5-[10-(1,2,3,4-Tetrahydro-acridin-9-ylamino)-decylamino]-5,6,7,8-tetrahydro-1H-quinolin-2-one

ID: ALA76658

Chembl Id: CHEMBL76658

PubChem CID: 10028957

Max Phase: Preclinical

Molecular Formula: C32H44N4O

Molecular Weight: 500.73

Molecule Type: Small molecule

Names and Identifiers

Synonyms: (RS)-Tacrine(10)-Hupyridone | (RS)-tacrine(10)-hupyridone|CHEMBL76658|BDBM50080157|5-[10-(1,2,3,4-Tetrahydro-acridin-9-ylamino)-decylamino]-5,6,7,8-tetrahydro-1H-quinolin-2-one

Canonical SMILES:  O=c1ccc2c([nH]1)CCCC2NCCCCCCCCCCNc1c2c(nc3ccccc13)CCCC2

Standard InChI:  InChI=1S/C32H44N4O/c37-31-21-20-24-27(18-13-19-28(24)36-31)33-22-11-5-3-1-2-4-6-12-23-34-32-25-14-7-9-16-29(25)35-30-17-10-8-15-26(30)32/h7,9,14,16,20-21,27,33H,1-6,8,10-13,15,17-19,22-23H2,(H,34,35)(H,36,37)

Standard InChI Key:  ROTFGKJJMRTWBD-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA76658

   (RS)-tacrine(10)-hupyridone

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: 500.73

Molecular Weight (Monoisotopic): 500.3515

AlogP: 7.00

#Rotatable Bonds: 13

Polar Surface Area: 69.81

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.33

CX Basic pKa: 9.94

CX LogP: 5.88

CX LogD: 2.28

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.22

Np Likeness Score: -0.53

References

1. Carlier PR, Du DM, Han Y, Liu J, Pang YP..  (1999)  Potent, easily synthesized huperzine A-tacrine hybrid acetylcholinesterase inhibitors.,  9  (16): [PMID:10476864] [10.1016/s0960-894x(99)00396-0]

2. Butini S, Campiani G, Borriello M, Gemma S, Panico A, Persico M, Catalanotti B, Ros S, Brindisi M, Agnusdei M, Fiorini I, Nacci V, Novellino E, Belinskaya T, Saxena A, Fattorusso C..  (2008)  Exploiting protein fluctuations at the active-site gorge of human cholinesterases: further optimization of the design strategy to develop extremely potent inhibitors.,  51  (11): [PMID:18479118] [10.1021/jm701253t]

3. Mishra P, Kumar A, Panda G..  (2019)  Anti-cholinesterase hybrids as multi-target-directed ligands against Alzheimer's disease (1998-2018).,  27  (6): [PMID:30744931] [10.1016/j.bmc.2019.01.025]

Source

Source(1):

• Scientific Literature