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Record Information
Version1.0
Creation Date2016-05-27 02:03:50 UTC
Update Date2016-11-09 01:22:41 UTC
Accession NumberCHEM042467
Identification
Common Nameβ-D-ribofuranose
ClassSmall Molecule
DescriptionA D-Ribose having D-configuration.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical 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 Mass150.130 g/mol
Monoisotopic Mass150.053 g/mol
CAS Registry NumberNot Available
IUPAC Name(3R,4S,5R)-5-(hydroxymethyl)oxolane-2,3,4-triol
Traditional NameD-ribofuranoside
SMILESOC[C@H]1OC(O)[C@H](O)[C@@H]1O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 Area90.15 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity29.96 m³·mol⁻¹ChemAxon
Polarizability13.68 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0udi-0920000000-c414574c94624914be8cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0fk9-9831000000-d0b33cef6c46219ea9a8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0udi-0920000000-e3647dbf79b8733c3bfdView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0udi-0921000000-e8a202c64cf867b21cefView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0udi-0920000000-272c588a02a550b79c74View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0ldi-0941000000-999cd264e51df6d784b4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS)splash10-0udi-0910000000-54f42f17ff952d787b86View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0uxr-0920000000-d29b5079ba0fde220b0dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (4 TMS; 1 MEOX)splash10-0fk9-8920000000-71080ebc024c820bf8fdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-05cu-9300000000-e24e80da64b2475ddfd8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-0920000000-c414574c94624914be8cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0fk9-9831000000-d0b33cef6c46219ea9a8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-0920000000-e3647dbf79b8733c3bfdView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-0921000000-e8a202c64cf867b21cefView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-0920000000-272c588a02a550b79c74View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0ldi-0941000000-999cd264e51df6d784b4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0udi-0910000000-54f42f17ff952d787b86View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0uxr-0920000000-d29b5079ba0fde220b0dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0fk9-8920000000-71080ebc024c820bf8fdView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS)splash10-00g0-7349300000-49b1e72358e4fd020b5dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014r-4900000000-76daa3235c9f82ef4f5aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9100000000-b44f013dcb4efe64039dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-2900000000-6c1199d377747f0e5b49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-2900000000-8a9f89ac0a25c323249eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052p-9100000000-eaebbbf2fa629ce04160View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-6c48df798a58fc7029d9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-2900000000-816419eb5dad5bd99819View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9200000000-91d11d896b253dfd9693View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=9506998
2. Park, 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.
3. Scano P, Murgia A, Pirisi FM, Caboni P: A gas chromatography-mass spectrometry-based metabolomic approach for the characterization of goat milk compared with cow milk. J Dairy Sci. 2014 Oct;97(10):6057-66. doi: 10.3168/jds.2014-8247. Epub 2014 Aug 6.
4. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8
5. Characterization of the biochemical variability of bovine milk using metabolomics
6. Park, 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.
7. 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.
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15. Cheng C, Zochodne DW: Sensory neurons with activated caspase-3 survive long-term experimental diabetes. Diabetes. 2003 Sep;52(9):2363-71.
16. 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.
17. 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.
18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. 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.
24. 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.
25. 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.
26. 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.
27. 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.
28. 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.
29. 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.
30. Dhanoa TS, Housner JA: Ribose: more than a simple sugar? Curr Sports Med Rep. 2007 Jul;6(4):254-7.