Record Information
Version2.0
Creation Date2012-08-09 09:16:11 -0600
Update Date2015-09-13 12:56:16 -0600
Secondary Accession Numbers
  • ECMDB21421
Identification
Name:Ribitol
Description:Ribitol is a sugar alcohol with a 5-carbon chain that has a hydroxyl (OH group) attached to every carbon. Ribitol is found in the cell wall of Gram-positive bacteria, and forms part of the structure of riboflavin and flavin mononucleotide (FMN). (Wikipedia) In E. coli, ribitol (or more specifically D-ribitol) can act as an inhibitor of both L-arabinose isomerase and D-arabinose isomerase. (EcoCyc)
Structure
Thumb
Synonyms:
  • 1,2,3,4,5-pentanepentol
  • meso-ribitol
  • Adonit
  • Adonite
  • Adonitol
  • D-adonitol
  • D-Ribitol
  • Meso-ribitol
  • Pentitol
  • Ribitol
Chemical Formula:C5H12O5
Weight:Average: 152.1458
Monoisotopic: 152.068473494
InChI Key:HEBKCHPVOIAQTA-ZXFHETKHSA-N
InChI:InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5-
CAS number:488-81-3
IUPAC Name:(2R,3s,4S)-pentane-1,2,3,4,5-pentol
Traditional IUPAC Name:ribitol
SMILES:OC[C@H](O)[C@H](O)[C@H](O)CO
Chemical Taxonomy
Description belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:102-105 °C
Experimental Properties:
PropertyValueSource
Water Solubility:936 mg/mL [HMP experimental]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility664 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity32.44 m³·mol⁻¹ChemAxon
Polarizability14.38 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-0fr2-0930000000-5a1a8471040df361537cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0gba-0940000000-39c5ee90545f38856669View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-8941000000-a1eac40beaba679b545bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (5 TMS)splash10-00di-8930000000-85527d43cd5f10f959a8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0gb9-0962000000-9c177252fb79fd04ff8cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr2-0930000000-5a1a8471040df361537cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0gba-0940000000-39c5ee90545f38856669View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-8941000000-a1eac40beaba679b545bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-8930000000-85527d43cd5f10f959a8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gb9-0962000000-9c177252fb79fd04ff8cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dl-9100000000-738016d8bd07caed9cccView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-0a4i-6033900000-a5ac27dc62580d112ccdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00kb-9200000000-1c9444c33ee213e4aa4fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-05mo-9000000000-baf46067df2ebf3b854cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-3276d3005611fd3d415cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0901000000-7db5e452cb762f33fd3aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014j-8900000000-5ee7c2252ae88c5c0198View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-0900000000-47c7512c4671bb121a01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-001i-1900000000-b984613919de5add093cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0ufr-0901000000-616311fa40559ac618daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-014j-7900000000-c947bd6b615b2019d255View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-000i-0900000000-c7e6bce3675a8cd1566bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0a4i-0900000000-419f37e184ec82e4c123View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014j-8900000000-e69cc8758936cd2cbceaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-d6447ee4c80f85c44fefView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-1900000000-67203d89ca337c3cd9d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014j-7900000000-867bbfc363a4790dadc1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-c7e6bce3675a8cd1566bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0a4i-0900000000-419f37e184ec82e4c123View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-1900000000-fd63152f503ab1d4aa19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-d230735907e604c9d45aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-91a543c0d92a8d8d3c3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udu-9300000000-e06ed1bf8e262afac25aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btl-9100000000-b459e90a751cabc2a231View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-9000000000-4943c8a982ad5101e46fView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
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  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • Huck, J. H., Roos, B., Jakobs, C., van der Knaap, M. S., Verhoeven, N. M. (2004). "Evaluation of pentitol metabolism in mammalian tissues provides new insight into disorders of human sugar metabolism." Mol Genet Metab 82:231-237. Pubmed: 15234337
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • 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
  • 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID15963
HMDB IDHMDB00508
Pubchem Compound ID827
Kegg IDC00474
ChemSpider ID10254628
WikipediaRibitol
BioCyc IDRIBITOL
EcoCyc IDRIBITOL
Ligand ExpoRB0

Enzymes

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
A beta-D-glucuronoside + H(2)O = D-glucuronate + an alcohol
Gene Name:
uidA
Uniprot ID:
P05804
Molecular weight:
68447
Reactions
A beta-D-glucuronoside + H(2)O = D-glucuronate + an alcohol.