Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:10:05 UTC
HMDB IDHMDB01201
Secondary Accession NumbersNone
Metabolite Identification
Common NameGuanosine diphosphate
DescriptionGuanosine 5'-(trihydrogen diphosphate). A guanine nucleotide containing two phosphate groups esterified to the sugar moiety. It is an ester of pyrophosphoric acid with the nucleoside guanosine. GDP consists of the pyrophosphate group, the pentose sugar ribose, and the nucleobase guanine. GDP is the product of GTP dephosphorylation by GTPases, e.g. the G-proteins that are involved in signal transduction.
Structure
Thumb
Synonyms
  1. 5'-GDP
  2. GDP
  3. Guanosine 5'-(trihydrogen pyrophosphate)
  4. Guanosine 5'-diphosphate
  5. Guanosine 5'-pyrophosphate
  6. Guanosine mono(trihydrogen diphosphate)
  7. Guanosine pyrophosphate
  8. Guanosine-5'-diphosphate
  9. Guanosine-diphosphate
  10. PpG
Chemical FormulaC10H15N5O11P2
Average Molecular Weight443.2005
Monoisotopic Molecular Weight443.024329371
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]phosphonic acid
Traditional IUPAC Name{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxyphosphonic acid
CAS Registry Number146-91-8
SMILES
NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1
InChI Identifier
InChI=1S/C10H15N5O11P2/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(25-9)1-24-28(22,23)26-27(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1
InChI KeyQGWNDRXFNXRZMB-UUOKFMHZSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassNucleosides, Nucleotides, and Analogues
ClassPurine Nucleotides
Sub ClassPurine Ribonucleotides
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • Ribonucleotides(KEGG)
  • guanosine 5'-phosphate(ChEBI)
  • purine ribonucleoside 5'-diphosphate(ChEBI)
Substituents
  • 1,2 Diol
  • 1 Phosphoribosyl Imidazole
  • Aminopyrimidine
  • Glycosyl Compound
  • Hypoxanthine
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Purinone
  • Pyrimidine
  • Pyrimidone
  • Saccharide
  • Secondary Alcohol
Direct ParentPurine Ribonucleoside Diphosphates
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Fructose and mannose metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Nucleus
  • Golgi apparatus
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility4.44 g/LALOGPS
logP-1.5ALOGPS
logP-3.5ChemAxon
logS-2ALOGPS
pKa (strongest acidic)1.97ChemAxon
pKa (strongest basic)1.35ChemAxon
physiological charge-2ChemAxon
hydrogen acceptor count12ChemAxon
hydrogen donor count7ChemAxon
polar surface area248.28ChemAxon
rotatable bond count6ChemAxon
refractivity86.37ChemAxon
polarizability35.28ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondria
  • Nucleus
  • Golgi apparatus
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Citric Acid CycleSMP00057map00020
GluconeogenesisSMP00128map00010
Purine MetabolismSMP00050map00230
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified15.0 +/- 2.0 uMAdult (>18 years old)MaleNormal
  • Geigy Scient...
BloodDetected and Quantified18.0 +/- 8.0 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified1.86 +/- 0.027 uMAdult (>18 years old)BothNormal
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
Cerebrospinal Fluid (CSF)Detected and Quantified2.11 +/- 1.93 uMAdult (>18 years old)BothRachialgia
Cerebrospinal Fluid (CSF)Detected and Quantified4.05 +/- 0.03 uMAdult (>18 years old)BothSubarachnoid hemorrhage
Cerebrospinal Fluid (CSF)Detected and Quantified0.99 +/- 1.32 uMAdult (>18 years old)BothEpilepsy
Cerebrospinal Fluid (CSF)Detected and Quantified2.55 +/- 1.62 uMAdult (>18 years old)BothCommentStroke
Cerebrospinal Fluid (CSF)Detected and Quantified2.59 +/- 1.77 uMAdult (>18 years old)BothNeuroinfection
Associated Disorders and Diseases
Disease References
Subarachnoid hemorrhage
  • Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. Pubmed: 15993662
Epilepsy
  • Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. Pubmed: 15993662
Neuroinfection
  • Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. Pubmed: 15993662
Rachialgia
  • Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. Pubmed: 15993662
Stroke
  • Czarnecka J, Cieslak M, Michal K: Application of solid phase extraction and high-performance liquid chromatography to qualitative and quantitative analysis of nucleotides and nucleosides in human cerebrospinal fluid. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 5;822(1-2):85-90. Pubmed: 15993662
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022487
KNApSAcK IDNot Available
Chemspider ID8630
KEGG Compound IDC00035
BioCyc IDGDP-4-DEHYDRO-6-DEOXY-D-MANNOSE
BiGG ID33599
Wikipedia LinkGDP
NuGOwiki LinkHMDB01201
Metagene LinkHMDB01201
METLIN ID6077
PubChem Compound8977
PDB IDGDP
ChEBI ID17552
References
Synthesis ReferenceEdlin, Gordon; Donini, P. Synthesis of guanosine 5'-diphosphate, 2'-(or 3'-) diphosphate, and related nucleotides in a variety of physiological conditions. Journal of Biological Chemistry (1971), 246(13), 4371-3.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chantin C, Bonin B, Boulieu R, Bory C: Liquid-chromatographic study of purine metabolism abnormalities in purine nucleoside phosphorylase deficiency. Clin Chem. 1996 Feb;42(2):326-8. Pubmed: 8595732

Only showing the first 50 proteins. There are 230 proteins in total.

Enzymes

Gene Name:
ENTPD1
Uniprot ID:
P49961
Reactions
Guanosine diphosphate + Water unknown Guanosine monophosphate + Phosphoric aciddetails
Guanosine triphosphate + Water unknown Guanosine diphosphate + Phosphoric aciddetails
Gene Name:
CANT1
Uniprot ID:
Q8WVQ1
Reactions
Guanosine diphosphate + Water unknown Guanosine monophosphate + Phosphoric aciddetails
Gene Name:
ENTPD3
Uniprot ID:
O75355
Reactions
Guanosine diphosphate + Water unknown Guanosine monophosphate + Phosphoric aciddetails
Guanosine triphosphate + Water unknown Guanosine diphosphate + Phosphoric aciddetails
Gene Name:
UCK1
Uniprot ID:
Q9HA47
Reactions
Guanosine triphosphate + Cytidine unknown Guanosine diphosphate + Cytidine monophosphatedetails
Guanosine triphosphate + Uridine unknown Guanosine diphosphate + Uridine 5'-monophosphatedetails
Gene Name:
NME4
Uniprot ID:
O00746
Reactions
Adenosine triphosphate + Guanosine diphosphate unknown ADP + Guanosine triphosphatedetails
Gene Name:
RRM1
Uniprot ID:
P23921
Reactions
dGDP + Thioredoxin disulfide + Water unknown Guanosine diphosphate + Thioredoxindetails
Gene Name:
NME1
Uniprot ID:
P15531
Reactions
Adenosine triphosphate + Guanosine diphosphate unknown ADP + Guanosine triphosphatedetails
Gene Name:
NME7
Uniprot ID:
Q9Y5B8
Reactions
Adenosine triphosphate + Guanosine diphosphate unknown ADP + Guanosine triphosphatedetails
Gene Name:
RRM2
Uniprot ID:
P31350
Reactions
dGDP + Thioredoxin disulfide + Water unknown Guanosine diphosphate + Thioredoxindetails
Gene Name:
NME2
Uniprot ID:
P22392
Reactions
Adenosine triphosphate + Guanosine diphosphate unknown ADP + Guanosine triphosphatedetails
Gene Name:
NME3
Uniprot ID:
Q13232
Reactions
Adenosine triphosphate + Guanosine diphosphate unknown ADP + Guanosine triphosphatedetails
Gene Name:
NME6
Uniprot ID:
O75414
Reactions
Adenosine triphosphate + Guanosine diphosphate unknown ADP + Guanosine triphosphatedetails
Gene Name:
ALG2
Uniprot ID:
Q9H553
Reactions
Guanosine diphosphate mannose + D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol unknown Guanosine diphosphate + D-Man-alpha-(1->3)-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-GlcNAc-diphosphodolicholdetails
Guanosine diphosphate mannose + D-Man-alpha-(1->3)-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolichol unknown Guanosine diphosphate + D-Man-alpha-(1->3)-(D-Man-alpha-(1->6))-D-Man-beta-(1->4)-D-GlcNAc-beta-(1->4)-D-GlcNAc-diphosphodolicholdetails
Gene Name:
DPM1
Uniprot ID:
O60762
Reactions
Guanosine diphosphate mannose + Dolichol-20 unknown Guanosine diphosphate + Dolichyl beta-D-mannosyl phosphatedetails
Guanosine diphosphate mannose + Dolichol-20 unknown Guanosine diphosphate + Dolichyl phosphate D-mannosedetails
Gene Name:
GMDS
Uniprot ID:
O60547
Gene Name:
FUT2
Uniprot ID:
Q10981
Reactions
GDP-L-fucose + beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide unknown Guanosine diphosphate + alpha-L-fucosyl-(1->2)-beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramidedetails
Gene Name:
FUT1
Uniprot ID:
P19526
Reactions
GDP-L-fucose + beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide unknown Guanosine diphosphate + alpha-L-fucosyl-(1->2)-beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramidedetails
Gene Name:
PFKP
Uniprot ID:
Q01813
Gene Name:
PFKL
Uniprot ID:
P17858
Gene Name:
PFKM
Uniprot ID:
P08237
Gene Name:
PKM
Uniprot ID:
P14618
Reactions
Guanosine triphosphate + Pyruvic acid unknown Guanosine diphosphate + Phosphoenolpyruvic aciddetails
Gene Name:
PKLR
Uniprot ID:
P30613
Reactions
Guanosine triphosphate + Pyruvic acid unknown Guanosine diphosphate + Phosphoenolpyruvic aciddetails
Gene Name:
ENTPD4
Uniprot ID:
Q9Y227
Reactions
Guanosine diphosphate + Water unknown Guanosine monophosphate + Phosphoric aciddetails
Gene Name:
ENTPD6
Uniprot ID:
O75354
Reactions
Guanosine diphosphate + Water unknown Guanosine monophosphate + Phosphoric aciddetails
Gene Name:
ENTPD5
Uniprot ID:
O75356
Reactions
Guanosine diphosphate + Water unknown Guanosine monophosphate + Phosphoric aciddetails
Gene Name:
ADSS
Uniprot ID:
P30520
Reactions
Guanosine triphosphate + Inosinic acid + L-Aspartic acid unknown Guanosine diphosphate + Phosphoric acid + Adenylsuccinic aciddetails
Guanosine triphosphate + Inosinic acid + L-Aspartic acid unknown Guanosine diphosphate + Phosphoric acid + N(6)-(1,2-dicarboxyethyl)AMPdetails
Gene Name:
ADSSL1
Uniprot ID:
Q8N142
Reactions
Guanosine triphosphate + Inosinic acid + L-Aspartic acid unknown Guanosine diphosphate + Phosphoric acid + Adenylsuccinic aciddetails
Guanosine triphosphate + Inosinic acid + L-Aspartic acid unknown Guanosine diphosphate + Phosphoric acid + N(6)-(1,2-dicarboxyethyl)AMPdetails
Gene Name:
SUCLG1
Uniprot ID:
P53597
Reactions
Guanosine triphosphate + Succinic acid + Coenzyme A unknown Guanosine diphosphate + Phosphoric acid + Succinyl-CoAdetails
Gene Name:
PCK2
Uniprot ID:
Q16822
Reactions
Guanosine triphosphate + Oxalacetic acid unknown Guanosine diphosphate + Phosphoenolpyruvic acid + CO(2)details
Guanosine triphosphate + Oxalacetic acid unknown Guanosine diphosphate + Phosphoenolpyruvic acid + Carbon dioxidedetails
Gene Name:
SUCLG2
Uniprot ID:
Q96I99
Reactions
Guanosine triphosphate + Succinic acid + Coenzyme A unknown Guanosine diphosphate + Phosphoric acid + Succinyl-CoAdetails
Gene Name:
PCK1
Uniprot ID:
P35558
Reactions
Guanosine triphosphate + Oxalacetic acid unknown Guanosine diphosphate + Phosphoenolpyruvic acid + CO(2)details
Guanosine triphosphate + Oxalacetic acid unknown Guanosine diphosphate + Phosphoenolpyruvic acid + Carbon dioxidedetails
Gene Name:
TSTA3
Uniprot ID:
Q13630
Gene Name:
GUK1
Uniprot ID:
Q16774
Reactions
Adenosine triphosphate + Guanosine monophosphate unknown ADP + Guanosine diphosphatedetails
Gene Name:
SUCLA2
Uniprot ID:
Q9P2R7
Reactions
Guanosine triphosphate + Succinic acid + Coenzyme A unknown Guanosine diphosphate + Phosphoric acid + Succinyl-CoAdetails
Gene Name:
FUT5
Uniprot ID:
Q11128
Reactions
GDP-L-fucose + beta-D-galactosyl-(1->3)-N-acetyl-D-glucosaminyl-R unknown Guanosine diphosphate + beta-D-galactosyl-(1->3)-(alpha-L-fucosyl-(1->4))-N-acetyl-beta-D-glucosaminyl-Rdetails
Gene Name:
RAPGEF2
Uniprot ID:
Q9Y4G8
Gene Name:
PNPT1
Uniprot ID:
Q8TCS8
Reactions
RNA + Phosphoric acid unknown RNA + Guanosine diphosphatedetails
Gene Name:
ARHGEF1
Uniprot ID:
Q92888
Gene Name:
ARHGDIG
Uniprot ID:
Q99819
Gene Name:
GDI1
Uniprot ID:
P31150
Gene Name:
MCF2
Uniprot ID:
P10911
Gene Name:
GDI2
Uniprot ID:
P50395
Gene Name:
ARHGDIA
Uniprot ID:
P52565
Gene Name:
ARHGDIB
Uniprot ID:
P52566

Only showing the first 50 proteins. There are 230 proteins in total.