UDP N-acetyl-glucosamine   Click here for help

GtoPdb Ligand ID: 1779

Synonyms: UDP-acetylglucosamine | UPPAG | uridine diphosphate N-acetylglucosamine
PDB Ligand
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 18
Hydrogen bond donors 9
Rotatable bonds 11
Topological polar surface area 325.48
Molecular weight 607.08
XLogP -5.21
No. Lipinski's rules broken 2
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Canonical SMILES OCC1OC(OP(=O)(OP(=O)(OCC2OC(C(C2O)O)n2ccc(=O)[nH]c2=O)O)O)C(C(C1O)O)NC(=O)C
Isomeric SMILES OC[C@H]1O[C@H](OP(=O)(OP(=O)(OC[C@H]2O[C@H]([C@@H]([C@@H]2O)O)n2ccc(=O)[nH]c2=O)O)O)[C@@H]([C@H]([C@@H]1O)O)NC(=O)C
InChI InChI=1S/C17H27N3O17P2/c1-6(22)18-10-13(26)11(24)7(4-21)35-16(10)36-39(31,32)37-38(29,30)33-5-8-12(25)14(27)15(34-8)20-3-2-9(23)19-17(20)28/h2-3,7-8,10-16,21,24-27H,4-5H2,1H3,(H,18,22)(H,29,30)(H,31,32)(H,19,23,28)/t7-,8-,10-,11-,12-,13-,14-,15-,16-/m1/s1
1. Ashikov A, Routier F, Fuhlrott J, Helmus Y, Wild M, Gerardy-Schahn R, Bakker H. (2005)
The human solute carrier gene SLC35B4 encodes a bifunctional nucleotide sugar transporter with specificity for UDP-xylose and UDP-N-acetylglucosamine.
J Biol Chem, 280 (29): 27230-5. [PMID:15911612]
2. Freeman K, Tsui P, Moore D, Emson PC, Vawter L, Naheed S, Lane P, Bawagan H, Herrity N, Murphy K et al.. (2001)
Cloning, pharmacology, and tissue distribution of G-protein-coupled receptor GPR105 (KIAA0001) rodent orthologs.
Genomics, 78 (3): 124-8. [PMID:11735218]
3. Fricks IP, Carter RL, Lazarowski ER, Harden TK. (2009)
Gi-dependent cell signaling responses of the human P2Y14 receptor in model cell systems.
J Pharmacol Exp Ther, 330 (1): 162-8. [PMID:19339661]
4. Ishida N, Miura N, Yoshioka S, Kawakita M. (1996)
Molecular cloning and characterization of a novel isoform of the human UDP-galactose transporter, and of related complementary DNAs belonging to the nucleotide-sugar transporter gene family.
J Biochem, 120 (6): 1074-8. [PMID:9010752]
5. Ishida N, Yoshioka S, Chiba Y, Takeuchi M, Kawakita M. (1999)
Molecular cloning and functional expression of the human Golgi UDP-N-acetylglucosamine transporter.
J Biochem, 126 (1): 68-77. [PMID:10393322]
6. Miura N, Ishida N, Hoshino M, Yamauchi M, Hara T, Ayusawa D, Kawakita M. (1996)
Human UDP-galactose translocator: molecular cloning of a complementary DNA that complements the genetic defect of a mutant cell line deficient in UDP-galactose translocator.
J Biochem, 120 (2): 236-41. [PMID:8889805]