| Record Information |
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:10:05 -0700 |
| HMDB ID |
HMDB01201 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
| Common Name |
Guanosine diphosphate |
| Description |
Guanosine 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 5'-GDP
- GDP
- Guanosine 5'-(trihydrogen pyrophosphate)
- Guanosine 5'-diphosphate
- Guanosine 5'-pyrophosphate
- Guanosine mono(trihydrogen diphosphate)
- Guanosine pyrophosphate
- Guanosine-5'-diphosphate
- Guanosine-diphosphate
- PpG
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| Chemical Formula |
C10H15N5O11P2 |
| Average Molecular Weight |
443.2005 |
| Monoisotopic Molecular Weight |
443.024329371 |
| 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 Number |
146-91-8 |
| 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 Key |
QGWNDRXFNXRZMB-UUOKFMHZSA-N |
| Chemical Taxonomy |
| Kingdom |
Organic Compounds |
| Super Class |
Nucleosides, Nucleotides, and Analogues |
| Class |
Purine Nucleotides |
| Sub Class |
Purine Ribonucleotides |
| Other Descriptors |
- Aromatic Heteropolycyclic Compounds
- Ribonucleotides(KEGG)
- guanosine 5'-phosphate(ChEBI)
- purine ribonucleoside 5'-diphosphate(ChEBI)
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| 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
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| Direct Parent |
Purine Ribonucleoside Diphosphates |
| Ontology |
| Status |
Detected and Quantified |
| Origin |
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| Biofunction |
- Component of Fructose and mannose metabolism
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| Application |
Not Available |
| Cellular locations |
- Cytoplasm
- Extracellular
- Mitochondria
- Nucleus
- Golgi apparatus
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| 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 |
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| Predicted Properties |
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| Spectra |
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| Biological Properties |
| Cellular Locations |
- Cytoplasm
- Extracellular
- Mitochondria
- Nucleus
- Golgi apparatus
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| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
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| Tissue Location |
Not Available
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| Pathways |
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| Normal Concentrations |
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| Blood |
Detected and Quantified |
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15.0 +/- 2.0 uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Blood |
Detected and Quantified |
|
18.0 +/- 8.0 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
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1.86 +/- 0.027 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
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| Abnormal Concentrations |
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| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
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2.11 +/- 1.93 uM |
Adult (>18 years old) |
Both |
Rachialgia |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
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4.05 +/- 0.03 uM |
Adult (>18 years old) |
Both |
Subarachnoid hemorrhage |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.99 +/- 1.32 uM |
Adult (>18 years old) |
Both |
Epilepsy |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
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2.55 +/- 1.62 uM |
Adult (>18 years old) |
Both |
Stroke |
Cerebral stroke
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| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
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2.59 +/- 1.77 uM |
Adult (>18 years old) |
Both |
Neuroinfection |
Not Available |
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| Associated Disorders and Diseases |
| Disease References |
| 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
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| 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
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| 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
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| 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
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| 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
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| Associated OMIM IDs |
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| External Links |
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB022487 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
8630  |
| KEGG Compound ID |
C00035  |
| BioCyc ID |
GDP-4-DEHYDRO-6-DEOXY-D-MANNOSE  |
| BiGG ID |
33599  |
| Wikipedia Link |
GDP  |
| NuGOwiki Link |
HMDB01201  |
| Metagene Link |
HMDB01201  |
| METLIN ID |
6077  |
| PubChem Compound |
8977  |
| PDB ID |
GDP  |
| ChEBI ID |
17552  |
| References |
| Synthesis Reference |
Edlin, 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 |
- 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
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| Enzymes |
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| Name: |
Galactoside 2-alpha-L-fucosyltransferase 2
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| Reactions: |
- GDP-beta-L-fucose + beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D- galactosyl-(1->4)-beta-D-glucosyl-(11)-ceramide = GDP + 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-(11)- ceramide [RN:R04081]
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| Gene Name: |
FUT2 |
| Uniprot ID: |
Q10981  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Galactoside 2-alpha-L-fucosyltransferase 1
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| Reactions: |
- GDP-beta-L-fucose + beta-D-galactosyl-(1->3)-N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D- galactosyl-(1->4)-beta-D-glucosyl-(11)-ceramide = GDP + 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-(11)- ceramide [RN:R04081]
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| Gene Name: |
FUT1 |
| Uniprot ID: |
P19526  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
GDP-L-fucose synthase
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| Reactions: |
- GDP-L-fucose + NADP+ = GDP-4-dehydro-6-deoxy-D-mannose + NADPH + H+ [RN:R05692]
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| Gene Name: |
TSTA3 |
| Uniprot ID: |
Q13630  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Alpha-(1,3)-fucosyltransferase
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| Reactions: |
- GDP-beta-L-fucose + beta-D-galactosyl-(1->3)-N-acetyl-D-glucosaminyl-R = GDP + beta-D-galactosyl-(1->3)-[alpha-L-fucosyl-(1->4)]-N-acetyl-beta-D- glucosaminyl-R [RN:R04553]
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| Gene Name: |
FUT5 |
| Uniprot ID: |
Q11128  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Alpha-(1,6)-fucosyltransferase
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| Reactions: |
- GDP-beta-L-fucose + N4-{N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl-(1->3)-[N- acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl-(1->6)]-beta-D- mannosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->4)-N-acetyl-beta-D- glucosaminyl}asparagine = GDP + N4-{N-acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl-(1->3)-[N- acetyl-beta-D-glucosaminyl-(1->2)-alpha-D-mannosyl-(1->6)]-beta-D- mannosyl-(1->4)-N-acetyl-beta-D-glucosaminyl-(1->4)-[alpha-L- fucosyl-(1->6)]-N-acetyl-beta-D-glucosaminyl}asparagine [RN:R05988]
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| Gene Name: |
FUT8 |
| Uniprot ID: |
Q9BYC5  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Dynamin-1
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| Reactions: |
- GTP + H2O = GDP + phosphate [RN:R00335]
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| Gene Name: |
DNM1 |
| Uniprot ID: |
Q05193  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Dynamin-2
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| Reactions: |
- GTP + H2O = GDP + phosphate [RN:R00335]
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| Gene Name: |
DNM2 |
| Uniprot ID: |
P50570  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Alpha-(1,3)-fucosyltransferase
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| Reactions: |
- GDP-beta-L-fucose + beta-D-galactosyl-(1->3)-N-acetyl-D-glucosaminyl-R = GDP + beta-D-galactosyl-(1->3)-[alpha-L-fucosyl-(1->4)]-N-acetyl-beta-D- glucosaminyl-R [RN:R04553]
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| Gene Name: |
FUT6 |
| Uniprot ID: |
P51993  |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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