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ADP-L-Glycero-D-manno-heptose (M2MDB000961)

Record Information
Version2.0
Creation Date2012-05-31 14:28:10 -0600
Update Date2015-06-03 17:19:20 -0600
Secondary Accession Numbers
  • ECMDB20113
Identification
Name:ADP-L-Glycero-D-manno-heptose
DescriptionADP-L-glycero-D-manno-heptose is a member of the chemical class known as Purine Nucleotide Sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. Functional analysis of the glycero-manno-heptose 7-phosphate kinase domain from the bifunctional HldE protein, which is involved in ADP-L-glycero-D-manno-heptose biosynthesis. (PMID 16030223)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-[[[5-[(6-Amino-9H-purin-9-yl)]-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphinoyl]oxy-hydroxy-phosphinoyl]oxy-6-(1,2-dihydroxyethyl)tetrahydropyran-3,4,5-triol
  • ADP-L-glycero-D-manno-heptose
Chemical Formula:C17H27N5O16P2
Weight:Average: 619.3677
Monoisotopic: 619.092802865
InChI Key:KMSFWBYFWSKGGR-XRLZOAFQSA-N
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)/t5-,6+,8+,9-,10-,11+,12-,13+,16+,17?/m0/s1
CAS number:Not Available
IUPAC Name:[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3S,4S,5S,6R)-6-[(1S)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl]oxy})phosphinic acid
Traditional IUPAC Name:{[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy[(3S,4S,5S,6R)-6-[(1S)-1,2-dihydroxyethyl]-3,4,5-trihydroxyoxan-2-yl]oxyphosphinic acid
SMILES:[H][C@](O)(CO)[C@@]1([H])OC([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
Description belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine nucleotide sugars
Direct ParentPurine nucleotide sugars
Alternative Parents
Substituents
  • Purine nucleotide sugar
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Polyol
  • Oxacycle
  • Organic oxide
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Amine
  • Organonitrogen compound
  • Primary alcohol
  • Primary amine
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.91 g/LALOGPS
logP-1.8ALOGPS
logP-8ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area331.98 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity123.05 m³·mol⁻¹ChemAxon
Polarizability52.45 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
ADP-D-Glycero-D-manno-heptose <> ADP-L-Glycero-D-manno-heptose
ADP-L-Glycero-D-manno-heptose + heptosyl-kdo2-lipidA > ADP + Hydrogen ion + heptosyl-heptosyl-kdo2-lipidA
ADP-L-Glycero-D-manno-heptose + KDO2-Lipid A > ADP + Hydrogen ion + heptosyl-kdo2-lipidA
ADP-L-Glycero-D-manno-heptose + glucosyl-glucosyl-galactosyl-glucosyl-inner core oligosaccharide lipid A > ADP + core oligosaccharide lipid A + Hydrogen ion
ADP-L-Glycero-D-manno-heptose + Phospho-heptosyl-heptosyl-kdo2-lipidA > ADP + Hydrogen ion + Heptosyl-phospho-heptosyl-heptosyl-kdo2-lipidA
&alpha;-Kdo-(2->4)-&alpha;-Kdo-(2->6)-lipid IV<SUB>A</SUB> + ADP-L-Glycero-D-manno-heptose Hydrogen ion + heptosyl-Kdo<sub>2</sub>-lipid IV<sub>A</sub> + ADP
ADP-D-Glycero-D-manno-heptose > ADP-L-Glycero-D-manno-heptose
Heptosyl-KDO2-lipid A + ADP-L-Glycero-D-manno-heptose > Hydrogen ion + Heptosyl2-KDO2-lipid A + ADP
Hydrogen ion + KDO2-Lipid A + ADP-L-Glycero-D-manno-heptose > Heptosyl-KDO2-lipid A + ADP
Glucosyl-heptosyl2-KDO2-lipid A-phosphate + ADP-L-Glycero-D-manno-heptose > Hydrogen ion + Glucosyl-heptosyl3-KDO2-lipid A-phosphate + ADP
Galactosyl-glucosyl3-heptosyl3-KDO2-lipid A-bisphosphate + ADP-L-Glycero-D-manno-heptose > Hydrogen ion + Lipid A-core + ADP
ADP-D-Glycero-D-manno-heptose <> ADP-L-Glycero-D-manno-heptose
ADP-D-Glycero-D-manno-heptose <> ADP-L-Glycero-D-manno-heptose
SMPDB Pathways:
Lipopolysaccharide biosynthesisPW000831 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_3_69) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0910502000-8c3562506ded6f437c8aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0910000000-2624f0a80c52e6957690View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-bede1fb56b90862d8f7fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0api-4901245000-42682d865153e9fc153eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2901000000-baf9b8dcb69cf8da70feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0563-3900000000-135806b9f5fcb9949d51View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15915
HMDB IDNot Available
Pubchem Compound ID11444938
Kegg IDC06398
ChemSpider ID9619800
Wikipedia IDNot Available
BioCyc IDADP-L-GLYCERO-D-MANNO-HEPTOSE
EcoCyc IDADP-L-GLYCERO-D-MANNO-HEPTOSE

Enzymes

Protein Details
1. ADP-L-glycero-D-manno-heptose-6-epimerase
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
Uniprot ID:
P67910
Molecular weight:
34893
Reactions
ADP-D-glycero-D-manno-heptose = ADP-L-glycero-D-manno-heptose.
Protein Details
2. Lipopolysaccharide core heptosyltransferase rfaQ
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Catalyzes heptose transfer to the lipopolysaccharide core. It transfers a heptose, called heptose(III), to the heptose(II) of the inner core
Gene Name:
rfaQ
Uniprot ID:
P25742
Molecular weight:
38730
Protein Details
3. Lipopolysaccharide 1,2-N-acetylglucosaminetransferase
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Adds the terminal N-acetyl-D-glucosamine group on the glucose(II) group of LPS
Gene Name:
waaU
Uniprot ID:
P27242
Molecular weight:
41729
Reactions
UDP-N-acetyl-D-glucosamine + lipopolysaccharide = UDP + N-acetyl-D-glucosaminyllipopolysaccharide.
Protein Details
4. ADP-heptose--LPS heptosyltransferase 2
General function:
Involved in transferase activity, transferring glycosyl groups
Specific function:
Specific function unknown
Gene Name:
rfaF
Uniprot ID:
P37692
Molecular weight:
39042
Protein Details
5. Lipopolysaccharide heptosyltransferase 1
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
Uniprot ID:
P24173
Molecular weight:
35544