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

ID: ALA540282

PubChem CID: 45264462

Max Phase: Preclinical

Molecular Formula: C26H31ClF2N4O2

Molecular Weight: 468.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.O=C1CNC(=O)N1CCCCCCN1CC[C@@H]2c3cc(F)ccc3N(c3ccc(F)cc3)[C@H]2C1

Standard InChI:  InChI=1S/C26H30F2N4O2.ClH/c27-18-5-8-20(9-6-18)32-23-10-7-19(28)15-22(23)21-11-14-30(17-24(21)32)12-3-1-2-4-13-31-25(33)16-29-26(31)34;/h5-10,15,21,24H,1-4,11-14,16-17H2,(H,29,34);1H/t21-,24+;/m1./s1

Standard InChI Key:  LHJGMBPSLULHJD-WKDBURHASA-N

Molfile:  

     RDKit          2D

 37 40  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
  -12.8028   -1.3371    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
  -14.1541   -0.7158    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
  -12.9410   -2.8179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.1580   -1.8303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -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
  -14.4083   -3.1295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -14.3963    0.4595    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
  -11.5014   -0.5896    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
  -10.2029   -1.3422    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
   -8.9014   -0.5947    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
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 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 35  1  0
 34 35  1  0
  8 36  1  1
  5 37  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: 468.55

Molecular Weight (Monoisotopic): 468.2337

AlogP: 4.39

#Rotatable Bonds: 8

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: 12.32

CX Basic pKa: 9.42

CX LogP: 4.00

CX LogD: 1.99

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.46

Np Likeness Score: -1.04

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