2-methoxy-N-(3-phenylpropyl)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-7-amine

ID: ALA3357784

Chembl Id: CHEMBL3357784

PubChem CID: 86302361

Max Phase: Preclinical

Molecular Formula: C21H27NO

Molecular Weight: 309.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)CCC(NCCCc1ccccc1)CC2

Standard InChI:  InChI=1S/C21H27NO/c1-23-21-14-11-18-9-12-20(13-10-19(18)16-21)22-15-5-8-17-6-3-2-4-7-17/h2-4,6-7,11,14,16,20,22H,5,8-10,12-13,15H2,1H3

Standard InChI Key:  DCBAUCRPRDYNOG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3357784

   3-methoxy-N-(3-phenylpropyl)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-7-amine

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: 309.45

Molecular Weight (Monoisotopic): 309.2093

AlogP: 4.17

#Rotatable Bonds: 6

Polar Surface Area: 21.26

Molecular Species: BASE

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.78

CX LogP: 5.11

CX LogD: 2.10

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.64

Np Likeness Score: -0.31

References

1. Gawaskar S, Schepmann D, Bonifazi A, Wünsch B..  (2014)  Synthesis, GluN2B affinity and selectivity of benzo[7]annulen-7-amines.,  22  (23): [PMID:25458498] [10.1016/j.bmc.2014.10.004]

2. Gawaskar S, Schepmann D, Bonifazi A, Robaa D, Sippl W, Wünsch B..  (2015)  Benzo[7]annulene-based GluN2B selective NMDA receptor antagonists: Surprising effect of a nitro group in 2-position.,  25  (24): [PMID:26531150] [10.1016/j.bmcl.2015.10.076]

3. Shuto Y, Thum S, Temme L, Schepmann D, Kitamura M, Wünsch B..  (2017)  Do GluN2B subunit containing NMDA receptors tolerate a fluorine atom in the phenylalkyl side chain?,  8  (5): [PMID:30108812] [10.1039/C6MD00621C]

4. Zscherp R, Baumeister S, Schepmann D, Wünsch B..  (2018)  Pyridine bioisosteres of potent GluN2B subunit containing NMDA receptor antagonists with benzo[7]annulene scaffold.,  157  [PMID:30103189] [10.1016/j.ejmech.2018.08.003]

5. Temme L, Börgel F, Schepmann D, Robaa D, Sippl W, Daniliuc C, Wünsch B..  (2019)  Impact of hydroxy moieties at the benzo[7]annulene ring system of GluN2B ligands: Design, synthesis and biological evaluation.,  27  (23): [PMID:31648876] [10.1016/j.bmc.2019.115146]

Source

Source(1):

• Scientific Literature