GS, Sachs N, Sakatis M, Sardana V, Venkatraman S, Young MB..  (2008)  The discovery of fused pyrrole carboxylic acids as novel, potent D-amino acid oxidase (DAO) inhibitors.,  18  (11): [PMID:18455394] [10.1016/j.bmcl.2008.04.020]

3. Ferraris D, Duvall B, Ko YS, Thomas AG, Rojas C, Majer P, Hashimoto K, Tsukamoto T..  (2008)  Synthesis and biological evaluation of D-amino acid oxidase inhibitors.,  51  (12): [PMID:18507366] [10.1021/jm800200u]

4. Lange JH, Venhorst J, van Dongen MJ, Frankena J, Bassissi F, de Bruin NM, den Besten C, de Beer SB, Oostenbrink C, Markova N, Kruse CG..  (2011)  Biophysical and physicochemical methods differentiate highly ligand-efficient human D-amino acid oxidase inhibitors.,  46  (10): [PMID:21880399] [10.1016/j.ejmech.2011.04.023]

5. PubChem BioAssay data set, 

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. Rais R, Thomas AG, Wozniak K, Wu Y, Jaaro-Peled H, Sawa A, Strick CA, Engle SJ, Brandon NJ, Rojas C, Slusher BS, Tsukamoto T..  (2012)  Pharmacokinetics of oral D-serine in D-amino acid oxidase knockout mice.,  40  (11): [PMID:22837388] [10.1124/dmd.112.046482]

8. 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]

9. 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(2):

• Scientific Literature
• PubChem BioAssays