Phenyl-carbamic acid 2-[8-fluoro-5-(4-fluoro-phenyl)-1,3,4,4a,5,9b-hexahydro-pyrido[4,3-b]indol-2-yl]-ethyl ester hydrochloride

ID: ALA538242

PubChem CID: 45264437

Max Phase: Preclinical

Molecular Formula: C26H26ClF2N3O2

Molecular Weight: 449.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.O=C(Nc1ccccc1)OCCN1CC[C@H]2[C@H](C1)c1cc(F)ccc1N2c1ccc(F)cc1

Standard InChI:  InChI=1S/C26H25F2N3O2.ClH/c27-18-6-9-21(10-7-18)31-24-11-8-19(28)16-22(24)23-17-30(13-12-25(23)31)14-15-33-26(32)29-20-4-2-1-3-5-20;/h1-11,16,23,25H,12-15,17H2,(H,29,32);1H/t23-,25+;/m1./s1

Standard InChI Key:  LZIXFYUNFGQDSI-BUDDBBPTSA-N

Molfile:  

     RDKit          2D

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    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
   -1.2274    0.8244    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   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -10.2029    1.5620    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2900   -5.0749    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    1.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3014    0.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.8033    1.5546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4959   -0.6906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7922   -1.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0995    0.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0940   -0.7001    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
  3  4  1  0
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  8 20  1  0
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 19 21  1  0
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 18 24  2  0
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  3 35  1  1
  4 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: 449.50

Molecular Weight (Monoisotopic): 449.1915

AlogP: 5.52

#Rotatable Bonds: 5

Polar Surface Area: 44.81

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.04

CX Basic pKa: 7.22

CX LogP: 5.25

CX LogD: 5.03

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.56

Np Likeness Score: -1.30

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