3-(8-fluoro-5H-pyrido[4,3-b]indol-5-yl)-1-(10H-phenothiazin-10-yl)propan-1-one

ID: ALA4864593

PubChem CID: 164624952

Max Phase: Preclinical

Molecular Formula: C26H18FN3OS

Molecular Weight: 439.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(CCn1c2ccncc2c2cc(F)ccc21)N1c2ccccc2Sc2ccccc21

Standard InChI:  InChI=1S/C26H18FN3OS/c27-17-9-10-20-18(15-17)19-16-28-13-11-21(19)29(20)14-12-26(31)30-22-5-1-3-7-24(22)32-25-8-4-2-6-23(25)30/h1-11,13,15-16H,12,14H2

Standard InChI Key:  GUDOKVFOWONHLZ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 37  0  0  0  0  0  0  0  0999 V2000
   33.2402  -26.4927    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   33.2402  -24.8583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9455  -25.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9439  -26.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6481  -26.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3544  -26.0867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3521  -25.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6473  -24.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5349  -26.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5375  -25.2728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8337  -24.8647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1270  -25.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1284  -26.0894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8327  -26.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2388  -24.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9458  -23.6313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.5304  -23.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5289  -22.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8205  -22.4092    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.0723  -22.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5260  -22.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7289  -22.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4770  -23.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0283  -23.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8234  -23.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9271  -21.4354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7277  -21.6017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2700  -20.9923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0129  -20.2163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2085  -20.0533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6697  -20.6640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6781  -23.2586    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
 10  2  1  0
  9  1  1  0
  1  4  1  0
  3  2  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  2 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 27  1  0
 26 21  1  0
 20 19  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 23 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4864593

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 439.52

Molecular Weight (Monoisotopic): 439.1155

AlogP: 6.55

#Rotatable Bonds: 3

Polar Surface Area: 38.13

Molecular Species: BASE

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.59

CX LogP: 5.13

CX LogD: 4.33

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.32

Np Likeness Score: -1.30

References

1. Schwarthoff S, Tischer N, Sager H, Schätz B, Rohrbach MM, Raztsou I, Robaa D, Gaube F, Arndt HD, Winckler T..  (2021)  Evaluation of γ-carboline-phenothiazine conjugates as simultaneous NMDA receptor blockers and cholinesterase inhibitors.,  46  [PMID:34391122] [10.1016/j.bmc.2021.116355]

Source

Source(1):

• Scientific Literature