ID: ALA2347863

Max Phase: Preclinical

Molecular Formula: C17H15N3O6P2S

Molecular Weight: 451.34

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=P(O)(O)C(Nc1ncnc2sc(-c3ccc4ccccc4c3)cc12)P(=O)(O)O

Standard InChI:  InChI=1S/C17H15N3O6P2S/c21-27(22,23)17(28(24,25)26)20-15-13-8-14(29-16(13)19-9-18-15)12-6-5-10-3-1-2-4-11(10)7-12/h1-9,17H,(H,18,19,20)(H2,21,22,23)(H2,24,25,26)

Standard InChI Key:  AHKZPDVODREWAP-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: 451.34

Molecular Weight (Monoisotopic): 451.0157

AlogP: 3.56

#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: 3.82

CX LogP: 0.49

CX LogD: -2.37

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.29

Np Likeness Score: -0.91

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]

Source

Source(1):

• Scientific Literature