Microbial
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2022-06-17 20:02:16 UTC
Update Date2025-10-07 16:09:17 UTC
Metabolite IDMMDBc0055688
Metabolite Identification
Common NameADP-D-glycero-beta-D-manno-heptose
DescriptionADP-D-glycero-beta-D-manno-heptose is a nucleotide sugar involved in the biosynthesis of lipopolysaccharides (LPS), classified as a carbohydrate metabolite. Its chemical structure features a heptose sugar linked to adenosine diphosphate (ADP), which plays a crucial role in various biochemical pathways. Specifically, ADP-D-glycero-beta-D-manno-heptose serves as a metabolic intermediate in the LPS biosynthetic pathway, where it is synthesized from D,D-heptose 7-phosphate through the action of specific biosynthetic enzymes, as detailed in the literature (PMID:15932222 ). This compound is recognized by the immune system; for instance, ALPK1, a protein kinase, senses ADP-D-glycero-beta-D-manno-heptose, highlighting its importance in immune responses to bacterial infections (PMID:32076438 ). Additionally, recent studies have identified ADP-D-glycero-beta-D-manno-heptose as part of a panel of predictive biomarkers, indicating its potential relevance in various physiological and pathological processes (PMID:39922 ...). The understanding of its synthesis and function continues to evolve, providing insights into its role in cellular metabolism and immune signaling.
Structure
Synonyms
ValueSource
ADP-D-Glycero-beta-D-manno-heptoseChEBI
ADP-D-Glycero-b-D-manno-heptoseGenerator
ADP-D-Glycero-β-D-manno-heptoseGenerator
ADP-D-Glycero-b-D-manno-heptose(2-)Generator
ADP-D-Glycero-β-D-manno-heptose(2-)Generator
Molecular FormulaC17H25N5O16P2
Average Mass617.355
Monoisotopic Mass617.078250901
IUPAC Name[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(2S,3S,4S,5S,6R)-6-[(1R)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl phosphono]oxy}phosphonate
Traditional Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [(2S,3S,4S,5S,6R)-6-[(1R)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl phosphono]oxyphosphonate
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(CO)[C@@]1([H])O[C@@]([H])(OP([O-])(=O)OP([O-])(=O)OC[C@@]2([H])O[C@@]([H])(N3C=NC4=C(N)N=CN=C34)[C@]([H])(O)[C@]2([H])O)[C@@]([H])(O)[C@@]([H])(O)[C@]1([H])O
InChI Identifier
InChI=1S/C17H27N5O16P2/c18-14-7-15(20-3-19-14)22(4-21-7)16-11(28)8(25)6(35-16)2-34-39(30,31)38-40(32,33)37-17-12(29)9(26)10(27)13(36-17)5(24)1-23/h3-6,8-13,16-17,23-29H,1-2H2,(H,30,31)(H,32,33)(H2,18,19,20)/p-2/t5-,6-,8-,9+,10+,11-,12+,13-,16-,17+/m1/s1
InChI KeyKMSFWBYFWSKGGR-FQBROAFUSA-L