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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:46:08 UTC
HMDB IDHMDB0000618
Secondary Accession Numbers
Metabolite Identification
Common NameD-Ribulose 5-phosphate
DescriptionD-Ribulose 5-phosphate belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. D-Ribulose 5-phosphate is a metabolite in the following pathways: pentose phosphate pathway, pentose and glucuronate interconversions, and riboflavin metabolism (KEGG). D-Ribulose 5-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Within humans, D-ribulose 5-phosphate participates in a number of enzymatic reactions. In particular, D-ribulose 5-phosphate can be converted into D-ribose 5-phosphate through its interaction with the enzyme ribose-5-phosphate isomerase. In addition, D-ribulose 5-phosphate can be converted into xylulose 5-phosphate; which is mediated by the enzyme ribulose-phosphate 3-epimerase. In humans, D-ribulose 5-phosphate is involved in pentose phosphate pathway. Outside of the human body, D-Ribulose 5-phosphate has been detected, but not quantified in, several different foods, such as winter squash, japanese chestnuts, barley, strawberries, and abiyuchs. This could make D-ribulose 5-phosphate a potential biomarker for the consumption of these foods. D-Ribulose 5-phosphate, with regard to humans, has been found to be associated with several diseases such as lewy body disease, frontotemporal dementia, and alzheimer's disease; D-ribulose 5-phosphate has also been linked to the inborn metabolic disorder transaldolase deficiency.
Structure
Thumb
Synonyms
ValueSource
D-Erythro-pent-2-ulose 5-(dihydrogen phosphate)ChEBI
D-Erythro-pent-2-ulose 5-(dihydrogen phosphoric acid)Generator
D-Ribulose 5-phosphoric acidGenerator
Ribulose 5-phosphateHMDB
Ribulose 5-phosphate, (D)-isomerHMDB
Ribulose 5-phosphate, (L)-isomerHMDB
Chemical FormulaC5H11O8P
Average Molecular Weight230.1098
Monoisotopic Molecular Weight230.01915384
IUPAC Name{[(2R,3R)-2,3,5-trihydroxy-4-oxopentyl]oxy}phosphonic acid
Traditional NameAra
CAS Registry Number4151-19-3
SMILES
OCC(=O)[C@H](O)[C@H](O)COP(O)(O)=O
InChI Identifier
InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h4-6,8-9H,1-2H2,(H2,10,11,12)/t4-,5+/m1/s1
InChI KeyFNZLKVNUWIIPSJ-UHNVWZDZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Acyloin
  • Beta-hydroxy ketone
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker140.85330932474
[M-H]-MetCCS_test_neg136.530932474
[M-H]-Not Available140.853http://allccs.zhulab.cn/database/detail?ID=AllCCS00001804
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
Biospecimen Locations
  • Blood
  • Cellular Cytoplasm
  • Saliva
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.82 +/- 0.22 uMAdult (>18 years old)BothTransaldolase deficiency details
SalivaDetected and Quantified3.41 +/- 1.80 uMAdult (>18 years old)MaleAlzheimer's disease details
SalivaDetected and Quantified3.16 +/- 1.86 uMAdult (>18 years old)MaleFrontotemporal lobe dementia details
SalivaDetected and Quantified4.74 +/- 4.64 uMAdult (>18 years old)BothLewy body disease details
Associated Disorders and Diseases
Disease References
Transaldolase deficiency
  1. Huck JH, Struys EA, Verhoeven NM, Jakobs C, van der Knaap MS: Profiling of pentose phosphate pathway intermediates in blood spots by tandem mass spectrometry: application to transaldolase deficiency. Clin Chem. 2003 Aug;49(8):1375-80. [PubMed:12881455 ]
Alzheimer's disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Frontotemporal dementia
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Lewy body disease
  1. Tsuruoka M, Hara J, Hirayama A, Sugimoto M, Soga T, Shankle WR, Tomita M: Capillary electrophoresis-mass spectrometry-based metabolome analysis of serum and saliva from neurodegenerative dementia patients. Electrophoresis. 2013 Oct;34(19):2865-72. doi: 10.1002/elps.201300019. Epub 2013 Sep 6. [PubMed:23857558 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022145
KNApSAcK IDNot Available
Chemspider ID388327
KEGG Compound IDC00199
BioCyc IDRIBULOSE-5P
BiGG IDNot Available
Wikipedia LinkRibulose_5-phosphate
METLIN IDNot Available
PubChem Compound439184
PDB IDNot Available
ChEBI ID17363
Food Biomarker OntologyNot Available
VMH IDRU5P_D
MarkerDB IDMDB00000201
Good Scents IDNot Available
References
Synthesis ReferenceWong, Chi-Huey; McCurry, Stephen D.; Whitesides, George M. Practical enzymic syntheses of ribulose 1,5 bisphosphate and ribose 5-phosphate. Journal of the American Chemical Society (1980), 102(27), 7938-9.
Material Safety Data Sheet (MSDS)Not Available
General References

Only showing the first 10 proteins. There are 15 proteins in total.

Enzymes

General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the synthesis of phosphoribosylpyrophosphate (PRPP) that is essential for nucleotide synthesis.
Gene Name:
PRPS1L1
Uniprot ID:
P21108
Molecular weight:
34838.915
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes with similar activities ADP-ribose ADP-mannose, ADP-glucose, 8-oxo-GDP and 8-oxo-dGDP. Can also hydrolyze other nucleotide sugars with low activity.
Gene Name:
NUDT5
Uniprot ID:
Q9UKK9
Molecular weight:
24327.41
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the synthesis of phosphoribosylpyrophosphate (PRPP) that is essential for nucleotide synthesis.
Gene Name:
PRPS1
Uniprot ID:
P60891
Molecular weight:
12324.195
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the synthesis of phosphoribosylpyrophosphate (PRPP) that is essential for nucleotide synthesis.
Gene Name:
PRPS2
Uniprot ID:
P11908
Molecular weight:
35054.06
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate (By similarity).
Gene Name:
TKTL1
Uniprot ID:
P51854
Molecular weight:
59302.195
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
Gene Name:
TKT
Uniprot ID:
P29401
Molecular weight:
67876.95
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative decarboxylation of 6-phosphogluconate to ribulose 5-phosphate and CO(2), with concomitant reduction of NADP to NADPH (By similarity).
Gene Name:
PGD
Uniprot ID:
P52209
Molecular weight:
53139.56
Reactions
6-Phosphogluconic acid + NADP → D-Ribulose 5-phosphate + CO(2) + NADPHdetails
6-Phosphogluconic acid + NADP → D-Ribulose 5-phosphate + Carbon dioxide + NADPH + Hydrogen Iondetails
General function:
Involved in ribokinase activity
Specific function:
Not Available
Gene Name:
RBKS
Uniprot ID:
Q9H477
Molecular weight:
34142.685
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
This enzyme participates in both the breakdown and synthesis of glucose.
Gene Name:
PGM1
Uniprot ID:
P36871
Molecular weight:
63789.985
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
Interconverts GlcNAc-6-P and GlcNAc-1-P.
Gene Name:
PGM3
Uniprot ID:
O95394
Molecular weight:
62940.905

Only showing the first 10 proteins. There are 15 proteins in total.