Bovine Metabolome Database: Showing metabocard for Guanosine diphosphate mannose (BMDB0001163)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:41:50 UTC

Update Date

2020-05-21 16:26:57 UTC

BMDB ID

BMDB0001163

Secondary Accession Numbers

BMDB01163

Metabolite Identification

Common Name

Guanosine diphosphate mannose

Description

Guanosine diphosphate mannose, also known as guanosine diphosphate mannose or guanosine diphosphate mannose, 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. Guanosine diphosphate mannose is possibly soluble (in water) and a strong basic compound (based on its pKa). Guanosine diphosphate mannose exists in all living species, ranging from bacteria to humans. Guanosine diphosphate mannose participates in a number of enzymatic reactions, within cattle. In particular, Guanosine diphosphate mannose can be biosynthesized from D-mannose 1-phosphate; which is catalyzed by the enzyme mannose-1-phosphate guanyltransferase beta. In addition, Guanosine diphosphate mannose can be converted into GDP-4-dehydro-6-deoxy-D-mannose; which is mediated by the enzyme GDP-mannose 4,6 dehydratase. In cattle, guanosine diphosphate mannose is involved in the metabolic pathway called the fructose and mannose degradation pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
GDP-D-Mannose	ChEBI
GDPmannose	ChEBI
Guanosine 5'-(trihydrogen diphosphate), mono-alpha-D-mannopyranosyl ester	ChEBI
Guanosine diphosphomannose	ChEBI
Guanosine pyrophosphate mannose	ChEBI
GDP-alpha-D-Mannose	Kegg
Guanosine 5'-(trihydrogen diphosphate), mono-a-D-mannopyranosyl ester	Generator
Guanosine 5'-(trihydrogen diphosphate), mono-α-D-mannopyranosyl ester	Generator
Guanosine 5'-(trihydrogen diphosphoric acid), mono-a-D-mannopyranosyl ester	Generator
Guanosine 5'-(trihydrogen diphosphoric acid), mono-alpha-D-mannopyranosyl ester	Generator
Guanosine 5'-(trihydrogen diphosphoric acid), mono-α-D-mannopyranosyl ester	Generator
Guanosine pyrophosphoric acid mannose	Generator
GDP-a-D-Mannose	Generator
GDP-Α-D-mannose	Generator
Guanosine diphosphoric acid mannose	Generator
GDP Mannose	HMDB
GDP-Glucose	HMDB
GDP-Mannose	HMDB
Pyrophosphate mannose, guanosine	HMDB
Diphosphomannose, guanosine	HMDB
Mannose, guanosine diphosphate	HMDB
Diphosphate mannose, guanosine	HMDB
Mannose, guanosine pyrophosphate	HMDB
Mannose, GDP	HMDB
Guanosine 5'-(trihydrogen diphosphate) p'-mannosyl ester	HMDB
Guanosine 5'-(trihydrogen pyrophosphate) mono-D-mannosyl ester	HMDB
Guanosine 5'-(trihydrogen pyrophosphate) monomannopyranosyl ester	HMDB
Guanosine 5'-(trihydrogen pyrophosphate) monomannosyl ester	HMDB
Guanosine 5'-diphosphate D-mannose	HMDB
Guanosine 5'-pyrophosphate D-mannosyl ester	HMDB
Guanosine 5'-pyrophosphate alpha-D-mannosyl ester	HMDB
Guanosine 5'-pyrophosphate α-D-mannosyl ester	HMDB
Guanosine 5’-(trihydrogen diphosphate) p’-mannosyl ester	HMDB
Guanosine 5’-(trihydrogen pyrophosphate) mono-D-mannosyl ester	HMDB
Guanosine 5’-(trihydrogen pyrophosphate) monomannopyranosyl ester	HMDB
Guanosine 5’-(trihydrogen pyrophosphate) monomannosyl ester	HMDB
Guanosine 5’-diphosphate D-mannose	HMDB
Guanosine 5’-pyrophosphate D-mannosyl ester	HMDB
Guanosine 5’-pyrophosphate α-D-mannosyl ester	HMDB
Guanosine diphosphate mannose	HMDB

Chemical Formula

C₁₆H₂₅N₅O₁₆P₂

Average Molecular Weight

605.3411

Monoisotopic Molecular Weight

605.077152801

IUPAC Name

[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

Traditional Name

guanosine diphosphomannose

CAS Registry Number

3123-67-9

SMILES

NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H](O)[C@H]2O)C(=O)N1

InChI Identifier

InChI=1S/C16H25N5O16P2/c17-16-19-12-6(13(28)20-16)18-3-21(12)14-10(26)8(24)5(34-14)2-33-38(29,30)37-39(31,32)36-15-11(27)9(25)7(23)4(1-22)35-15/h3-5,7-11,14-15,22-27H,1-2H2,(H,29,30)(H,31,32)(H3,17,19,20,28)/t4-,5-,7-,8-,9+,10-,11+,14-,15-/m1/s1

InChI Key

MVMSCBBUIHUTGJ-GDJBGNAASA-N

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
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Hydroxypyrimidine
Monoalkyl phosphate
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Pyrimidine
Heteroaromatic compound
Tetrahydrofuran
Imidazole
Azole
Secondary alcohol
Polyol
Oxacycle
Organoheterocyclic compound
Azacycle
Organic oxygen compound
Alcohol
Organic oxide
Primary alcohol
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

GDP-D-mannose (CHEBI:15820 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.8	ALOGPS
logP	-5.3	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	327.43 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	118.51 m³·mol⁻¹	ChemAxon
Polarizability	48.72 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-05bu-5842490000-d73f755e03b8ad234b29	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-01r6-7882509000-02adbc06a0f79e803d88	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 32V, positive	splash10-0a4i-0000209000-fa2b35ba4f2fbdff74a3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 32V, negative	splash10-0udi-3401309000-93213e14894fde4ba5c2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0001309000-586a7f020650fe518e5f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0900000000-bba5489b865ff8d5ba78	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0100900000-d5b51af9c9e096503197	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900400000-3410bfae1c82b5e08999	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00b9-9434300000-661dad8f3e9cd9b10a38	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000009000-c84788b57e1d68c3a299	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0910510000-30a5518df6f0f53ad7b7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0910000000-48aef418f3aa94cc35f8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-1900000000-438261daf883fac47d6c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-1901325000-e5d0bcd5db4a59b606f8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1901100000-a8c00836fd0ca5a71ad1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pdl-3900000000-358726d071759c859d9e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000009000-3f663b5fce4f431e1e25	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-4701986000-bb5e3a66be23d7de55e6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05i0-3911810000-ee275d8a12bcf1e5065c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900002000-37d2f661727ecc1c915a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900001000-de8f3c7c7e6a620f0e90	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udr-2930000000-7a0fc600f843201b86c4	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Fructose and Mannose Degradation		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0001163

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Guanosine diphosphate mannose

METLIN ID

6045

PubChem Compound

18396

PDB ID

Not Available

ChEBI ID

15820

References

Synthesis Reference

Huang, Gang-Liang; Liu, Xiang; Zhang, Hou-Cheng; Wang, Peng-George. A facile two-step chemo-enzymatic synthesis of GDP-mannose. Letters in Organic Chemistry (2006), 3(9), 668-669.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. dTDP-D-glucose 4,6-dehydratase

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Not Available
Gene Name:: TGDS
Uniprot ID:: A6QLW2
Molecular weight:: 40666.0

Reactions

Guanosine diphosphate mannose → GDP-4-Dehydro-6-deoxy-D-mannose + Water	details

Enzyme Details

2. Dolichol-phosphate mannosyltransferase subunit 1

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Transfers mannose from GDP-mannose to dolichol monophosphate to form dolichol phosphate mannose (Dol-P-Man) which is the mannosyl donor in pathways leading to N-glycosylation, glycosyl phosphatidylinositol membrane anchoring, and O-mannosylation of proteins; catalytic subunit of the dolichol-phosphate mannose (DPM) synthase complex.
Gene Name:: DPM1
Uniprot ID:: Q1JQ93
Molecular weight:: 29592.0

Enzyme Details

3. Mannose-1-phosphate guanyltransferase beta

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Catalyzes the formation of GDP-mannose, an essential precursor of glycan moieties of glycoproteins and glycolipids.
Gene Name:: GMPPB
Uniprot ID:: Q2YDJ9
Molecular weight:: 39837.0

Reactions

Guanosine triphosphate + D-Mannose 1-phosphate → Guanosine diphosphate mannose + Pyrophosphate	details

Showing metabocard for Guanosine diphosphate mannose (BMDB0001163)

Structure for BMDB0001163 (Guanosine diphosphate mannose)

Enzymes

Reactions

Reactions