(R-5135) 3-Hydroxy-16-imino-10,13-dimethyl-11-oxo-hexadecahydro-17-azonia-cyclopenta[a]phenanthrene

ID: ALA1161036

PubChem CID: 44353719

Max Phase: Preclinical

Molecular Formula: C18H28N2O2

Molecular Weight: 304.43

Molecule Type: Small molecule

Names and Identifiers

Synonyms: R-5135 | R-5135|CHEMBL1161036

Canonical SMILES:  C[C@]12CC(=O)C3C(CC[C@@H]4C[C@H](O)CC[C@]34C)C1CC(=N)N2

Standard InChI:  InChI=1S/C18H28N2O2/c1-17-6-5-11(21)7-10(17)3-4-12-13-8-15(19)20-18(13,2)9-14(22)16(12)17/h10-13,16,21H,3-9H2,1-2H3,(H2,19,20)/t10-,11-,12?,13?,16?,17+,18+/m1/s1

Standard InChI Key:  LLAKESJIQFAQJA-AORADPIQSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    1.9750   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5500   -0.9292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9250   -1.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9250   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -0.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208   -1.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5375   -1.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917   -1.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -0.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9167   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1208   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -0.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6333   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6333   -2.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000   -1.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1500   -2.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000   -3.1917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  6  1  0
  4  3  1  0
  5  7  1  0
  6  8  1  0
  7  1  1  0
  8  1  1  0
  9  2  1  0
 10  4  1  0
 11  5  1  0
 12  4  1  0
 13  7  1  0
 14  9  2  0
 15  6  2  0
 16 11  1  0
 17 10  1  0
  1 18  1  1
 19 12  1  0
 20 19  1  0
  4 21  1  1
 20 22  1  6
 10 23  1  1
 13  9  1  0
  3  5  1  0
 10 16  1  0
 17 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1161036

   (5aR,7R,9aS,11aS)-2-amino-7-hydroxy-9a,11a-dimethyl-3,3a,3b,4,5,5a,6,7,8,9,9b,11-dodecahydronaphtho[2,1-e]indol-10-one

Molecule Features

Natural Product: Yes

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: 304.43

Molecular Weight (Monoisotopic): 304.2151

AlogP: 2.50

#Rotatable Bonds: ┄

Polar Surface Area: 73.18

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 11.79

CX LogP: 1.25

CX LogD: -1.16

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.64

Np Likeness Score: 2.04

References

1. Melikian A, Schlewer G, Chambon JP, Wermuth CG..  (1992)  Condensation of muscimol or thiomuscimol with aminopyridazines yields GABA-A antagonists.,  35  (22): [PMID:1331456] [10.1021/jm00100a015]

Source

Source(1):

• Scientific Literature