8-{4-[3-(1H-Indol-3-yl)-propyl]-piperazin-1-yl}-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

ID: ALA199045

Chembl Id: CHEMBL199045

PubChem CID: 11553516

Max Phase: Preclinical

Molecular Formula: C25H30N4O2

Molecular Weight: 418.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2c(cccc2N2CCN(CCCc3c[nH]c4ccccc34)CC2)NC1=O

Standard InChI:  InChI=1S/C25H30N4O2/c1-25(2)24(30)27-21-10-5-11-22(23(21)31-25)29-15-13-28(14-16-29)12-6-7-18-17-26-20-9-4-3-8-19(18)20/h3-5,8-11,17,26H,6-7,12-16H2,1-2H3,(H,27,30)

Standard InChI Key:  NXIWXBJHNOSEDP-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA199045

   8-{4-[3-(1H-Indol-3-yl)-propyl]-piperazin-1-yl}-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

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: 418.54

Molecular Weight (Monoisotopic): 418.2369

AlogP: 4.03

#Rotatable Bonds: 5

Polar Surface Area: 60.60

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.42

CX Basic pKa: 8.34

CX LogP: 4.27

CX LogD: 3.29

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.66

Np Likeness Score: -0.47

References

1. Smid P, Coolen HK, Keizer HG, van Hes R, de Moes JP, den Hartog AP, Stork B, Plekkenpol RH, Niemann LC, Stroomer CN, Tulp MT, van Stuivenberg HH, McCreary AC, Hesselink MB, Herremans AH, Kruse CG..  (2005)  Synthesis, structure-activity relationships, and biological properties of 1-heteroaryl-4-[omega-(1H-indol-3-yl)alkyl]piperazines, novel potential antipsychotics combining potent dopamine D2 receptor antagonism with potent serotonin reuptake inhibition.,  48  (22): [PMID:16250644] [10.1021/jm050148z]

Source

Source(1):

• Scientific Literature