trans-N'3,N'3-Dimethyl-N'1-(4-methyl-cyclohexyl)-2,4,8a,9-tetraaza-fluorene-1,3-diamine

ID: ALA3785968

PubChem CID: 127034280

Max Phase: Preclinical

Molecular Formula: C18H24N6

Molecular Weight: 324.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1nc(N[C@H]2CC[C@H](C)CC2)c2nn3ccccc3c2n1

Standard InChI:  InChI=1S/C18H24N6/c1-12-7-9-13(10-8-12)19-17-16-15(20-18(21-17)23(2)3)14-6-4-5-11-24(14)22-16/h4-6,11-13H,7-10H2,1-3H3,(H,19,20,21)/t12-,13-

Standard InChI Key:  VYSYKARGHFFYJV-JOCQHMNTSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   -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
   -3.8372   -3.5442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8705   -5.0438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1859   -5.7649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4680   -4.9863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4347   -3.4867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1194   -2.7656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5202   -5.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9998    1.5775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9984    2.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0400    0.9791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  6  1  0
  5  4  1  0
  4  1  2  0
  5  6  1  0
  6  9  2  0
  8  7  1  0
  7  5  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  4 14  1  0
 15 14  1  1
 15 16  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  6
  2 22  1  0
 22 23  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3785968

   ---

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: 324.43

Molecular Weight (Monoisotopic): 324.2062

AlogP: 3.33

#Rotatable Bonds: 3

Polar Surface Area: 58.35

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.26

CX LogP: 4.28

CX LogD: 4.28

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.80

Np Likeness Score: -1.32

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