Common Name

Ribitol Description

Ribitol is a metabolic end product formed by the reduction of ribose in human fibroblasts and erythrocytes (pentitol, sugar alcohol, polyol). Export of ribitol across the cell membrane indicates that can be cleared from the body without metabolic conversion. (PMID 15234337 ). Several inborn errors of metabolism with abnormal polyol concentrations in body fluids are known to date. Most of these defects can be diagnosed by the assessment of urinary concentrations of polyols. (PMID 16435188 ). Ribitol is normally absent in Breast milk. (PMID 16456418 ). Structure

Synonyms

Value Source AdonitolChEBI D-AdonitolChEBI L-RibitolChEBI 1,2,3,4,5-PentanepentolHMDB AdonitHMDB AdoniteHMDB PentitolHMDB

Chemical Formlia

C5H12O5 Average Molecliar Weight

152.1458 Monoisotopic Molecliar Weight

152.068473494 IUPAC Name

(2R,3s,4S)-pentane-1,2,3,4,5-pentol Traditional Name

ribitol CAS Registry Number

488-81-3 SMILES

OC[C@H](O)[C@H](O)[C@H](O)CO

InChI Identifier

InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5-

InChI Key

HEBKCHPVOIAQTA-ZXFHETKHSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic oxygen compounds Sub Class

Organooxygen compounds Direct Parent

Sugar alcohols Alternative Parents

  • Monosaccharides
  • Secondary alcohols
  • Polyols
  • Primary alcohols
  • Hydrocarbon derivatives
  • Substituents

  • Sugar alcohol
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
  • Molecliar Framework

    Aliphatic acyclic compounds External Descriptors

  • ribitol (CHEBI:15963 )
  • Ontology Status

    Detected and Quantified Origin

  • Endogenous
  • Biofunction

    Not Available Application

    Not Available Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point102 – 105 °CNot Available Boiling PointNot AvailableNot Available Water Solubility936 mg/mLNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility664.0 mg/mLALOGPS logP-2.5ALOGPS logP-3.1ChemAxon logS0.64ALOGPS pKa (Strongest Acidic)12.76ChemAxon pKa (Strongest Basic)-3ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count5ChemAxon Polar Surface Area101.15 Å2ChemAxon Rotatable Bond Count4ChemAxon Refractivity32.44 m3·mol-1ChemAxon Polarizability14.38 Å3ChemAxon Number of Rings0ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key GC-MS

    GC-MS Spectrum – GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-0fr2-0930000000-5a1a8471040df361537cView in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0gba-0940000000-39c5ee90545f38856669View in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-8941000000-a1eac40beaba679b545bView in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-8930000000-85527d43cd5f10f959a8View in MoNA GC-MS

    GC-MS Spectrum – GC-MS (5 TMS)splash10-0gb9-0962000000-9c177252fb79fd04ff8cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-00kb-9200000000-1c9444c33ee213e4aa4fView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-05mo-9000000000-baf46067df2ebf3b854cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-3276d3005611fd3d415cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0901000000-7db5e452cb762f33fd3aView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014j-8900000000-5ee7c2252ae88c5c0198View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-47c7512c4671bb121a01View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-1900000000-b984613919de5add093cView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0ufr-0901000000-616311fa40559ac618daView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014j-7900000000-c947bd6b615b2019d255View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-c7e6bce3675a8cd1566bView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-419f37e184ec82e4c123View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-APPI-QQ , positivesplash10-014j-8900000000-e69cc8758936cd2cbceaView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-APPI-QQ , positivesplash10-001i-0900000000-d6447ee4c80f85c44fefView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-APPI-QQ , positivesplash10-001i-1900000000-67203d89ca337c3cd9d1View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-APPI-QQ , positivesplash10-014j-7900000000-867bbfc363a4790dadc1View in MoNA 1D NMR

    1H NMR SpectrumNot Available 2D NMR

    [1H,13C] 2D NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Extracellliar
  • Biofluid Locations

  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
  • Tissue Location

  • Prostate
  • Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified2.5 (0.0 – 5.0) uMChildren (1-13 years old)BothNormal

  • 14988808
  • details BloodDetected and Quantified0.54 +/- 0.078 uMElderly (>65 years old)BothNormal

  • 8595727
  • details BloodDetected and Quantified0.460 (0.375-0.546) uMAdlit (>18 years old)BothNormal

  • 7710082
  • details Cerebrospinal Fluid (CSF)Detected and Quantified3.73 (3.01-4.45) uMAdlit (>18 years old)BothNormal

  • 7710082
  • details Cerebrospinal Fluid (CSF)Detected and Quantified17.8 (0.0-35.6) uMAdlit (>18 years old)BothNormal

  • 18502700
  • details Cerebrospinal Fluid (CSF)Detected and Quantified5.0 (0.0-10.0) uMAdlit (>18 years old)Not SpecifiedNormal

  • 11357181
  • details Cerebrospinal Fluid (CSF)Detected and Quantified3.64 +/- 0.67 uMElderly (>65 years old)BothNormal

  • 8595727
  • details FecesDetected but not Quantified Infant (0-1 year old)Both

    Normal

  • 22411374
  • details FecesDetected but not Quantified Adlit (>18 years old)Both

    Normal

  • 24029555
  • details UrineDetected and Quantified8.0 (5.0 – 11.0) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal

  • 14988808
  • details UrineDetected and Quantified3.5 +/- 2.24 umol/mmol creatinineAdlit (>18 years old)BothNormal

  • Geigy Scientific …
  • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified0.55 +/- 0.08 uMElderly (>65 years old)BothAlzheimers disease

  • 8595727
  • details BloodDetected but not Quantified Adlit (>18 years old)BothColorectal cancer

  • 25105552
  • details BloodDetected and Quantified20.0 (6.0–35.0) uMAdlit (>18 years old)BothRibose-5-phosphate isomerase deficiency

  • 14988808
  • details Cerebrospinal Fluid (CSF)Detected and Quantified3.8 +/- 0.68 uMElderly (>65 years old)BothAlzheimers disease

  • 8595727
  • details UrineDetected and Quantified154.5 (123.0-186.0) umol/mmol creatinineNewborn (0-30 days old)Not SpecifiedRibose-5-phosphate isomerase deficiency

  • 14988808
  • details

    Associated Disorders and Diseases Disease References

    Alzheimers disease

    1. Shetty HU, Holloway HW, Schapiro MB: Cerebrospinal fluid and plasma distribution of myo-inositol and other polyols in Alzheimer disease. Clin Chem. 1996 Feb;42(2):298-302. [PubMed:8595727 ]

    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

  • 104300 (Alzheimer's disease)
  • 608611 (Ribose-5-phosphate isomerase deficiency)
  • External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB022083 KNApSAcK ID

    Not Available Chemspider ID

    10254628 KEGG Compound ID

    C00474 BioCyc ID

    RIBITOL BiGG ID

    35086 Wikipedia Link

    Ribitol NuGOwiki Link

    HMDB00508 Metagene Link

    HMDB00508 METLIN ID

    316 PubChem Compound

    Not Available PDB ID

    RB0 ChEBI ID

    15963

    Product: Phorbol 12-myristate 13-acetate

    References Synthesis Reference Yamazaki, Masayoshi; Yamazaki, Fumito; Muranaka, Chikako; Kozeki, Satomi; Tatsuno, Yoshiaki; Okamoto, Naoki. Manufacture of ribitol with Trichosporonoides. Jpn. Kokai Tokkyo Koho (1999), 6 pp. 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. Roboz J, Kappatos DC, Greaves J, Holland JF: Determination of polyols in serum by selected ion monitoring. Clin Chem. 1984 Oct;30(10):1611-5. [PubMed:6434200 ]
    3. Shetty HU, Holloway HW, Rapoport SI: Capillary gas chromatography combined with ion trap detection for quantitative profiling of polyols in cerebrospinal fluid and plasma. Anal Biochem. 1995 Jan 1;224(1):279-85. [PubMed:7710082 ]
    4. Cavalli C, Teng C, Battaglia FC, Bevilacqua G: Free sugar and sugar alcohol concentrations in human breast milk. J Pediatr Gastroenterol Nutr. 2006 Feb;42(2):215-21. [PubMed:16456418 ]
    5. Wamelink MM, Smith DE, Jakobs C, Verhoeven NM: Analysis of polyols in urine by liquid chromatography-tandem mass spectrometry: a useful tool for recognition of inborn errors affecting polyol metabolism. J Inherit Metab Dis. 2005;28(6):951-63. [PubMed:16435188 ]
    6. Huck JH, Roos B, Jakobs C, van der Knaap MS, Verhoeven NM: Evaluation of pentitol metabolism in mammalian tissues provides new insight into disorders of human sugar metabolism. Mol Genet Metab. 2004 Jul;82(3):231-7. [PubMed:15234337 ]
    7. Georgescu C, Boboc F, Dumitrescu MR, Potcoava R, Florescu PD, Racovita D: [Identification of some atypical (morpho-cultural and enzymatic) characteristics of E. coli strains isolated in different clinical and epidemiological conditions]. Rev Ig Bacteriol Virusol Parazitol Epidemiol Pneumoftiziol Bacteriol Virusol Parazitol Epidemiol. 1980 Jan-Mar;25(1):17-26. [PubMed:6990452 ]
    8. Malnick H: Anaerobiospirillum thomasii sp. nov., an anaerobic spiral bacterium isolated from the feces of cats and dogs and from diarrheal feces of humans, and emendation of the genus Anaerobiospirillum. Int J Syst Bacteriol. 1997 Apr;47(2):381-4. [PubMed:9103625 ]
    9. De Baere T, Wauters G, Kampfer P, Labit C, Claeys G, Verschraegen G, Vaneechoutte M: Isolation of Buttiauxella gaviniae from a spinal cord patient with urinary bladder pathology. J Clin Microbiol. 2002 Oct;40(10):3867-70. [PubMed:12354904 ]
    10. Brenner DJ, Davis BR, Steigerwalt AG, Riddle CF, McWhorter AC, Allen SD, Farmer JJ 3rd, Saitoh Y, Fanning GR: Atypical biogroups of Escherichia coli found in clinical specimens and description of Escherichia hermannii sp. nov. J Clin Microbiol. 1982 Apr;15(4):703-13. [PubMed:7040466 ]
    11. Herzog C, Wood HC, Noel I, Booth JC: Comparison of a new enzyme-linked immunosorbent assay method with counterimmunoelectrophoresis for detection of teichoic acid antibodies in sera from patients with Staphylococcus aureus infections. J Clin Microbiol. 1984 Apr;19(4):511-5. [PubMed:6715518 ]
    12. Hickman-Brenner FW, Vohra MP, Huntley-Carter GP, Fanning GR, Lowery VA 3rd, Brenner DJ, Farmer JJ 3rd: Leminorella, a new genus of Enterobacteriaceae: identification of Leminorella grimontii sp. nov. and Leminorella richardii sp. nov. found in clinical specimens. J Clin Microbiol. 1985 Feb;21(2):234-9. [PubMed:3972991 ]
    13. Hickman-Brenner FW, Fanning GR, Arduino MJ, Brenner DJ, Farmer JJ 3rd: Aeromonas schubertii, a new mannitol-negative species found in human clinical specimens. J Clin Microbiol. 1988 Aug;26(8):1561-4. [PubMed:3139706 ]
    14. Konishi K, Yamagishi T, Sakamoto K: A Halophilic vibrio isolated from a case of chronic cholecystitis. Microbiol Immunol. 1981;25(12):1221-8. [PubMed:7334940 ]
    15. Brenner DJ, McWhorter AC, Kai A, Steigerwalt AG, Farmer JJ 3rd: Enterobacter asburiae sp. nov., a new species found in clinical specimens, and reassignment of Erwinia dissolvens and Erwinia nimipressuralis to the genus Enterobacter as Enterobacter dissolvens comb. nov. and Enterobacter nimipressuralis comb. nov. J Clin Microbiol. 1986 Jun;23(6):1114-20. [PubMed:3711302 ]
    16. Funke G, Lucchini GM, Pfyffer GE, Marchiani M, von Graevenitz A: Characteristics of CDC group 1 and group 1-like coryneform bacteria isolated from clinical specimens. J Clin Microbiol. 1993 Nov;31(11):2907-12. [PubMed:8263175 ]
    17. Aldova E, Hausner O, Kocmoud Z, Schindler J, Petras P: A new member of the family Enterobacteriaceae–Pragia fontium. J Hyg Epidemiol Microbiol Immunol. 1988;32(4):433-6. [PubMed:3221093 ]
    18. McWhorter AC, Haddock RL, Nocon FA, Steigerwalt AG, Brenner DJ, Aleksic S, Bockemuhl J, Farmer JJ 3rd: Trabulsiella guamensis, a new genus and species of the family Enterobacteriaceae that resembles Salmonella subgroups 4 and 5. J Clin Microbiol. 1991 Jul;29(7):1480-5. [PubMed:1885744 ]
    19. Podschun R: Phenotypic properties of Klebsiella pneumoniae and K. oxytoca isolated from different sources. Zentralbl Hyg Umweltmed. 1990 May;189(6):527-35. [PubMed:2200423 ]
    20. Yoshioka S, Kameyama K, Sanaka M, Sekine I, Kagimoto S, Fujitsuka S, Saitoh S: Effect of diabetes on the free polyol pattern in cataractous lenses. Clin Chem. 1991 May;37(5):686-9. [PubMed:2032321 ]
    21. Hudson MJ, Hollis DG, Weaver RE, Galvis CG: Relationship of CDC group EO-2 and psychrobacter immobilis. J Clin Microbiol. 1987 Oct;25(10):1907-10. [PubMed:3667912 ]
    22. Brisse S, van Himbergen T, Kusters K, Verhoef J: Development of a rapid identification method for Klebsiella pneumoniae phylogenetic groups and analysis of 420 clinical isolates. Clin Microbiol Infect. 2004 Oct;10(10):942-5. [PubMed:15373895 ]
    23. Roboz J, Kappatos DC, Holland JF: Role of individual serum pentitol concentrations in the diagnosis of disseminated visceral candidiasis. Eur J Clin Microbiol. 1987 Dec;6(6):708-14. [PubMed:3440465 ]
    24. Thaller MC, Berlutti F, Dainelli B, Pezzi R: New plate medium for screening and presumptive identification of gram-negative urinary tract pathogens. J Clin Microbiol. 1988 Apr;26(4):791-3. [PubMed:3366875 ]

    PMID: 19923353