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

ID: ALA3735947

Chembl Id: CHEMBL3735947

PubChem CID: 127034646

Max Phase: Preclinical

Molecular Formula: C20H24N2O2

Molecular Weight: 324.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1ccc2c(c1)CCC(NCCCc1ccccc1)CC2

Standard InChI:  InChI=1S/C20H24N2O2/c23-22(24)20-13-10-17-8-11-19(12-9-18(17)15-20)21-14-4-7-16-5-2-1-3-6-16/h1-3,5-6,10,13,15,19,21H,4,7-9,11-12,14H2

Standard InChI Key:  ZCIHOOYQUGPXHZ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA3735947

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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: 324.42

Molecular Weight (Monoisotopic): 324.1838

AlogP: 4.06

#Rotatable Bonds: 6

Polar Surface Area: 55.17

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.68

CX LogP: 5.21

CX LogD: 2.25

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.38

Np Likeness Score: -0.81

References

1. 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]

2. Baumeister S, Schepmann D, Wünsch B..  (2020)  Thiophene bioisosteres of GluN2B selective NMDA receptor antagonists: Synthesis and pharmacological evaluation of [7]annuleno[b]thiophen-6-amines.,  28  (2): [PMID:31843460] [10.1016/j.bmc.2019.115245]

Source

Source(1):

• Scientific Literature