(4'S)-2-((2a-ethyl-4-oxo-2a,3,4,5-tetrahydropyrrolo[4,3,2-de]quinolin-1(2H)-yl)methyl)-3'-methyl-6,8-dihydrospiro[cyclopenta[g]quinoline-7,4'-imidazolidine]-2',5'-dione

ID: ALA1089772

PubChem CID: 46885245

Max Phase: Preclinical

Molecular Formula: C28H27N5O3

Molecular Weight: 481.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC12CC(=O)Nc3cccc(c31)N(Cc1ccc3cc4c(cc3n1)C[C@@]1(C4)C(=O)NC(=O)N1C)C2

Standard InChI:  InChI=1S/C28H27N5O3/c1-3-27-13-23(34)30-20-5-4-6-22(24(20)27)33(15-27)14-19-8-7-16-9-17-11-28(12-18(17)10-21(16)29-19)25(35)31-26(36)32(28)2/h4-10H,3,11-15H2,1-2H3,(H,30,34)(H,31,35,36)/t27?,28-/m0/s1

Standard InChI Key:  YTNSSBQNYOFYGN-CPRJBALCSA-N

Molfile:  

     RDKit          2D

 36 42  0  0  0  0  0  0  0  0999 V2000
   20.8626  -19.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3852  -20.5711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1539  -20.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1065  -19.4476    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3084  -19.2382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8466  -20.6585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9215  -19.0098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6203  -19.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5787  -20.2776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3469  -20.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4141  -19.2424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0087  -18.4694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.8483  -20.7172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1756  -21.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1556  -20.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1875  -19.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7372  -20.2782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2680  -20.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2669  -21.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9818  -22.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6984  -21.7272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6967  -20.9019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3118  -20.3487    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9763  -19.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0466  -20.7241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4655  -20.6552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3786  -19.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6915  -19.4608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9800  -20.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1567  -19.6814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5505  -19.1286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7642  -19.3762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5875  -20.1820    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1552  -18.8192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3655  -18.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7778  -18.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
 18 19  2  0
  3  4  1  0
 19 20  1  0
  4  5  1  0
 20 21  2  0
 21 22  1  0
 29 18  1  0
 29 22  2  0
  1  5  1  1
  9 10  1  0
 10  1  1  0
 22 23  1  0
 23 24  1  0
 24 30  1  0
  1 11  1  0
 11  8  1  0
 23 25  1  0
 25 17  1  0
  1  2  1  0
 17 26  2  0
 26 15  1  0
  5 12  2  0
 16 27  1  0
 15  6  2  0
 27 28  2  0
 28 17  1  0
 29 30  1  0
  3 13  2  0
  6  9  1  0
  2 14  1  0
 15 16  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 18  1  0
  8  7  1  0
 32 34  2  0
  7 16  2  0
 30 35  1  0
  8  9  2  0
 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1089772

   (7S)-2-[(4-ethyl-6-oxo-2,7-diazatricyclo[6.3.1.04,12]dodeca-1(11),8(12),9-trien-2-yl)methyl]-1'-methylspiro[6,8-dihydrocyclopenta[g]quinoline-7,5'-imidazolidine]-2',4'-dione

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: 481.56

Molecular Weight (Monoisotopic): 481.2114

AlogP: 3.26

#Rotatable Bonds: 3

Polar Surface Area: 94.64

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.45

CX Basic pKa: 3.18

CX LogP: 3.00

CX LogD: 3.00

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.56

Np Likeness Score: -0.24

References

1. Stump CA, Bell IM, Bednar RA, Fay JF, Gallicchio SN, Hershey JC, Jelley R, Kreatsoulas C, Moore EL, Mosser SD, Quigley AG, Roller SA, Salvatore CA, Sharik SS, Theberge CR, Zartman CB, Kane SA, Graham SL, Selnick HG, Vacca JP, Williams TM..  (2010)  Identification of potent, highly constrained CGRP receptor antagonists.,  20  (8): [PMID:20299218] [10.1016/j.bmcl.2010.02.086]

Source

Source(1):

• Scientific Literature