ID: ALA35920

Max Phase: Preclinical

Molecular Formula: C12H13NO4S

Molecular Weight: 267.31

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc(C2=N[C@@](C)(C(=O)O)CS2)c(O)c1

Standard InChI:  InChI=1S/C12H13NO4S/c1-12(11(15)16)6-18-10(13-12)8-4-3-7(17-2)5-9(8)14/h3-5,14H,6H2,1-2H3,(H,15,16)/t12-/m1/s1

Standard InChI Key:  QXLSXGGAQGTCSP-GFCCVEGCSA-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: 267.31

Molecular Weight (Monoisotopic): 267.0565

AlogP: 1.74

#Rotatable Bonds: 3

Polar Surface Area: 79.12

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.08

CX Basic pKa: 0.58

CX LogP: 2.65

CX LogD: -0.82

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.87

Np Likeness Score: 0.58

References

1. Bergeron RJ, Wiegand J, McManis JS, Bussenius J, Smith RE, Weimar WR..  (2003)  Methoxylation of desazadesferrithiocin analogues: enhanced iron clearing efficiency.,  46  (8): [PMID:12672247] [10.1021/jm020412d]

2. Bergeron RJ, Wiegand J, McManis JS, Weimar WR, Park JH, Eiler-McManis E, Bergeron J, Brittenham GM..  (2005)  Partition-variant desferrithiocin analogues: organ targeting and increased iron clearance.,  48  (3): [PMID:15689166] [10.1021/jm049306x]

3. Bergeron RJ, Wiegand J, McManis JS, Vinson JR, Yao H, Bharti N, Rocca JR..  (2006)  (S)-4,5-dihydro-2-(2-hydroxy-4-hydroxyphenyl)-4-methyl-4-thiazolecarboxylic acid polyethers: a solution to nephrotoxicity.,  49  (9): [PMID:16640338] [10.1021/jm0508944]

4. Bergeron RJ, Wiegand J, McManis JS, Bharti N..  (2006)  The design, synthesis, and evaluation of organ-specific iron chelators.,  49  (24): [PMID:17125256] [10.1021/jm0608816]

5. Bergeron RJ, Bharti N, McManis JS, Wiegand J..  (2015)  Metabolically programmed iron chelators.,  23  (17): [PMID:26231739] [10.1016/j.bmc.2015.06.059]

Source

Source(1):

• Scientific Literature