ID: ALA11300

Max Phase: Preclinical

Molecular Formula: C10H9NO4S

Molecular Weight: 239.25

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(O)[C@H]1CSC(c2ccc(O)cc2O)=N1

Standard InChI:  InChI=1S/C10H9NO4S/c12-5-1-2-6(8(13)3-5)9-11-7(4-16-9)10(14)15/h1-3,7,12-13H,4H2,(H,14,15)/t7-/m1/s1

Standard InChI Key:  PWRDYSVMTCDMOD-SSDOTTSWSA-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: 239.25

Molecular Weight (Monoisotopic): 239.0252

AlogP: 1.04

#Rotatable Bonds: 2

Polar Surface Area: 90.12

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.10

CX Basic pKa: 0.71

CX LogP: 2.07

CX LogD: -1.40

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.72

Np Likeness Score: 1.26

References

1. Bergeron RJ, Wiegand J, Weimar WR, Vinson JR, Bussenius J, Yao GW, McManis JS..  (1999)  Desazadesmethyldesferrithiocin analogues as orally effective iron chelators.,  42  (1): [PMID:9888836] [10.1021/jm980340j]

2. 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]

3. Bergeron RJ, Huang G, Weimar WR, Smith RE, Wiegand J, McManis JS..  (2003)  Desferrithiocin analogue based hexacoordinate iron(III) chelators.,  46  (1): [PMID:12502356] [10.1021/jm020184n]

4. 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]

5. 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]

6. 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]

7. 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]

Source

Source(1):

• Scientific Literature