Details of the Drug

General Information of Drug (ID: DMEQSTP)

Drug Name

Uridine-Diphosphate-N-Acetylglucosamine

Synonyms

UDP-N-acetylglucosamine; UDP-GlcNAc; UDP-N-acetyl-D-glucosamine; URIDINE-DIPHOSPHATE-N-ACETYLGLUCOSAMINE; UPPAG; UDP-acetylglucosamine; uridine diphosphate N-acetylglucosamine; UDP-N-acetyl-alpha-D-glucosamine; Uridine diphosphate-N-acetylglucosamine; 528-04-1; UDP-acetyl-D-glucosamine; Uridine diphospho-N-acetylglucosamine; Uridine 5'-diphospho-N-acetylglucosamine; [(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxy

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 4

Molecular Weight (mw)

607.4

Topological Polar Surface Area (xlogp)

-6.6

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C17H27N3O17P2
IUPAC Name: [(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl] [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate
Canonical SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OP(=O)(O)OP(=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)CO)O)O
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
InChIKey: LFTYTUAZOPRMMI-CFRASDGPSA-N

Cross-matching ID

PubChem CID: 445675
ChEBI ID: CHEBI:16264
CAS Number: 528-04-1
DrugBank ID: DB03397
TTD ID: D0KC2Z

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial UDP-N-acetylglucosamine carboxyvinyltransferase (Bact murA)	TTICX3S	MURA_ECOLI	Inhibitor	[2]
UDP-glucose 4-epimerase (GALE)	TTGRHIB	GALE_HUMAN	Inhibitor	[2]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 1779).
2	DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Nucleic Acids Res. 2011 Jan;39(Database issue):D1035-41.
3	Evidence that the fosfomycin target Cys115 in UDP-N-acetylglucosamine enolpyruvyl transferase (MurA) is essential for product release. J Biol Chem. 2005 Feb 4;280(5):3757-63.
4	Emerging drugs for bacterial urinary tract infections. Expert Opin Emerg Drugs. 2005 May;10(2):275-98.
5	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
6	Sesquiterpene lactones are potent and irreversible inhibitors of the antibacterial target enzyme MurA. Bioorg Med Chem Lett. 2006 Nov 1;16(21):5605-9.
7	Identification of novel inhibitors of UDP-Glc 4'-epimerase, a validated drug target for african sleeping sickness. Bioorg Med Chem Lett. 2006 Nov 15;16(22):5744-7.
8	Crystal structure of beta1,4-galactosyltransferase complex with UDP-Gal reveals an oligosaccharide acceptor binding site. J Mol Biol. 2002 Apr 26;318(2):491-502.