Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB006297
Identification
Name: ADP-L-glycero-beta-D-manno-heptose
Description:ADP-L-glycero-beta-D-manno-heptose is an intermediate in pathway Lipid A-core biosynthesis in Pseudomonas aeruginosa. It is a substrate for enzymes ADP-heptose:Kdo2-lipid A heptosyltransferase, ADP-heptose:LPS heptosyltransferase, lipopolysaccharide core heptosyltransferase and lipid A-core heptosyltransferase. In pathway ADP-L-glycero-beta-D-manno-heptose biosynthesis, it is a product for enzyme ADP-L-glycero-D-mannoheptose-6-epimerase which catalyzes the reaction ADP-D-glycero-beta-D-manno-heptose -> ADP-L-glycero-beta-D-manno-heptose (PMID: 11751812; BioCyc compound: ADP-L-GLYCERO-D-MANNO-HEPTOSE).
Structure
Thumb
Synonyms:
  • ADP-L-glycero-b-D-manno-Heptose
  • ADP-L-glycero-β-D-manno-Heptose
Chemical Formula: C17H25N5O16P2
Average Molecular Weight: 617.355
Monoisotopic Molecular Weight: 617.078250901
InChI Key: KMSFWBYFWSKGGR-DTBZDYEHSA-L
InChI: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-/m0/s1
CAS number: Not Available
IUPAC Name:Not Available
Traditional IUPAC Name: Not 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
Chemical Taxonomy
Taxonomy DescriptionNot Available
Kingdom Not Available
Super ClassNot Available
Class Not Available
Sub ClassNot Available
Direct Parent Not Available
Alternative Parents Not Available
Substituents Not Available
Molecular Framework Not Available
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:Not Available
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
ADP-L-glycero-Beta-D-manno-heptose biosynthesisPW002095 Pw002095Pw002095 greyscalePw002095 simple
Lipopolysaccharide biosynthesisPW000831 Pw000831Pw000831 greyscalePw000831 simple
lipopolysaccharide biosynthesis IIPW001905 Pw001905Pw001905 greyscalePw001905 simple
lipopolysaccharide biosynthesis IIIPW002059 Pw002059Pw002059 greyscalePw002059 simple
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02t9-2310009000-e08331368a76b0a7fc70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-6390078000-3fee374441206d63e4dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08or-9300000000-33b4c2d3e436e4603bb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02t9-4400009000-066591ed925c27928056View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-9310004000-713a81ebf0ff40f77b0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-9300000000-77c87b51685dad4d82e3View in MoNA
References
References: Not Available
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the interconversion between ADP-D-glycero- beta-D-manno-heptose and ADP-L-glycero-beta-D-manno-heptose via an epimerization at carbon 6 of the heptose
Gene Name:
hldD
Locus Tag:
PA3337
Molecular weight:
37.4 kDa
Reactions
ADP-D-glycero-D-manno-heptose = ADP-L-glycero-D-manno-heptose.
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Heptose transfer to the lipopolysaccharide core. It transfers the innnermost heptose to [4'-P](3-deoxy-D-manno- octulosonic acid)2-IVA
Gene Name:
rfaC
Locus Tag:
PA5011
Molecular weight:
39.7 kDa