ChemComp-U21: uridine-5'-diphosphate-3-O-(R-3-hydroxydecanoyl)-N-acetyl-D-gluco...

Basic information

• Entry: Database: PDB chemical components / ID: U21
• Name: Name: uridine-5'-diphosphate-3-O-(R-3-hydroxydecanoyl)-N-acetyl-D-glucosamine; Synonyms: (2R,3R,4R,5S,6R)-3-(acetylamino)-2-{[(R)-{[(S)-{[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydrox

Chemical information

Composition

Formula: C₂₇H₄₅N₃O₁₉P₂ / Number of atoms: 96 / Formula weight: 777.602 / Formal charge: 0

Others

2qiv

Type: NON-POLYMER / PDB classification: HETAIN / Three letter code: U21 / Ideal coordinates details: Corina / Model coordinates PDB-ID: 2QIV

History

Create component	Jul 31, 2007
Modify descriptor	Jun 4, 2011
Modify synonyms	Jun 5, 2020

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Details

SMILES

• ACDLabs 10.04: O=P(OC1OC(C(O)C(OC(=O)CC(O)CCCCCCC)C1NC(=O)C)CO)(O)OP(=O)(O)OCC3OC(N2C=CC(=O)NC2=O)C(O)C3O
• CACTVS 3.341: CCCCCCC[CH](O)CC(=O)O[CH]1[CH](O)[CH](CO)O[CH](O[P](O)(=O)O[P](O)(=O)OC[CH]2O[CH]([CH](O)[CH]2O)N3C=CC(=O)NC3=O)[CH]1NC(C)=O
• OpenEye OEToolkits 1.5.0: CCCCCCCC(CC(=O)OC1C(C(OC(C1O)CO)OP(=O)(O)OP(=O)(O)OCC2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)NC(=O)C)O

SMILES CANONICAL

• CACTVS 3.341: CCCCCCC[C@@H](O)CC(=O)O[C@H]1[C@H](O)[C@@H](CO)O[C@H](O[P@](O)(=O)O[P@](O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=CC(=O)NC3=O)[C@@H]1NC(C)=O
• OpenEye OEToolkits 1.5.0: CCCCCCC[C@H](CC(=O)O[C@@H]1[C@H]([C@H](O[C@@H]([C@H]1O)CO)O[P@@](=O)(O)O[P@@](=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)NC(=O)C)O

InChI

• InChI 1.03: InChI=1S/C27H45N3O19P2/c1-3-4-5-6-7-8-15(33)11-19(35)47-24-20(28-14(2)32)26(46-16(12-31)22(24)37)48-51(42,43)49-50(40,41)44-13-17-21(36)23(38)25(45-17)30-10-9-18(34)29-27(30)39/h9-10,15-17,20-26,31,33,36-38H,3-8,11-13H2,1-2H3,(H,28,32)(H,40,41)(H,42,43)(H,29,34,39)/t15-,16-,17-,20-,21-,22-,23-,24-,25-,26-/m1/s1

InChIKey

• InChI 1.03: MQPZMQHQQMJGDE-MCDYFTFASA-N

SYSTEMATIC NAME

• ACDLabs 10.04: (2R,3R,4R,5S,6R)-3-(acetylamino)-2-{[(R)-{[(S)-{[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methoxy}(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl]oxy}-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl (3R)-3-hydroxydecanoate (non-preferred name)
• OpenEye OEToolkits 1.5.0: [(2R,3R,4R,5S,6R)-3-acetamido-2-[[[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl] (3R)-3-hydroxydecanoate

PDB entries

Showing all 2 items

PDB-2qiv:
Structural basis for the acyl chain selectivity and mechanism of UDP-N-acetylglucosamine acyltransferase

PDB-5dg3:
Structure of Pseudomonas aeruginosa LpxA in complex with UDP-3-O-(R-3-hydroxydecanoyl)-GlcNAc