Adamantan-2-yl-(2,4,8a,9-tetraaza-fluoren-1-yl)-amine

ID: ALA3786284

PubChem CID: 127034283

Max Phase: Preclinical

Molecular Formula: C19H21N5

Molecular Weight: 319.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccn2nc3c(NC4C5CC6CC(C5)CC4C6)ncnc3c2c1

Standard InChI:  InChI=1S/C19H21N5/c1-2-4-24-15(3-1)17-18(23-24)19(21-10-20-17)22-16-13-6-11-5-12(8-13)9-14(16)7-11/h1-4,10-14,16H,5-9H2,(H,20,21,22)

Standard InChI Key:  ZRTSMEPGGWNWDK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 29  0  0  0  0  0  0  0  0999 V2000
   -3.8372   -3.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7006   -0.6045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7006    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915    1.5389    0.0000 N   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
   -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
    0.0000   -1.3190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -0.6045    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
    2.4732    1.5389    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
    2.4732   -1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5225   -2.8202    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2974   -5.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8231   -4.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8754   -4.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4233   -2.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0200   -2.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4929   -6.0224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6465   -5.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0438   -4.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1537   -3.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  2  0
  4  7  1  0
  6  5  1  0
  5  2  2  0
  6  7  1  0
  7 10  2  0
  9  8  1  0
  8  6  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  5 15  1  0
 15  1  1  0
 16 17  1  0
 16 18  1  0
 17 19  1  0
 18  1  1  0
 19 20  1  0
  1 20  1  0
 21 22  1  0
 18 21  1  0
 17 23  1  0
 20 24  1  0
 24 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3786284

   ---

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: 319.41

Molecular Weight (Monoisotopic): 319.1797

AlogP: 3.51

#Rotatable Bonds: 2

Polar Surface Area: 55.11

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.74

CX LogP: 3.58

CX LogD: 3.58

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.79

Np Likeness Score: -1.02

References

1. Felts AS, Rodriguez AL, Morrison RD, Venable DF, Blobaum AL, Byers FW, Daniels JS, Niswender CM, Jones CK, Conn PJ, Lindsley CW, Emmitte KA..  (2016)  N-Alkylpyrido[1',2':1,5]pyrazolo-[4,3-d]pyrimidin-4-amines: A new series of negative allosteric modulators of mGlu1/5 with CNS exposure in rodents.,  26  (8): [PMID:26988308] [10.1016/j.bmcl.2016.03.026]

Source

Source(1):

• Scientific Literature