ECMDB: ADP-L-Glycero-D-manno-heptose (ECMDB20113) (M2MDB000961)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (5)XML

Proteins (133)

Record Information

Version

2.0

Creation Date

2012-05-31 14:28:10 -0600

Update Date

2015-06-03 17:19:20 -0600

Secondary Accession Numbers

ECMDB20113

Identification

Name:

ADP-L-Glycero-D-manno-heptose

Description

ADP-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

MOL SDF PDB SMILES InChI

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.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine nucleotide sugars

Direct Parent

Purine 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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

ADP-glycero-D-manno-heptose (CHEBI:15915 )

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 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	123.05 m³·mol⁻¹	ChemAxon
Polarizability	52.45 Å³	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:

SMPDB Pathways:

Lipopolysaccharide biosynthesis

PW000831

KEGG Pathways:

Lipopolysaccharide biosynthesis ec00540
Metabolic pathways eco01100

EcoCyc Pathways:

ADP-L-glycero-β-D-manno-heptose biosynthesis PWY0-1241
Lipid A-core biosynthesis LIPA-CORESYN-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_69) - 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	15915
HMDB ID	Not Available
Pubchem Compound ID	11444938
Kegg ID	C06398
ChemSpider ID	9619800
Wikipedia ID	Not Available
BioCyc ID	ADP-L-GLYCERO-D-MANNO-HEPTOSE
EcoCyc ID	ADP-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

ADP-L-Glycero-D-manno-heptose (ECMDB20113) (M2MDB000961)

Structure for #<Compound:0xab33060c>

Enzymes

Reactions

Reactions