ID: ALA2088339

Max Phase: Preclinical

Molecular Formula: C15H18N2O7P2

Molecular Weight: 400.26

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=P(O)(O)C(Nc1cncc(-c2ccc(OC3CC3)cc2)c1)P(=O)(O)O

Standard InChI:  InChI=1S/C15H18N2O7P2/c18-25(19,20)15(26(21,22)23)17-12-7-11(8-16-9-12)10-1-3-13(4-2-10)24-14-5-6-14/h1-4,7-9,14-15,17H,5-6H2,(H2,18,19,20)(H2,21,22,23)

Standard InChI Key:  QCLQOQRSHDMFKS-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: 400.26

Molecular Weight (Monoisotopic): 400.0589

AlogP: 2.34

#Rotatable Bonds: 7

Polar Surface Area: 149.21

Molecular Species: ACID

HBA: 5

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 0.92

CX Basic pKa: 2.71

CX LogP: -0.55

CX LogD: -4.09

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: -0.39

References

1. De Schutter JW, Shaw J, Lin YS, Tsantrizos YS..  (2012)  Design of potent bisphosphonate inhibitors of the human farnesyl pyrophosphate synthase via targeted interactions with the active site 'capping' phenyls.,  20  (18): [PMID:22884353] [10.1016/j.bmc.2012.07.019]

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