5-((4aR,7aR)-6-(5-Fluoro-4-methoxy-6-methylpyrimidin-2-yl)-2-imino-3-methyl-4-oxooctahydro-1H-pyrrolo[3,4-d]pyrimidin-7a-yl)-thiophene-2-carbonitrile

ID: ALA3798544

Chembl Id: CHEMBL3798544

PubChem CID: 44247586

Max Phase: Preclinical

Molecular Formula: C18H18FN7O2S

Molecular Weight: 415.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1nc(N2C[C@H]3C(=O)N(C)C(=N)N[C@@]3(c3ccc(C#N)s3)C2)nc(C)c1F

Standard InChI:  InChI=1S/C18H18FN7O2S/c1-9-13(19)14(28-3)23-17(22-9)26-7-11-15(27)25(2)16(21)24-18(11,8-26)12-5-4-10(6-20)29-12/h4-5,11H,7-8H2,1-3H3,(H2,21,24)/t11-,18-/m0/s1

Standard InChI Key:  ZPAVWCJTQRQRQL-VOJFVSQTSA-N

Alternative Forms

1. Parent:

   

   ALA3798544

   5-[(2e,4ar,7ar)-6-(5-Fluoro-4-Methoxy-6-Methylpyrimidin-2-Yl)-2-Imino-3-Methyl-4-Oxooctahydro-7ah-Pyrrolo[3,4-D]pyrimidin-7a-Yl]thiophene-2-Carbonitrile

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: 415.45

Molecular Weight (Monoisotopic): 415.1227

AlogP: 1.19

#Rotatable Bonds: 3

Polar Surface Area: 118.23

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.58

CX LogP: 1.90

CX LogD: 1.90

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.77

Np Likeness Score: -0.74

References

1. Mandal M, Wu Y, Misiaszek J, Li G, Buevich A, Caldwell JP, Liu X, Mazzola RD, Orth P, Strickland C, Voigt J, Wang H, Zhu Z, Chen X, Grzelak M, Hyde LA, Kuvelkar R, Leach PT, Terracina G, Zhang L, Zhang Q, Michener MS, Smith B, Cox K, Grotz D, Favreau L, Mitra K, Kazakevich I, McKittrick BA, Greenlee W, Kennedy ME, Parker EM, Cumming JN, Stamford AW..  (2016)  Structure-Based Design of an Iminoheterocyclic β-Site Amyloid Precursor Protein Cleaving Enzyme (BACE) Inhibitor that Lowers Central Aβ in Nonhuman Primates.,  59  (7): [PMID:26937601] [10.1021/acs.jmedchem.5b01995]

Source

Source(1):

• Scientific Literature