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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:44:40 UTC
HMDB IDHMDB0000283
Secondary Accession Numbers
  • HMDB0012194
  • HMDB00283
  • HMDB12194
Metabolite Identification
Common NameD-Ribose
DescriptionD-Ribose, commonly referred to as simply ribose, is 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 anti-ageing 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 phosphoribosyl 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
Data?1582752120
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 Number613-83-2
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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point95 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-2.32HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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 Area90.15 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.28731661259
DarkChem[M-H]-128.43831661259
AllCCS[M+H]+134.33332859911
AllCCS[M-H]-124.84532859911
DeepCCS[M+H]+132.71730932474
DeepCCS[M-H]-130.53630932474
DeepCCS[M-2H]-165.40130932474
DeepCCS[M+Na]+139.98230932474
AllCCS[M+H]+134.332859911
AllCCS[M+H-H2O]+130.032859911
AllCCS[M+NH4]+138.432859911
AllCCS[M+Na]+139.532859911
AllCCS[M-H]-124.832859911
AllCCS[M+Na-2H]-126.532859911
AllCCS[M+HCOO]-128.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
D-RiboseOC[C@H]1OC(O)[C@H](O)[C@@H]1O3078.5Standard polar33892256
D-RiboseOC[C@H]1OC(O)[C@H](O)[C@@H]1O1491.1Standard non polar33892256
D-RiboseOC[C@H]1OC(O)[C@H](O)[C@@H]1O1406.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-Ribose,1TMS,isomer #1C[Si](C)(C)OC[C@H]1OC(O)[C@H](O)[C@@H]1O1505.7Semi standard non polar33892256
D-Ribose,1TMS,isomer #2C[Si](C)(C)OC1O[C@H](CO)[C@@H](O)[C@H]1O1544.9Semi standard non polar33892256
D-Ribose,1TMS,isomer #3C[Si](C)(C)O[C@H]1C(O)O[C@H](CO)[C@H]1O1526.5Semi standard non polar33892256
D-Ribose,1TMS,isomer #4C[Si](C)(C)O[C@@H]1[C@@H](CO)OC(O)[C@@H]1O1518.1Semi standard non polar33892256
D-Ribose,2TMS,isomer #1C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](O)[C@@H]1O1596.6Semi standard non polar33892256
D-Ribose,2TMS,isomer #2C[Si](C)(C)OC[C@H]1OC(O)[C@H](O[Si](C)(C)C)[C@@H]1O1575.7Semi standard non polar33892256
D-Ribose,2TMS,isomer #3C[Si](C)(C)OC[C@H]1OC(O)[C@H](O)[C@@H]1O[Si](C)(C)C1564.9Semi standard non polar33892256
D-Ribose,2TMS,isomer #4C[Si](C)(C)OC1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O1574.0Semi standard non polar33892256
D-Ribose,2TMS,isomer #5C[Si](C)(C)OC1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C1572.6Semi standard non polar33892256
D-Ribose,2TMS,isomer #6C[Si](C)(C)O[C@H]1C(O)O[C@H](CO)[C@H]1O[Si](C)(C)C1563.3Semi standard non polar33892256
D-Ribose,3TMS,isomer #1C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O1646.3Semi standard non polar33892256
D-Ribose,3TMS,isomer #2C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](O)[C@@H]1O[Si](C)(C)C1623.2Semi standard non polar33892256
D-Ribose,3TMS,isomer #3C[Si](C)(C)OC[C@H]1OC(O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C1633.0Semi standard non polar33892256
D-Ribose,3TMS,isomer #4C[Si](C)(C)OC1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C1606.1Semi standard non polar33892256
D-Ribose,4TMS,isomer #1C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C1603.5Semi standard non polar33892256
D-Ribose,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1OC(O)[C@H](O)[C@@H]1O1731.7Semi standard non polar33892256
D-Ribose,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1O[C@H](CO)[C@@H](O)[C@H]1O1753.8Semi standard non polar33892256
D-Ribose,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]1C(O)O[C@H](CO)[C@H]1O1746.3Semi standard non polar33892256
D-Ribose,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)OC(O)[C@@H]1O1746.3Semi standard non polar33892256
D-Ribose,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O2028.4Semi standard non polar33892256
D-Ribose,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1OC(O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2021.9Semi standard non polar33892256
D-Ribose,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1OC(O)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2013.5Semi standard non polar33892256
D-Ribose,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O2022.7Semi standard non polar33892256
D-Ribose,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1O[C@H](CO)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C2015.4Semi standard non polar33892256
D-Ribose,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)O[C@H]1C(O)O[C@H](CO)[C@H]1O[Si](C)(C)C(C)(C)C2028.0Semi standard non polar33892256
D-Ribose,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O2304.0Semi standard non polar33892256
D-Ribose,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C2306.4Semi standard non polar33892256
D-Ribose,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC[C@H]1OC(O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2310.8Semi standard non polar33892256
D-Ribose,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C2290.3Semi standard non polar33892256
D-Ribose,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C2543.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0udi-0920000000-c414574c94624914be8c2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0fk9-9831000000-d0b33cef6c46219ea9a82014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0udi-0920000000-e3647dbf79b8733c3bfd2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0udi-0921000000-e8a202c64cf867b21cef2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0udi-0920000000-272c588a02a550b79c742014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0ldi-0941000000-999cd264e51df6d784b42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0udi-0910000000-54f42f17ff952d787b862014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0uxr-0920000000-d29b5079ba0fde220b0d2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS; 1 MEOX)splash10-0fk9-8920000000-71080ebc024c820bf8fd2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-c414574c94624914be8c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized)splash10-0fk9-9831000000-d0b33cef6c46219ea9a82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-e3647dbf79b8733c3bfd2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized)splash10-0udi-0921000000-e8a202c64cf867b21cef2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized)splash10-0udi-0920000000-272c588a02a550b79c742017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized)splash10-0ldi-0941000000-999cd264e51df6d784b42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized)splash10-0udi-0910000000-54f42f17ff952d787b862017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized)splash10-0uxr-0920000000-d29b5079ba0fde220b0d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - D-Ribose GC-EI-TOF (Non-derivatized)splash10-0fk9-8920000000-71080ebc024c820bf8fd2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Ribose GC-MS (Non-derivatized) - 70eV, Positivesplash10-05cu-9300000000-e24e80da64b2475ddfd82016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Ribose GC-MS (4 TMS) - 70eV, Positivesplash10-00g0-7349300000-49b1e72358e4fd020b5d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Ribose GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Ribose GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Ribose GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Ribose GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - D-Ribose GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Ribose Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-014r-4900000000-76daa3235c9f82ef4f5a2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Ribose Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-000i-9100000000-b44f013dcb4efe64039d2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Ribose 35V, Negative-QTOFsplash10-0a4i-9000000000-64a1b88f0cb22f5b729a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Ribose 35V, Negative-QTOFsplash10-0a4i-9000000000-a05552744534bc6dc8c52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Ribose 20V, Negative-QTOFsplash10-0a4i-9000000000-23b475cbcd2c9fafde182021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Ribose 10V, Negative-QTOFsplash10-0a4i-9000000000-88ff2c607ed1b08ed6b92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Ribose 35V, Negative-QTOFsplash10-0a4i-9000000000-7c7662a3e6e7923d84cb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Ribose 35V, Negative-QTOFsplash10-0a4i-9000000000-ce0d2af497d6da39f1f12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Ribose 35V, Negative-QTOFsplash10-0a4i-9000000000-f0409fb19110a197badc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Ribose 35V, Negative-QTOFsplash10-0udi-8900000000-41d386e0f57f435290c82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - D-Ribose 40V, Negative-QTOFsplash10-0a4i-9300000000-2ea2e21fb5412f962d7f2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Ribose 10V, Positive-QTOFsplash10-0ue9-2900000000-6c1199d377747f0e5b492016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Ribose 20V, Positive-QTOFsplash10-0f89-2900000000-8a9f89ac0a25c323249e2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Ribose 40V, Positive-QTOFsplash10-052p-9100000000-eaebbbf2fa629ce041602016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Ribose 10V, Negative-QTOFsplash10-0002-1900000000-6c48df798a58fc7029d92016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Ribose 20V, Negative-QTOFsplash10-001j-2900000000-816419eb5dad5bd998192016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Ribose 40V, Negative-QTOFsplash10-0006-9200000000-91d11d896b253dfd96932016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Ribose 10V, Positive-QTOFsplash10-0gc0-1900000000-346af5e1437ac746833b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Ribose 20V, Positive-QTOFsplash10-0nc4-9400000000-74fd6af917cb088bef2b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Ribose 40V, Positive-QTOFsplash10-0a4i-9000000000-55c82f4fa793a5fd288b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Ribose 10V, Negative-QTOFsplash10-0pc1-5900000000-6953077be254812d8b252021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Ribose 20V, Negative-QTOFsplash10-0a4i-9100000000-fcc3022a655e16f83b2c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - D-Ribose 40V, Negative-QTOFsplash10-0006-9000000000-750ecddfae4eefc719962021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Adrenal Gland
  • Epidermis
  • Fibroblasts
  • Kidney
  • Lung
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified1131.0205 +/- 706.721 nmol/g wet fecesNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
FecesDetected and Quantified1494 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified2199 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
FecesDetected and Quantified1184 nmol/g wet fecesAdult (>18 years old)Not Specified
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified2.5 (0.0 - 5.0) umol/mmol creatinineAdolescent (13-18 years old)BothNormal details
UrineDetected and Quantified39.757 +/- 18.872 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>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
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified50.0 (5.0 - 102.0) umol/mmol creatinineAdolescent (13-18 years old)BothRibose-5-Phosphate Isomerase Deficiency details
UrineDetected and Quantified26.892 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Bladder cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
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 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
  • 114500 (Colorectal cancer)
  • 608611 (Ribose-5-phosphate isomerase deficiency)
  • 610247 (Eosinophilic esophagitis)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB031292
KNApSAcK IDC00034198
Chemspider ID5575
KEGG Compound IDC00121
BioCyc IDNot Available
BiGG ID33936
Wikipedia LinkRibose
METLIN ID313
PubChem Compound5779
PDB IDNot Available
ChEBI ID47013
Food Biomarker OntologyNot Available
VMH IDRIB_D
MarkerDB IDMDB00000133
Good Scents IDNot Available
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. doi: 10.1038/nature07762. [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 (1985). 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 ]
  25. Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]
  26. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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