ChemComp-24G: uridine-5'-diphosphate-3-O-(R-3-hydroxymyristoyl)-glucosamine

Basic information

• Entry: Database: PDB chemical components / ID: 24G
• Name: Name: uridine-5'-diphosphate-3-O-(R-3-hydroxymyristoyl)-glucosamine; Synonyms: (2R,3R,4R,5S,6R)-3-amino-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-hydroxytetradecanoate

Chemical information

Composition

Formula: C₂₉H₅₁N₃O₁₈P₂ / Number of atoms: 103 / Formula weight: 791.672 / Formal charge: 0

Others

4mdt

Type: NON-POLYMER / PDB classification: HETAIN / Three letter code: 24G / Ideal coordinates details: Corina / Model coordinates PDB-ID: 4MDT

History

Create component	Aug 28, 2013
Initial release	Oct 16, 2013
Modify synonyms	Mar 13, 2021

• External links: UniChem / ChemSpider / Wikipedia search / Google search

Details

SMILES

• ACDLabs 12.01: O=C1C=CN(C(=O)N1)C2OC(C(O)C2O)COP(=O)(OP(=O)(OC3OC(C(O)C(OC(=O)CC(O)CCCCCCCCCCC)C3N)CO)O)O
• CACTVS 3.385: CCCCCCCCCCC[CH](O)CC(=O)O[CH]1[CH](N)[CH](O[CH](CO)[CH]1O)O[P](O)(=O)O[P](O)(=O)OC[CH]2O[CH]([CH](O)[CH]2O)N3C=CC(=O)NC3=O
• OpenEye OEToolkits 1.7.6: CCCCCCCCCCCC(CC(=O)OC1C(C(OC(C1O)CO)OP(=O)(O)OP(=O)(O)OCC2C(C(C(O2)N3C=CC(=O)NC3=O)O)O)N)O

SMILES CANONICAL

• CACTVS 3.385: CCCCCCCCCCC[C@@H](O)CC(=O)O[C@@H]1[C@@H](N)[C@H](O[C@H](CO)[C@H]1O)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
• OpenEye OEToolkits 1.7.6: CCCCCCCCCCC[C@H](CC(=O)O[C@@H]1[C@H]([C@H](O[C@@H]([C@H]1O)CO)OP(=O)(O)OP(=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=O)NC3=O)O)O)N)O

InChI

• InChI 1.03: InChI=1S/C29H51N3O18P2/c1-2-3-4-5-6-7-8-9-10-11-17(34)14-21(36)48-26-22(30)28(47-18(15-33)24(26)38)49-52(43,44)50-51(41,42)45-16-19-23(37)25(39)27(46-19)32-13-12-20(35)31-29(32)40/h12-13,17-19,22-28,33-34,37-39H,2-11,14-16,30H2,1H3,(H,41,42)(H,43,44)(H,31,35,40)/t17-,18-,19-,22-,23-,24-,25-,26-,27-,28-/m1/s1

InChIKey

• InChI 1.03: ZFPNNOXCEDQJQS-SSVOXRMNSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: (2R,3R,4R,5S,6R)-3-amino-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-hydroxytetradecanoate (non-preferred name)
• OpenEye OEToolkits 1.7.6: [(2R,3R,4R,5S,6R)-3-azanyl-2-[[[(2R,3S,4R,5R)-5-[2,4-bis(oxidanylidene)pyrimidin-1-yl]-3,4-bis(oxidanyl)oxolan-2-yl]methoxy-oxidanyl-phosphoryl]oxy-oxidanyl-phosphoryl]oxy-6-(hydroxymethyl)-5-oxidanyl-oxan-4-yl] (3R)-3-oxidanyltetradecanoate

PDB entries

Showing all 3 items

PDB-4mdt:
Structure of LpxC bound to the reaction product UDP-(3-O-(R-3-hydroxymyristoyl))-glucosamine

PDB-4oze:
A.aolicus LpxC in complex with native product

PDB-8v24:
LapB cytoplasmic domain in complex with LpxC