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Record Information
Version	2.0
Creation Date	2012-05-31 14:28:07 -0600
Update Date	2015-06-03 17:19:20 -0600
Secondary Accession Numbers	ECMDB20112
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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xacaf99f0> Close
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
Weight:	Average: 619.3677 Monoisotopic: 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
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.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Purine nucleotides
Sub Class	Purine nucleotide sugars
Direct Parent	Purine nucleotide sugars
Alternative Parents	Purine ribonucleoside diphosphates Purine ribonucleoside monophosphates Pentose phosphates Glycosylamines 6-aminopurines Organic pyrophosphates Monosaccharide phosphates Aminopyrimidines and derivatives Monoalkyl phosphates Oxanes Imidolactams N-substituted imidazoles Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Azacyclic compounds Polyols Oxacyclic compounds Primary amines Primary alcohols Hydrocarbon derivatives Organopnictogen compounds Organic oxides
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 Framework	Aromatic heteropolycyclic compounds
External Descriptors	ADP-glycero-D-manno-heptose (CHEBI:16693 )
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 5.91 g/L ALOGPS logP -1.8 ALOGPS logP -8 ChemAxon logS -2 ALOGPS pKa (Strongest Acidic) 1.73 ChemAxon pKa (Strongest Basic) 5 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 17 ChemAxon Hydrogen Donor Count 10 ChemAxon Polar Surface Area 331.98 Ų ChemAxon Rotatable Bond Count 10 ChemAxon Refractivity 123.05 m³·mol⁻¹ ChemAxon Polarizability 52.5 ų ChemAxon Number of Rings 4 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
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 ADP-D-Glycero-D-manno-heptose > ADP-L-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 D-glycero-beta-D-manno-heptose 1-phosphate + Adenosine triphosphate + Hydrogen ion > ADP-D-Glycero-D-manno-heptose + Pyrophosphate ADP-D-Glycero-D-manno-heptose > ADP-L-glycero-beta-D-manno-heptose ADP-D-Glycero-D-manno-heptose <> ADP-L-Glycero-D-manno-heptose 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 + Hydrogen ion > ADP-D-Glycero-D-manno-heptose + Pyrophosphate
SMPDB Pathways:	ADP-L-glycero-Beta-D-manno-heptose biosynthesis PW002095 Lipopolysaccharide biosynthesis PW000831
KEGG Pathways:	Lipopolysaccharide biosynthesis ec00540 Metabolic pathways eco01100
EcoCyc Pathways:	ADP-L-glycero-β-D-manno-heptose biosynthesis PWY0-1241
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_3_48) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-000i-0910502000-8c3562506ded6f437c8a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-000i-0910000000-2624f0a80c52e6957690 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-000i-2900000000-bede1fb56b90862d8f7f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0api-4901245000-42682d865153e9fc153e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001i-2901000000-baf9b8dcb69cf8da70fe View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0563-3900000000-135806b9f5fcb9949d51 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View 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
Links
External Links:	Resource Link CHEBI ID 16693 HMDB ID Not Available Pubchem Compound ID 23724494 Kegg ID C06397 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID ADP-D-GLYCERO-D-MANNO-HEPTOSE EcoCyc ID ADP-D-GLYCERO-D-MANNO-HEPTOSE

Enzymes