dehydroascorbic acid   

GtoPdb Ligand ID: 4733

Synonyms: dehydroascorbate
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 100.9
Molecular weight 174.02
XLogP -1.88
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES OCC(C1OC(=O)C(=O)C1=O)O
Isomeric SMILES OC[C@@H]([C@H]1OC(=O)C(=O)C1=O)O
InChI InChI=1S/C6H6O6/c7-1-2(8)5-3(9)4(10)6(11)12-5/h2,5,7-8H,1H2/t2-,5+/m0/s1
InChI Key SBJKKFFYIZUCET-JLAZNSOCSA-N
References
1. Bianchi J, Rose RC. (1986)
Glucose-independent transport of dehydroascorbic acid in human erythrocytes.
Proc. Soc. Exp. Biol. Med., 181 (3): 333-7. [PMID:3945643]
2. Lee YC, Huang HY, Chang CJ, Cheng CH, Chen YT. (2010)
Mitochondrial GLUT10 facilitates dehydroascorbic acid import and protects cells against oxidative stress: mechanistic insight into arterial tortuosity syndrome.
Hum. Mol. Genet., 19 (19): 3721-33. [PMID:20639396]
3. Tsukaguchi H, Tokui T, Mackenzie B, Berger UV, Chen XZ, Wang Y, Brubaker RF, Hediger MA. (1999)
A family of mammalian Na+-dependent L-ascorbic acid transporters.
Nature, 399 (6731): 70-5. [PMID:10331392]