ID: ALA2347862

Max Phase: Preclinical

Molecular Formula: C14H15N3O6P2S

Molecular Weight: 415.30

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1ccc(-c2cc3c(NC(P(=O)(O)O)P(=O)(O)O)ncnc3s2)cc1

Standard InChI:  InChI=1S/C14H15N3O6P2S/c1-8-2-4-9(5-3-8)11-6-10-12(15-7-16-13(10)26-11)17-14(24(18,19)20)25(21,22)23/h2-7,14H,1H3,(H,15,16,17)(H2,18,19,20)(H2,21,22,23)

Standard InChI Key:  SFWLGYOMOJOLFV-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: 415.30

Molecular Weight (Monoisotopic): 415.0157

AlogP: 2.72

#Rotatable Bonds: 5

Polar Surface Area: 152.87

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 0.89

CX Basic pKa: 3.83

CX LogP: -0.01

CX LogD: -2.87

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.40

Np Likeness Score: -1.08

References

1. Leung CY, Langille AM, Mancuso J, Tsantrizos YS..  (2013)  Discovery of thienopyrimidine-based inhibitors of the human farnesyl pyrophosphate synthase--parallel synthesis of analogs via a trimethylsilyl ylidene intermediate.,  21  (8): [PMID:23477945] [10.1016/j.bmc.2013.02.006]

2. 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]

3. 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