ID: ALA432481

Max Phase: Phase

Molecular Formula: C11H11NO4S

Molecular Weight: 253.28

Molecule Type: Small molecule

Representations

Synonyms (3): Deferitrin | GT-56-252 | GT56-252
Synonyms from Alternative Forms(3):

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

Standard InChI:  InChI=1S/C11H11NO4S/c1-11(10(15)16)5-17-9(12-11)7-3-2-6(13)4-8(7)14/h2-4,13-14H,5H2,1H3,(H,15,16)/t11-/m1/s1

Standard InChI Key:  OEUUFNIKLCFNLN-LLVKDONJSA-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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 253.28

Molecular Weight (Monoisotopic): 253.0409

AlogP: 1.43

#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: 3.17

CX Basic pKa: 0.49

CX LogP: 2.50

CX LogD: -0.96

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.74

Np Likeness Score: 0.92

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, 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]

3. 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]

4. Bergeron RJ, Bharti N, Wiegand J, McManis JS, Yao H, Prokai L..  (2005)  Polyamine-vectored iron chelators: the role of charge.,  48  (12): [PMID:15943485] [10.1021/jm048974f]

5. 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]

6. 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]

7. Bergeron RJ, Wiegand J, McManis JS, Bharti N, Singh S..  (2008)  Design, synthesis, and testing of non-nephrotoxic desazadesferrithiocin polyether analogues.,  51  (13): [PMID:18533709] [10.1021/jm800154m]

8. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

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

10. Unpublished dataset, 

Source

Source(3):

• Scientific Literature
• Clinical Candidates
• USP Dictionary of USAN and International Drug Names