ID: ALA1231307

Max Phase: Preclinical

Molecular Formula: C15H11NO4

Molecular Weight: 269.26

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(O)Cn1c(C(=O)O)cc2ccc3ccccc3c21

Standard InChI:  InChI=1S/C15H11NO4/c17-13(18)8-16-12(15(19)20)7-10-6-5-9-3-1-2-4-11(9)14(10)16/h1-7H,8H2,(H,17,18)(H,19,20)

Standard InChI Key:  AKGLRHRNGGDMDM-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: 269.26

Molecular Weight (Monoisotopic): 269.0688

AlogP: 2.58

#Rotatable Bonds: 3

Polar Surface Area: 79.53

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.47

CX Basic pKa:

CX LogP: 2.34

CX LogD: -3.93

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.77

Np Likeness Score: -0.54

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. Abet V, Mariani A, Truscott FR, Britton S, Rodriguez R..  (2014)  Biased and unbiased strategies to identify biologically active small molecules.,  22  (16): [PMID:24811300] [10.1016/j.bmc.2014.04.019]

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]

4. Gritzalis D, Park J, Chiu W, Cho H, Lin YS, De Schutter JW, Lacbay CM, Zielinski M, Berghuis AM, Tsantrizos YS..  (2015)  Probing the molecular and structural elements of ligands binding to the active site versus an allosteric pocket of the human farnesyl pyrophosphate synthase.,  25  (5): [PMID:25630225] [10.1016/j.bmcl.2014.12.089]

5. Park J, Leung CY, Matralis AN, Lacbay CM, Tsakos M, Fernandez De Troconiz G, Berghuis AM, Tsantrizos YS..  (2017)  Pharmacophore Mapping of Thienopyrimidine-Based Monophosphonate (ThP-MP) Inhibitors of the Human Farnesyl Pyrophosphate Synthase.,  60  (5): [PMID:28208018] [10.1021/acs.jmedchem.6b01888]

6. Feng Y, Park J, Li SG, Boutin R, Viereck P, Schilling MA, Berghuis AM, Tsantrizos YS..  (2019)  Chirality-Driven Mode of Binding of α-Aminophosphonic Acid-Based Allosteric Inhibitors of the Human Farnesyl Pyrophosphate Synthase (hFPPS).,  62  (21): [PMID:31577901] [10.1021/acs.jmedchem.9b01104]

Source

Source(1):

• Scientific Literature