(1S,2S,4R)-Bicyclo[2.2.1]hept-2-yl-(2,4,8a,9-tetraaza-fluoren-1-yl)-amine

ID: ALA3786174

PubChem CID: 127033321

Max Phase: Preclinical

Molecular Formula: C16H17N5

Molecular Weight: 279.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  c1ccn2nc3c(N[C@H]4C[C@@H]5CC[C@H]4C5)ncnc3c2c1

Standard InChI:  InChI=1S/C16H17N5/c1-2-6-21-13(3-1)14-15(20-21)16(18-9-17-14)19-12-8-10-4-5-11(12)7-10/h1-3,6,9-12H,4-5,7-8H2,(H,17,18,19)/t10-,11+,12+/m1/s1

Standard InChI Key:  KQNFMYWDXNSOHC-WOPDTQHZSA-N

Molfile:  

     RDKit          2D

 23 27  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
   -3.8708   -5.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1961   -5.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4447   -4.9592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3833   -3.4829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0889   -2.7704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4616   -4.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0207   -5.5657    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2335   -2.9563    0.0000 H   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
  1 15  1  6
  1 16  1  0
  1 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 16 21  1  0
 19 21  1  0
 16 22  1  6
 19 23  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3786174

   ---

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: 279.35

Molecular Weight (Monoisotopic): 279.1484

AlogP: 2.88

#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: 2.95

CX LogD: 2.95

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.78

Np Likeness Score: -1.09

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