9-(3-(4-Chlorophenoxy)propyl)-6-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole 2,2,2-trifluoroacetic acid

ID: ALA4475183

PubChem CID: 155537476

Max Phase: Preclinical

Molecular Formula: C23H24ClF3N2O3

Molecular Weight: 354.88

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1ccc2c(c1)c1c(n2CCCOc2ccc(Cl)cc2)CNCC1.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C21H23ClN2O.C2HF3O2/c1-15-3-8-20-19(13-15)18-9-10-23-14-21(18)24(20)11-2-12-25-17-6-4-16(22)5-7-17;3-2(4,5)1(6)7/h3-8,13,23H,2,9-12,14H2,1H3;(H,6,7)

Standard InChI Key:  OAYKIIBUCYZSBN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   19.3527  -20.8338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0604  -20.4252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7681  -20.8338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0604  -19.6080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6204  -21.2645    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.5545  -20.5303    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.3273  -21.7046    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   14.6421  -19.1464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2296  -20.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9774  -19.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1747  -19.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6234  -20.0728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8803  -20.8577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6824  -21.0258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3114  -19.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0488  -20.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5961  -21.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4088  -20.8739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6714  -20.0869    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1213  -19.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6403  -18.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3539  -17.9074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3522  -17.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0658  -16.6683    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7812  -17.0793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7787  -17.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4932  -18.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2078  -17.9026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2034  -17.0733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4883  -16.6662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9237  -18.3127    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   12.3299  -21.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  1  5  1  0
  1  6  1  0
  1  7  1  0
  9 16  1  0
 15  8  1  0
  8 10  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
 15 16  2  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  8 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 28 31  1  0
 13 32  1  0
M  END

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: 354.88

Molecular Weight (Monoisotopic): 354.1499

AlogP: 4.72

#Rotatable Bonds: 5

Polar Surface Area: 26.19

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.04

CX LogP: 4.64

CX LogD: 3.00

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.67

Np Likeness Score: -1.01

References

1. Tu J, Li Z, Jiang Y, Ji C, Han G, Wang Y, Liu N, Sheng C..  (2019)  Discovery of Carboline Derivatives as Potent Antifungal Agents for the Treatment of Cryptococcal Meningitis.,  62  (5): [PMID:30753074] [10.1021/acs.jmedchem.8b01598]

Source

Source(1):

• Scientific Literature