ID: ALA1938681

Max Phase: Preclinical

Molecular Formula: C27H25ClN4O2

Molecular Weight: 472.98

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(c1ccc(-c2ccc(Cl)cc2)o1)N(Cc1ccccn1)c1ccc(N2CCNCC2)cc1

Standard InChI:  InChI=1S/C27H25ClN4O2/c28-21-6-4-20(5-7-21)25-12-13-26(34-25)27(33)32(19-22-3-1-2-14-30-22)24-10-8-23(9-11-24)31-17-15-29-16-18-31/h1-14,29H,15-19H2

Standard InChI Key:  LIPNXDIBECKOMJ-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: 472.98

Molecular Weight (Monoisotopic): 472.1666

AlogP: 5.25

#Rotatable Bonds: 6

Polar Surface Area: 61.61

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 8.88

CX LogP: 4.32

CX LogD: 2.83

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.41

Np Likeness Score: -1.85

References

1. Rao AU, Xiao D, Huang X, Zhou W, Fossetta J, Lundell D, Tian F, Trivedi P, Aslanian R, Palani A..  (2012)  Facile synthesis of tetracyclic azepine and oxazocine derivatives and their potential as MAPKAP-K2 (MK2) inhibitors.,  22  (2): [PMID:22182499] [10.1016/j.bmcl.2011.11.113]

2. Huang X, Zhu X, Chen X, Zhou W, Xiao D, Degrado S, Aslanian R, Fossetta J, Lundell D, Tian F, Trivedi P, Palani A..  (2012)  A three-step protocol for lead optimization: quick identification of key conformational features and functional groups in the SAR studies of non-ATP competitive MK2 (MAPKAPK2) inhibitors.,  22  (1): [PMID:22169260] [10.1016/j.bmcl.2011.11.074]

3. Huang X, Shipps GW, Cheng CC, Spacciapoli P, Zhang X, McCoy MA, Wyss DF, Yang X, Achab A, Soucy K, Montavon DK, Murphy DM, Whitehurst CE..  (2011)  Discovery and Hit-to-Lead Optimization of Non-ATP Competitive MK2 (MAPKAPK2) Inhibitors.,  2  (8): [PMID:24900358] [10.1021/ml200113y]

4. Qin J, Dhondi P, Huang X, Aslanian R, Fossetta J, Tian F, Lundell D, Palani A..  (2012)  Discovery of a Potent Dihydrooxadiazole Series of Non-ATP-Competitive MK2 (MAPKAPK2) Inhibitors.,  3  (2): [PMID:24900435] [10.1021/ml200238g]

5. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

6. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

Source

Source(3):

• Scientific Literature
• AstraZeneca Deposited Data
• Fraunhofer HDAC6