rac-7-(phenyl(pyridin-2-ylamino)methyl)quinolin-8-ol

ID: ALA1688558

Chembl Id: CHEMBL1688558

Cas Number: 304685-32-3

PubChem CID: 256756

Max Phase: Preclinical

Molecular Formula: C21H17N3O

Molecular Weight: 327.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: NSC-84094 | NSC84094|304685-32-3|CHEMBL1688558|7-[phenyl(pyridin-2-ylamino)methyl]quinolin-8-ol|7-{phenyl[(pyridin-2-yl)amino]methyl}quinolin-8-ol|NSC-84094|7-(phenyl(pyridin-2-ylamino)methyl)quinolin-8-ol|Enamine_000429|Oprea1_081069|Oprea1_364130|7-[phenyl-(pyridin-2-ylamino)methyl]quinolin-8-ol|SCHEMBL5090192|HMS1395D11|BDBM50339142|NSC 84094|AKOS000808675|AKOS016195443|NCGC00187803-01|NCGC00187803-02|NCI60_041847|7-(phenyl(2-pyridinylamino)methyl)-8-quinolinol|EN300-18210086|rac-7-(phenyl(pyShow More⌵

Canonical SMILES:  Oc1c(C(Nc2ccccn2)c2ccccc2)ccc2cccnc12

Standard InChI:  InChI=1S/C21H17N3O/c25-21-17(12-11-16-9-6-14-23-20(16)21)19(15-7-2-1-3-8-15)24-18-10-4-5-13-22-18/h1-14,19,25H,(H,22,24)

Standard InChI Key:  WHPVVFZPXKODBB-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1688558

   7-[Phenyl(pyridin-2-ylamino)methyl]quinolin-8-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: 327.39

Molecular Weight (Monoisotopic): 327.1372

AlogP: 4.54

#Rotatable Bonds: 4

Polar Surface Area: 58.04

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.53

CX Basic pKa: 6.51

CX LogP: 4.19

CX LogD: 4.10

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.58

Np Likeness Score: -1.00

References

1. Roxas-Duncan V, Enyedy I, Montgomery VA, Eccard VS, Carrington MA, Lai H, Gul N, Yang DC, Smith LA..  (2009)  Identification and biochemical characterization of small-molecule inhibitors of Clostridium botulinum neurotoxin serotype A.,  53  (8): [PMID:19528275] [10.1128/aac.00141-09]

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. Caglič D, Krutein MC, Bompiani KM, Barlow DJ, Benoni G, Pelletier JC, Reitz AB, Lairson LL, Houseknecht KL, Smith GR, Dickerson TJ..  (2014)  Identification of clinically viable quinolinol inhibitors of botulinum neurotoxin A light chain.,  57  (3): [PMID:24387280] [10.1021/jm4012164]

5. Harrell WA, Vieira RC, Ensel SM, Montgomery V, Guernieri R, Eccard VS, Campbell Y, Roxas-Duncan V, Cardellina JH, Webb RP, Smith LA..  (2017)  A matrix-focused structure-activity and binding site flexibility study of quinolinol inhibitors of botulinum neurotoxin serotype A.,  27  (3): [PMID:28043798] [10.1016/j.bmcl.2016.11.019]

6. Bremer PT, Adler M, Phung CH, Singh AK, Janda KD..  (2017)  Newly Designed Quinolinol Inhibitors Mitigate the Effects of Botulinum Neurotoxin A in Enzymatic, Cell-Based, and ex Vivo Assays.,  60  (1): [PMID:27966961] [10.1021/acs.jmedchem.6b01393]

7. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of MMV (CH) - Pandemic Response Box,  [10.6019/CHEMBL4513161]

8. Zhang W, Li K, Wang T, Wu M, Li L..  (2021)  Discovery of JMJD7 inhibitors with the aid of virtual screening and bioactivity evaluation.,  45  [PMID:34048880] [10.1016/j.bmcl.2021.128139]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• CO-ADD antimicrobial screening data