ID: ALA572934

Max Phase: Preclinical

Molecular Formula: C17H18N4O

Molecular Weight: 294.36

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=c1[nH]c(Cc2ccccc2)nc2c1cnn2C1CCCC1

Standard InChI:  InChI=1S/C17H18N4O/c22-17-14-11-18-21(13-8-4-5-9-13)16(14)19-15(20-17)10-12-6-2-1-3-7-12/h1-3,6-7,11,13H,4-5,8-10H2,(H,19,20,22)

Standard InChI Key:  FVOYQCUKGQGDKH-UHFFFAOYSA-N

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

Properties

Molecular Weight: 294.36

Molecular Weight (Monoisotopic): 294.1481

AlogP: 2.83

#Rotatable Bonds: 3

Polar Surface Area: 63.57

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.16

CX Basic pKa: 0.17

CX LogP: 2.48

CX LogD: 2.47

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.81

Np Likeness Score: -1.38

References

1. Verhoest PR, Proulx-Lafrance C, Corman M, Chenard L, Helal CJ, Hou X, Kleiman R, Liu S, Marr E, Menniti FS, Schmidt CJ, Vanase-Frawley M, Schmidt AW, Williams RD, Nelson FR, Fonseca KR, Liras S..  (2009)  Identification of a brain penetrant PDE9A inhibitor utilizing prospective design and chemical enablement as a rapid lead optimization strategy.,  52  (24): [PMID:19919087] [10.1021/jm9015334]

2. Claffey MM, Helal CJ, Verhoest PR, Kang Z, Fors KS, Jung S, Zhong J, Bundesmann MW, Hou X, Lui S, Kleiman RJ, Vanase-Frawley M, Schmidt AW, Menniti F, Schmidt CJ, Hoffman WE, Hajos M, McDowell L, O'Connor RE, Macdougall-Murphy M, Fonseca KR, Becker SL, Nelson FR, Liras S..  (2012)  Application of structure-based drug design and parallel chemistry to identify selective, brain penetrant, in vivo active phosphodiesterase 9A inhibitors.,  55  (21): [PMID:23025719] [10.1021/jm3009635]

3. Verhoest PR, Fonseca KR, Hou X, Proulx-Lafrance C, Corman M, Helal CJ, Claffey MM, Tuttle JB, Coffman KJ, Liu S, Nelson F, Kleiman RJ, Menniti FS, Schmidt CJ, Vanase-Frawley M, Liras S..  (2012)  Design and discovery of 6-[(3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (PF-04447943), a selective brain penetrant PDE9A inhibitor for the treatment of cognitive disorders.,  55  (21): [PMID:22780914] [10.1021/jm3007799]

Source

Source(1):

• Scientific Literature