ADP-D-Glycero-D-manno-heptose (PAMDB000960)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000960
Identification
Name: ADP-D-Glycero-D-manno-heptose
Description:ADP-D-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. ADP-L-glycero-D-manno-heptose is the lipopolysaccharide core precursor.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
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-D-β-D-heptose
  • ADP-D-b-D-Heptose
  • ADP-D-beta-D-Heptose
  • ADP-D-β-D-Heptose
Chemical Formula: C17H27N5O16P2
Average Molecular Weight: 619.3677
Monoisotopic Molecular Weight: 619.092802865
InChI Key: KMSFWBYFWSKGGR-RQWOTHMISA-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?/m1/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-[(1R)-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-[(1R)-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
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Purine nucleotides
Sub ClassPurine nucleotide sugars
Direct Parent Purine nucleotide sugars
Alternative Parents
Substituents
  • Purine nucleotide sugar
  • Purine ribonucleoside diphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.91 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity123.05 m3·mol-1ChemAxon
Polarizability52.5 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Adenosine triphosphate + D-Glycero-D-manno-heptose 1-phosphate + Hydrogen ion > ADP-D-Glycero-D-manno-heptose + Pyrophosphate
ADP-D-Glycero-D-manno-heptose <> ADP-L-Glycero-D-manno-heptose
Adenosine triphosphate + D-Glycero-D-manno-heptose 1-phosphate <> Pyrophosphate + ADP-D-Glycero-D-manno-heptose
Hydrogen ion + D-<i>glycero</i>-&beta;-D-<i>manno</i>-heptose 1-phosphate + Adenosine triphosphate > ADP-D-Glycero-D-manno-heptose + Pyrophosphate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
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 ID16693
HMDB IDNot Available
Pubchem Compound ID23724494
Kegg IDC06397
ChemSpider ID389831
Wikipedia IDNot Available
BioCyc IDADP-D-GLYCERO-D-MANNO-HEPTOSE
EcoCyc IDADP-D-GLYCERO-D-MANNO-HEPTOSE