ID: ALA3087936

Max Phase: Preclinical

Molecular Formula: C16H17N3O7P2S

Molecular Weight: 457.34

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=P(O)(O)C(Nc1ncnc2sc(-c3ccc(OC4CC4)cc3)cc12)P(=O)(O)O

Standard InChI:  InChI=1S/C16H17N3O7P2S/c20-27(21,22)16(28(23,24)25)19-14-12-7-13(29-15(12)18-8-17-14)9-1-3-10(4-2-9)26-11-5-6-11/h1-4,7-8,11,16H,5-6H2,(H,17,18,19)(H2,20,21,22)(H2,23,24,25)

Standard InChI Key:  PQMXODSLXCHEMQ-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: 457.34

Molecular Weight (Monoisotopic): 457.0262

AlogP: 2.95

#Rotatable Bonds: 7

Polar Surface Area: 162.10

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 0.88

CX Basic pKa: 3.94

CX LogP: -0.27

CX LogD: -3.13

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.33

Np Likeness Score: -0.74

References

1. Leung CY, Park J, De Schutter JW, Sebag M, Berghuis AM, Tsantrizos YS..  (2013)  Thienopyrimidine bisphosphonate (ThPBP) inhibitors of the human farnesyl pyrophosphate synthase: optimization and characterization of the mode of inhibition.,  56  (20): [PMID:23998921] [10.1021/jm400946f]

2. De Schutter JW, Park J, Leung CY, Gormley P, Lin YS, Hu Z, Berghuis AM, Poirier J, Tsantrizos YS..  (2014)  Multistage screening reveals chameleon ligands of the human farnesyl pyrophosphate synthase: implications to drug discovery for neurodegenerative diseases.,  57  (13): [PMID:24911527] [10.1021/jm500629e]

Source

Source(1):

• Scientific Literature