ID: ALA60048

Max Phase: Preclinical

Molecular Formula: C24H32N2O4

Molecular Weight: 412.53

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cc2c(cc1OC)CN(CCCCNC(=O)c1cc(C)ccc1OC)CC2

Standard InChI:  InChI=1S/C24H32N2O4/c1-17-7-8-21(28-2)20(13-17)24(27)25-10-5-6-11-26-12-9-18-14-22(29-3)23(30-4)15-19(18)16-26/h7-8,13-15H,5-6,9-12,16H2,1-4H3,(H,25,27)

Standard InChI Key:  KOEMMHBJOHMMBF-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: 412.53

Molecular Weight (Monoisotopic): 412.2362

AlogP: 3.59

#Rotatable Bonds: 9

Polar Surface Area: 60.03

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 8.00

CX LogP: 3.45

CX LogD: 2.75

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.64

Np Likeness Score: -0.94

References

1. Mach RH, Huang Y, Freeman RA, Wu L, Vangveravong S, Luedtke RR..  (2004)  Conformationally-flexible benzamide analogues as dopamine D3 and sigma 2 receptor ligands.,  14  (1): [PMID:14684327] [10.1016/j.bmcl.2003.09.083]

2. Colabufo NA, Abate C, Contino M, Inglese C, Ferorelli S, Berardi F, Perrone R..  (2008)  Tritium radiolabelling of PB28, a potent sigma-2 receptor ligand: pharmacokinetic and pharmacodynamic characterization.,  18  (6): [PMID:18178434] [10.1016/j.bmcl.2007.12.056]

3. Mach RH, Zeng C, Hawkins WG..  (2013)  The σ2 receptor: a novel protein for the imaging and treatment of cancer.,  56  (18): [PMID:23734634] [10.1021/jm301545c]

4. Bai S, Li S, Xu J, Peng X, Sai K, Chu W, Tu Z, Zeng C, Mach RH..  (2014)  Synthesis and structure-activity relationship studies of conformationally flexible tetrahydroisoquinolinyl triazole carboxamide and triazole substituted benzamide analogues as σ2 receptor ligands.,  57  (10): [PMID:24821398] [10.1021/jm5001453]

5. Sun YT, Wang GF, Yang YQ, Jin F, Wang Y, Xie XY, Mach RH, Huang YS..  (2018)  Synthesis and pharmacological evaluation of 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline derivatives as sigma-2 receptor ligands.,  147  [PMID:29438891] [10.1016/j.ejmech.2017.11.016]

6. Xie XY,Li YY,Ma WH,Chen AF,Sun YT,Lee JY,Riad A,Xu DH,Mach RH,Huang YS.  (2021)  Synthesis, binding, and functional properties of tetrahydroisoquinolino-2-alkyl phenones as selective σR/TMEM97 ligands.,  209  [PMID:33049607] [10.1016/j.ejmech.2020.112906]

Source

Source(1):

• Scientific Literature