(1R,3R)-3-(4-(benzo[b]thiophen-3-yl)-1H-imidazol-2-yl)-1-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

ID: ALA3775284

PubChem CID: 127032662

Max Phase: Preclinical

Molecular Formula: C27H26N4OS

Molecular Weight: 454.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccc2c3c([nH]c2c1)[C@@H](C1CCOCC1)N[C@@H](c1nc(-c2csc4ccccc24)c[nH]1)C3

Standard InChI:  InChI=1S/C27H26N4OS/c1-3-7-21-17(5-1)19-13-22(30-25(26(19)29-21)16-9-11-32-12-10-16)27-28-14-23(31-27)20-15-33-24-8-4-2-6-18(20)24/h1-8,14-16,22,25,29-30H,9-13H2,(H,28,31)/t22-,25-/m1/s1

Standard InChI Key:  PAQMBKGYCRJEDT-RCZVLFRGSA-N

Molfile:  

     RDKit          2D

 33 39  0  0  0  0  0  0  0  0999 V2000
   -3.7006    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7006   -0.6045    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
   -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
    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
    2.4732   -1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372   -0.6045    0.0000 N   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
    2.4732    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0335    1.5807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1716    3.0613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6389    3.3729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3886    2.0737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3847    0.9592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4684   -2.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7672   -3.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7663   -5.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4668   -5.8201    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1682   -5.0693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1691   -3.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8811    1.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5054    0.5633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9654    0.7602    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.9396    2.9455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2501    2.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5443    2.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5046    4.5116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1941    5.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8912    4.4487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  8  5  1  0
  8  9  2  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 14  2  0
 12 14  1  6
 19 20  1  0
 19 24  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 10 19  1  6
 25 26  2  0
 26 27  1  0
 27 29  1  0
 28 25  1  0
 17 25  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3775284

   ---

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: 454.60

Molecular Weight (Monoisotopic): 454.1827

AlogP: 6.13

#Rotatable Bonds: 3

Polar Surface Area: 65.73

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.44

CX Basic pKa: 7.48

CX LogP: 4.87

CX LogD: 4.53

Aromatic Rings: 5

Heavy Atoms: 33

QED Weighted: 0.31

Np Likeness Score: -0.37

References

1. He S, Dobbelaar PH, Guo L, Ye Z, Liu J, Jian T, Truong Q, Shah SK, Du W, Qi H, Bakshi RK, Hong Q, Dellureficio JD, Sherer E, Pasternak A, Feng Z, Reibarkh M, Lin M, Samuel K, Reddy VB, Mitelman S, Tong SX, Chicchi GG, Tsao KL, Trusca D, Wu M, Shao Q, Trujillo ME, Fernandez G, Nelson D, Bunting P, Kerr J, Fitzgerald P, Morissette P, Volksdorf S, Eiermann GJ, Li C, Zhang BB, Howard AD, Zhou YP, Nargund RP, Hagmann WK..  (2016)  SAR exploration at the C-3 position of tetrahydro-β-carboline sstr3 antagonists.,  26  (6): [PMID:26898814] [10.1016/j.bmcl.2016.02.022]

Source

Source(1):

• Scientific Literature