ID: ALA2164256

Max Phase: Preclinical

Molecular Formula: C12H18NO5P

Molecular Weight: 287.25

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1ccc(C(CCC(=O)N(C)O)P(=O)(O)O)cc1

Standard InChI:  InChI=1S/C12H18NO5P/c1-9-3-5-10(6-4-9)11(19(16,17)18)7-8-12(14)13(2)15/h3-6,11,15H,7-8H2,1-2H3,(H2,16,17,18)

Standard InChI Key:  YBVPWURHYFIQDS-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: 287.25

Molecular Weight (Monoisotopic): 287.0923

AlogP: 1.84

#Rotatable Bonds: 5

Polar Surface Area: 98.07

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 1.68

CX Basic pKa:

CX LogP: 0.44

CX LogD: -1.96

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.44

Np Likeness Score: -0.16

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. Konzuch S, Umeda T, Held J, Hähn S, Brücher K, Lienau C, Behrendt CT, Gräwert T, Bacher A, Illarionov B, Fischer M, Mordmüller B, Tanaka N, Kurz T..  (2014)  Binding modes of reverse fosmidomycin analogs toward the antimalarial target IspC.,  57  (21): [PMID:25254502] [10.1021/jm500850y]

Source

Source(1):

• Scientific Literature