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Record Information
Version1.0
Creation Date2016-07-13 19:42:56 UTC
Update Date2016-07-20 20:50:56 UTC
LmdbLMDB00126
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
ValueSource
(3R,4S,5R)-5-(Hydroxymethyl)tetrahydrofuran-2,3,4-triolChEBI
RiboseChEBI
D-RibofuranosideHMDB
D-​RibofuranoseHMDB
RibofuranosideHMDB
RibofuranoseHMDB
Chemical FormulaC5H10O5
Average Molecular Weight150.1299
Monoisotopic Molecular Weight150.05282343
IUPAC Name(3R,4S,5R)-5-(hydroxymethyl)oxolane-2,3,4-triol
Traditional NameD-ribofuranoside
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
Description belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentoses
Alternative Parents
Substituents
  • Pentose monosaccharide
  • Tetrahydrofuran
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 Area90.15 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity29.96 m³·mol⁻¹ChemAxon
Polarizability13.68 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0udi-0920000000-c414574c94624914be8cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0fk9-9831000000-d0b33cef6c46219ea9a8Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0udi-0920000000-e3647dbf79b8733c3bfdSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0udi-0921000000-e8a202c64cf867b21cefSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0udi-0920000000-272c588a02a550b79c74Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0ldi-0941000000-999cd264e51df6d784b4Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0udi-0910000000-54f42f17ff952d787b86Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0uxr-0920000000-d29b5079ba0fde220b0dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS; 1 MEOX)splash10-0fk9-8920000000-71080ebc024c820bf8fdSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-c414574c94624914be8cSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fk9-9831000000-d0b33cef6c46219ea9a8Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-e3647dbf79b8733c3bfdSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0921000000-e8a202c64cf867b21cefSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-272c588a02a550b79c74Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ldi-0941000000-999cd264e51df6d784b4Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0910000000-54f42f17ff952d787b86Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-0920000000-d29b5079ba0fde220b0dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fk9-8920000000-71080ebc024c820bf8fdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05cu-9300000000-e24e80da64b2475ddfd8Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00g0-7349300000-49b1e72358e4fd020b5dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014r-4900000000-76daa3235c9f82ef4f5aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9100000000-b44f013dcb4efe64039dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-9000000000-64a1b88f0cb22f5b729aSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-9000000000-a05552744534bc6dc8c5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-23b475cbcd2c9fafde18Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9000000000-88ff2c607ed1b08ed6b9Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-9000000000-7c7662a3e6e7923d84cbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-9000000000-ce0d2af497d6da39f1f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-9000000000-f0409fb19110a197badcSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0udi-8900000000-41d386e0f57f435290c8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9300000000-2ea2e21fb5412f962d7fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-2900000000-6c1199d377747f0e5b49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-2900000000-8a9f89ac0a25c323249eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052p-9100000000-eaebbbf2fa629ce04160Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-6c48df798a58fc7029d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-2900000000-816419eb5dad5bd99819Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-91d11d896b253dfd9693Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gc0-1900000000-346af5e1437ac746833bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0nc4-9400000000-74fd6af917cb088bef2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-55c82f4fa793a5fd288bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pc1-5900000000-6953077be254812d8b25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9100000000-fcc3022a655e16f83b2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-750ecddfae4eefc71996Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Feces
  • Kidney perfusate
  • Milk
  • Plasma
  • Ruminal Fluid
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Kidney perfusateDetected but not QuantifiedNot ApplicableNot AvailablePorcine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Ruminal FluidDetected and Quantified255 +/- 78 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified258 +/- 38 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified312 +/- 40 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified312 +/- 40 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified323 +/- 70 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified406 +/- 95 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified219 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified237 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified238 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified298 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified254.5 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified311.4 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified322.9 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified406.5 uMNot AvailableBovine details
DrugBank IDNot Available
HMDB IDHMDB0000283
FooDB IDFDB031292
Phenol Explorer IDNot Available
KNApSAcK IDC00034198
BiGG ID33936
BioCyc IDNot Available
METLIN ID313
PDB IDNot Available
Wikipedia LinkRibose
Chemspider ID5575
ChEBI ID47013
PubChem Compound ID5779
Kegg Compound IDC00121
YMDB IDYMDB00253
ECMDB IDECMDB00283
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Dhanoa TS, Housner JA: Ribose: more than a simple sugar? Curr Sports Med Rep. 2007 Jul;6(4):254-7. [17618002 ]