ID: ALA2431009

Max Phase: Preclinical

Molecular Formula: C14H16NO5PS

Molecular Weight: 341.33

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN(O)C(=O)CSC(c1cccc2ccccc12)P(=O)(O)O

Standard InChI:  InChI=1S/C14H16NO5PS/c1-15(17)13(16)9-22-14(21(18,19)20)12-8-4-6-10-5-2-3-7-11(10)12/h2-8,14,17H,9H2,1H3,(H2,18,19,20)

Standard InChI Key:  RWUHAWVQQUMWLS-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: 341.33

Molecular Weight (Monoisotopic): 341.0487

AlogP: 2.60

#Rotatable Bonds: 5

Polar Surface Area: 98.07

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 1.50

CX Basic pKa:

CX LogP: 1.00

CX LogD: -1.43

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.44

Np Likeness Score: -0.48

References

1. 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]

2. Lienau C, Gräwert T, Alves Avelar LA, Illarionov B, Held J, Knaab TC, Lungerich B, van Geelen L, Meier D, Geissler S, Cynis H, Riederer U, Buchholz M, Kalscheuer R, Bacher A, Mordmüller B, Fischer M, Kurz T..  (2019)  Novel reverse thia-analogs of fosmidomycin: Synthesis and antiplasmodial activity.,  181  [PMID:31382119] [10.1016/j.ejmech.2019.07.058]

Source

Source(1):

• Scientific Literature