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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-05-29 19:25:21 UTC
HMDB IDHMDB00283
Secondary Accession NumbersNone
Metabolite Identification
Common NameD-Ribose
DescriptionD-ribose is commonly referred to simply as ribose, a five-carbon sugar found in all living cells. Ribose is not an essential nutrient because it can be synthesized by almost every tissue in the body from other substances, such as glucose. It is vital for life as a component of DNA, RNA, ATP, ADP, and AMP. In nature, small amounts of ribose can be found in ripe fruits and vegetables. Brewer's yeast, which has a high concentration of RNA, is another rich source of ribose. D-ribose is also a component of many so-called energy drinks and antiaging products available on the market today. Ribose is a structural component of ATP, which is the primary energy source for exercising muscle. The adenosine component is an adenine base attached to the five-carbon sugar ribose. ATP provides energy to working muscles by releasing a phosphate group, hence becoming ADP, which in turn may release a phosphate group, then becoming AMP. During intense muscular activity, the total amount of ATP available is quickly depleted. In an effort to correct this imbalance, AMP is broken down in the muscle and secreted from the cell. Once the breakdown products of AMP are released from the cell, the energy potential (TAN pool) of the muscle is reduced and ATP must then be reformed using ribose. Ribose helps restore the level of adenine nucleotides by bypassing the rate-limiting step in the de novo (oxidative pentose phosphate) pathway, which regenerates 5-phosphoribosyl-l-pyrophosphate (PRPP), the essential precursor for ATP. If ribose is not readily available to a cell, glucose may be converted to ribose. Ribose supplementation has been shown to increase the rate of ATP resynthesis following intense exercise. The use of ribose in men with severe coronary artery disease resulted in improved exercise tolerance. Hence, there is interest in the potential of ribose supplements to boost muscular performance in athletic activities. (PMID: 17618002 , Curr Sports Med Rep. 2007 Jul;6(4):254-7.).
Structure
Thumb
Synonyms
  1. alpha-D-Ribose
  2. alpha-D-Ribose-5
  3. alpha-delta-Ribose
  4. alpha-delta-Ribose-5
  5. D-(-)-Ribose
  6. D-Ribo-2,3,4,5-tetrahydroxyvaleraldehyde
  7. D-Ribose
  8. delta-(-)-Ribose
  9. delta-Ribo-2,3,4,5-tetrahydroxyvaleraldehyde
  10. delta-Ribose
  11. Ribose
Chemical FormulaC5H10O5
Average Molecular Weight150.1299
Monoisotopic Molecular Weight150.05282343
IUPAC Name(3R,4S,5R)-5-(hydroxymethyl)oxolane-2,3,4-triol
Traditional IUPAC NameD-ribofuranose
CAS Registry Number50-69-1
SMILES
OC[C@H]1OC(O)[C@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C5H10O5/c6-1-2-3(7)4(8)5(9)10-2/h2-9H,1H2/t2-,3-,4-,5?/m1/s1
InChI KeyHMFHBZSHGGEWLO-SOOFDHNKSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassPentoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • L-arabinose(ChEBI)
Substituents
  • 1,2 Diol
  • Hemiacetal
  • Oxolane
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentPentoses
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Second messenger
ApplicationNot Available
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point95 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.32HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility1070 g/LALOGPS
logP-2.6ALOGPS
logP-2.3ChemAxon
logS0.85ALOGPS
pKa (strongest acidic)11.31ChemAxon
pKa (strongest basic)-3ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count4ChemAxon
polar surface area90.15ChemAxon
rotatable bond count1ChemAxon
refractivity29.96ChemAxon
polarizability13.68ChemAxon
Spectra
SpectraGC-MSMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Adrenal Gland
  • Epidermis
  • Fibroblasts
  • Kidney
  • Lung
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Testes
Pathways
NameSMPDB LinkKEGG Link
Pentose Phosphate PathwaySMP00031map00030
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.3 (0.0-5.0) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.5 (0.0 - 5.0) uMAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified2.5 (0.0 - 5.0) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified3.0 (2.6-4.4) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified6.35 +/- 4.59 umol/mmol creatinineInfant (0-1 year old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.4 (0.0-5.0) uMAdult (>18 years old)BothRibose-5-phosphate isomerase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified90.0 (47.0 - 146.0) uMAdolescent (13-18 years old)BothRibose-5-phosphate isomerase deficiency details
UrineDetected and Quantified50.0 (5.0 - 102.0) umol/mmol creatinineAdolescent (13-18 years old)BothRibose-5-Phosphate Isomerase Deficiency details
Associated Disorders and Diseases
Disease References
Ribose-5-phosphate isomerase deficiency
  1. Huck JH, Verhoeven NM, Struys EA, Salomons GS, Jakobs C, van der Knaap MS: Ribose-5-phosphate isomerase deficiency: new inborn error in the pentose phosphate pathway associated with a slowly progressive leukoencephalopathy. Am J Hum Genet. 2004 Apr;74(4):745-51. Epub 2004 Feb 25. Pubmed: 14988808
Associated OMIM IDs
  • 608611 (Ribose-5-phosphate isomerase deficiency)
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB011145
KNApSAcK IDC00034198
Chemspider ID5575
KEGG Compound IDC00121
BioCyc IDCPD-560
BiGG ID33936
Wikipedia LinkRibose
NuGOwiki LinkHMDB00283
Metagene LinkHMDB00283
METLIN ID313
PubChem Compound5779
PDB ID1GQT
ChEBI ID16988
References
Synthesis ReferencePark, Yong-Cheol; Choi, Jin-Ho; Bennett, George N.; Seo, Jin-Ho. Characterization of D-ribose biosynthesis in Bacillus subtilis JY200 deficient in transketolase gene. Journal of Biotechnology (2006), 121(4), 508-516.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  2. Drel VR, Pacher P, Stevens MJ, Obrosova IG: Aldose reductase inhibition counteracts nitrosative stress and poly(ADP-ribose) polymerase activation in diabetic rat kidney and high-glucose-exposed human mesangial cells. Free Radic Biol Med. 2006 Apr 15;40(8):1454-65. Epub 2006 Jan 31. Pubmed: 16631535
  3. Dancis J, Lee J, Mendoza S, Liebes L: Nucleoside transport by perfused human placenta. Placenta. 1993 Sep-Oct;14(5):547-54. Pubmed: 8290494
  4. Quadrilatero J, Rush JW: Increased DNA fragmentation and altered apoptotic protein levels in skeletal muscle of spontaneously hypertensive rats. J Appl Physiol. 2006 Oct;101(4):1149-61. Epub 2006 Jun 15. Pubmed: 16778006
  5. Carloto A, Costas MJ, Cameselle JC, McLennan AG, Ribeiro JM: The specific, submicromolar-Km ADP-ribose pyrophosphatase purified from human placenta is enzymically indistinguishable from recombinant NUDT9 protein, including a selectivity for Mn2+ as activating cation and increase in Km for ADP-ribose, both elicited by H2O2. Biochim Biophys Acta. 2006 Oct;1760(10):1545-51. Epub 2006 Jun 9. Pubmed: 16860484
  6. Genovese T, Mazzon E, Di Paola R, Muia C, Crisafulli C, Caputi AP, Cuzzocrea S: ROLE OF ENDOGENOUS AND EXOGENOUS LIGANDS FOR THE PEROXISOME PROLIFERATOR-ACTIVATED RECEPTOR alpha IN THE DEVELOPMENT OF BLEOMYCIN-INDUCED LUNG INJURY. Shock. 2005 Dec;24(6):547-55. Pubmed: 16317386
  7. Abe H, Tanuma S: Properties of poly(ADP-ribose) glycohydrolase purified from pig testis nuclei. Arch Biochem Biophys. 1996 Dec 1;336(1):139-46. Pubmed: 8951044
  8. Augustin A, Muller-Steffner H, Schuber F: Molecular cloning and functional expression of bovine spleen ecto-NAD+ glycohydrolase: structural identity with human CD38. Biochem J. 2000 Jan 1;345 Pt 1:43-52. Pubmed: 10600637
  9. Dodd SL, Johnson CA, Fernholz K, St Cyr JA: The role of ribose in human skeletal muscle metabolism. Med Hypotheses. 2004;62(5):819-24. Pubmed: 15082114
  10. Cheng C, Zochodne DW: Sensory neurons with activated caspase-3 survive long-term experimental diabetes. Diabetes. 2003 Sep;52(9):2363-71. Pubmed: 12941777
  11. Szabo E, Virag L, Bakondi E, Gyure L, Hasko G, Bai P, Hunyadi J, Gergely P, Szabo C: Peroxynitrite production, DNA breakage, and poly(ADP-ribose) polymerase activation in a mouse model of oxazolone-induced contact hypersensitivity. J Invest Dermatol. 2001 Jul;117(1):74-80. Pubmed: 11442752
  12. Jacobson EL, Giacomoni PU, Roberts MJ, Wondrak GT, Jacobson MK: Optimizing the energy status of skin cells during solar radiation. J Photochem Photobiol B. 2001 Oct;63(1-3):141-7. Pubmed: 11684461
  13. Wurzer G, Herceg Z, Wesierska-Gadek J: Increased resistance to anticancer therapy of mouse cells lacking the poly(ADP-ribose) polymerase attributable to up-regulation of the multidrug resistance gene product P-glycoprotein. Cancer Res. 2000 Aug 1;60(15):4238-44. Pubmed: 10945636
  14. Okamoto H: The Reg gene family and Reg proteins: with special attention to the regeneration of pancreatic beta-cells. J Hepatobiliary Pancreat Surg. 1999;6(3):254-62. Pubmed: 10526060
  15. McNealy T, Frey M, Trojan L, Knoll T, Alken P, Michel MS: Intrinsic presence of poly (ADP-ribose) is significantly increased in malignant prostate compared to benign prostate cell lines. Anticancer Res. 2003 Mar-Apr;23(2B):1473-8. Pubmed: 12820412
  16. Alexy T, Toth A, Marton Z, Horvath B, Koltai K, Feher G, Kesmarky G, Kalai T, Hideg K, Sumegi B, Toth K: Inhibition of ADP-evoked platelet aggregation by selected poly(ADP-ribose) polymerase inhibitors. J Cardiovasc Pharmacol. 2004 Mar;43(3):423-31. Pubmed: 15076227
  17. Jiang Q, Wong J, Fyrst H, Saba JD, Ames BN: gamma-Tocopherol or combinations of vitamin E forms induce cell death in human prostate cancer cells by interrupting sphingolipid synthesis. Proc Natl Acad Sci U S A. 2004 Dec 21;101(51):17825-30. Epub 2004 Dec 13. Pubmed: 15596715
  18. Toth O, Szabo C, Kecskes M, Poto L, Nagy A, Losonczy H: In vitro effect of the potent poly(ADP-ribose) polymerase (PARP) inhibitor INO-1001 alone and in combination with aspirin, eptifibatide, tirofiban, enoxaparin or alteplase on haemostatic parameters. Life Sci. 2006 Jun 20;79(4):317-23. Epub 2006 Feb 9. Pubmed: 16480745
  19. Wall KA, Klis M, Kornet J, Coyle D, Ame JC, Jacobson MK, Slama JT: Inhibition of the intrinsic NAD+ glycohydrolase activity of CD38 by carbocyclic NAD analogues. Biochem J. 1998 Nov 1;335 ( Pt 3):631-6. Pubmed: 9794804
  20. Tamagno E, Parola M, Bardini P, Piccini A, Borghi R, Guglielmotto M, Santoro G, Davit A, Danni O, Smith MA, Perry G, Tabaton M: Beta-site APP cleaving enzyme up-regulation induced by 4-hydroxynonenal is mediated by stress-activated protein kinases pathways. J Neurochem. 2005 Feb;92(3):628-36. Pubmed: 15659232
  21. Boros LG, Steinkamp MP, Fleming JC, Lee WN, Cascante M, Neufeld EJ: Defective RNA ribose synthesis in fibroblasts from patients with thiamine-responsive megaloblastic anemia (TRMA). Blood. 2003 Nov 15;102(10):3556-61. Epub 2003 Jul 31. Pubmed: 12893755
  22. Takeda Y, Usukura M, Yoneda T, Oda N, Ito Y, Mabuchi H: The expression of messenger RNA for ADP-ribosyl cyclase in aldosterone-producing adenomas. Clin Endocrinol (Oxf). 2005 Apr;62(4):504-8. Pubmed: 15807884
  23. Thomas D, Yang H, Boffa DJ, Ding R, Sharma VK, Lagman M, Li B, Hering B, Mohanakumar T, Lakey J, Kapur S, Hancock WW, Suthanthiran M: Proapoptotic Bax is hyperexpressed in isolated human islets compared with antiapoptotic Bcl-2. Transplantation. 2002 Dec 15;74(11):1489-96. Pubmed: 12490780
  24. Dhanoa TS, Housner JA: Ribose: more than a simple sugar? Curr Sports Med Rep. 2007 Jul;6(4):254-7. Pubmed: 17618002

Enzymes

General function:
Involved in ribokinase activity
Specific function:
Not Available
Gene Name:
RBKS
Uniprot ID:
Q9H477
Molecular weight:
34142.685
Reactions
Adenosine triphosphate + D-Ribose → ADP + D-Ribose 5-phosphatedetails