3-{5-[6-Fluoro-9-(4-fluoro-phenyl)-1,3,4,4a,9,9a-hexahydro-beta-carbolin-2-yl]-pentyl}-imidazolidine-2,4-dione hydrochloride

ID: ALA553243

PubChem CID: 45264481

Max Phase: Preclinical

Molecular Formula: C25H29ClF2N4O2

Molecular Weight: 454.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.O=C1CNC(=O)N1CCCCCN1CC[C@@H]2c3cc(F)ccc3N(c3ccc(F)cc3)[C@H]2C1

Standard InChI:  InChI=1S/C25H28F2N4O2.ClH/c26-17-4-7-19(8-5-17)31-22-9-6-18(27)14-21(22)20-10-13-29(16-23(20)31)11-2-1-3-12-30-24(32)15-28-25(30)33;/h4-9,14,20,23H,1-3,10-13,15-16H2,(H,28,33);1H/t20-,23+;/m1./s1

Standard InChI Key:  YHKRWKWFTXFBBS-ZOLWKPHLSA-N

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
    7.5335   -2.5224    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.3190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5014   -0.5896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8551   -1.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6338    0.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8546   -0.0872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7006   -0.6045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732   -1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915   -1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0998    1.2090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1019   -2.3800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7343    1.6861    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3021   -3.5646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2029   -1.3422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0120   -5.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2900   -5.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3080   -5.0646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7737    1.4291    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.0167   -7.0197    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0029   -1.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9014   -0.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3014   -0.5998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6029   -1.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9730    1.7915    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2338   -1.6045    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  2  5  1  0
  4  6  2  0
  3  7  1  0
  5  8  1  0
  6  8  1  0
  3  9  1  0
  7 10  1  0
  2 11  1  0
  4 13  1  0
  5 14  1  0
 12 14  1  0
  8 15  1  0
  9 16  1  0
 10 16  1  0
  6 17  1  0
  7 18  2  0
  9 19  2  0
 12 20  1  0
 15 20  1  0
 11 21  2  0
 11 22  1  0
  3 23  1  0
 17 24  2  0
 13 25  2  0
 24 25  1  0
 21 27  1  0
 26 27  2  0
 22 28  2  0
 26 28  1  0
 24 29  1  0
 26 30  1  0
 12 31  1  0
 23 32  1  0
 31 33  1  0
 32 34  1  0
 33 34  1  0
  8 35  1  1
  5 36  1  6
M  END

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: 454.52

Molecular Weight (Monoisotopic): 454.2180

AlogP: 4.00

#Rotatable Bonds: 7

Polar Surface Area: 55.89

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.38

CX Basic pKa: 9.40

CX LogP: 3.56

CX LogD: 1.57

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.51

Np Likeness Score: -1.07

References

1. Sarges R, Howard HR, Donahue KM, Welch WM, Dominy BW, Weissman A, Koe BK, Bordner J..  (1986)  Neuroleptic activity of chiral trans-hexahydro-gamma-carbolines.,  29  (1): [PMID:3941416] [10.1021/jm00151a002]

Source

Source(1):

• Scientific Literature