9-[N-gamma-(2'-(nitrooxy)acetyl)-gamma-aminopropylamino]-1,2,3,4-tetrahydroacridine

ID: ALA269865

Chembl Id: CHEMBL269865

PubChem CID: 24800130

Max Phase: Preclinical

Molecular Formula: C18H22N4O4

Molecular Weight: 358.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CO[N+](=O)[O-])NCCCNc1c2c(nc3ccccc13)CCCC2

Standard InChI:  InChI=1S/C18H22N4O4/c23-17(12-26-22(24)25)19-10-5-11-20-18-13-6-1-3-8-15(13)21-16-9-4-2-7-14(16)18/h1,3,6,8H,2,4-5,7,9-12H2,(H,19,23)(H,20,21)

Standard InChI Key:  FWBFWRIDEUVUDF-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA269865

   2-Nitrooxy-N-[3-(1,2,3,4-tetrahydro-acridin-9-ylamino)-propyl]-acetamide

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: 358.40

Molecular Weight (Monoisotopic): 358.1641

AlogP: 2.24

#Rotatable Bonds: 8

Polar Surface Area: 106.39

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.89

CX LogP: 1.89

CX LogD: 0.56

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.43

Np Likeness Score: -1.18

References

1. Fang L, Appenroth D, Decker M, Kiehntopf M, Roegler C, Deufel T, Fleck C, Peng S, Zhang Y, Lehmann J..  (2008)  Synthesis and biological evaluation of NO-donor-tacrine hybrids as hepatoprotective anti-Alzheimer drug candidates.,  51  (4): [PMID:18232655] [10.1021/jm701491k]

2. Fang L, Appenroth D, Decker M, Kiehntopf M, Lupp A, Peng S, Fleck C, Zhang Y, Lehmann J..  (2008)  NO-donating tacrine hybrid compounds improve scopolamine-induced cognition impairment and show less hepatotoxicity.,  51  (24): [PMID:19053746] [10.1021/jm801131a]

Source

Source(1):

• Scientific Literature