ID: ALA2164262

Max Phase: Preclinical

Molecular Formula: C10H12F2NO6P

Molecular Weight: 311.18

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN(O)C(=O)COC(c1ccc(F)c(F)c1)P(=O)(O)O

Standard InChI:  InChI=1S/C10H12F2NO6P/c1-13(15)9(14)5-19-10(20(16,17)18)6-2-3-7(11)8(12)4-6/h2-4,10,15H,5H2,1H3,(H2,16,17,18)

Standard InChI Key:  XKRWMTQGABKZDX-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: 311.18

Molecular Weight (Monoisotopic): 311.0370

AlogP: 1.01

#Rotatable Bonds: 5

Polar Surface Area: 107.30

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 1.21

CX Basic pKa:

CX LogP: -0.11

CX LogD: -2.61

Aromatic Rings: 1

Heavy Atoms: 20

QED Weighted: 0.43

Np Likeness Score: -0.91

References

1. Brücher K, Illarionov B, Held J, Tschan S, Kunfermann A, Pein MK, Bacher A, Gräwert T, Maes L, Mordmüller B, Fischer M, Kurz T..  (2012)  α-Substituted β-oxa isosteres of fosmidomycin: synthesis and biological evaluation.,  55  (14): [PMID:22731758] [10.1021/jm300652f]

2. Kunfermann A, Lienau C, Illarionov B, Held J, Gräwert T, Behrendt CT, Werner P, Hähn S, Eisenreich W, Riederer U, Mordmüller B, Bacher A, Fischer M, Groll M, Kurz T..  (2013)  IspC as target for antiinfective drug discovery: synthesis, enantiomeric separation, and structural biology of fosmidomycin thia isosters.,  56  (20): [PMID:24032981] [10.1021/jm4012559]

3. Brücher K, Gräwert T, Konzuch S, Held J, Lienau C, Behrendt C, Illarionov B, Maes L, Bacher A, Wittlin S, Mordmüller B, Fischer M, Kurz T..  (2015)  Prodrugs of reverse fosmidomycin analogues.,  58  (4): [PMID:25633870] [10.1021/jm5019719]

Source

Source(1):

• Scientific Literature