ID: ALA79962

Max Phase: Preclinical

Molecular Formula: C10H9NO3S

Molecular Weight: 223.25

Molecule Type: Small molecule

Representations

Synonyms (1): (+)-(R)-Dihydroaeruginoic Acid
Synonyms from Alternative Forms(1):

Canonical SMILES:  O=C(O)[C@@H]1CSC(c2ccccc2O)=N1

Standard InChI:  InChI=1S/C10H9NO3S/c12-8-4-2-1-3-6(8)9-11-7(5-15-9)10(13)14/h1-4,7,12H,5H2,(H,13,14)/t7-/m0/s1

Standard InChI Key:  CECDPVOEINSAQG-ZETCQYMHSA-N

Molecule Features

Natural Product: Yes

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: 223.25

Molecular Weight (Monoisotopic): 223.0303

AlogP: 1.34

#Rotatable Bonds: 2

Polar Surface Area: 69.89

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.36

CX Basic pKa: 0.87

CX LogP: 2.37

CX LogD: -1.04

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.79

Np Likeness Score: 0.93

References

1. Bergeron RJ, Wiegand J, McManis JS, McCosar BH, Weimar WR, Brittenham GM, Smith RE..  (1999)  Effects of C-4 stereochemistry and C-4' hydroxylation on the iron clearing efficiency and toxicity of desferrithiocin analogues.,  42  (13): [PMID:10395484] [10.1021/jm990058s]

2. Bergeron RJ, Wollenweber M, Wiegand J..  (1994)  An investigation of desferrithiocin metabolism.,  37  (18): [PMID:8071936] [10.1021/jm00044a009]

3. Carmi R, Carmeli S, Levy E, Gough FJ..  (1994)  (+)-(S)-dihydroaeruginoic acid, an inhibitor of Septoria tritici and other phytopathogenic fungi and bacteria, produced by Pseudomonas fluorescens.,  57  (9): [PMID:7798954] [10.1021/np50111a002]

4. Chen P, Horton LB, Mikulski RL, Deng L, Sundriyal S, Palzkill T, Song Y..  (2012)  2-Substituted 4,5-dihydrothiazole-4-carboxylic acids are novel inhibitors of metallo-β-lactamases.,  22  (19): [PMID:22921080] [10.1016/j.bmcl.2012.08.012]

Source

Source(1):

• Scientific Literature