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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 20:22:32 UTC
NP-MRD IDNP0000075
Secondary Accession NumbersNone
Natural Product Identification
Common NameRibitol
DescriptionRibitol is a pentose alcohol formed by the reduction of ribose. It occurs naturally in plants as well as in the cell walls of some Gram-positive bacteria. Ribitol forms part of the chemical structure of riboflavin and flavin mononucleotide (FMN). It is also a metabolic end product formed by the reduction of ribose in human fibroblasts and erythrocytes. In this regard ribitol is found in all organisms from bacteria to plants to humans. Ribitol is a normal constituent of human urine (PMID: 2736321 ). Elevated levels of ribitol in the serum or urine can be found in patients with transaldolase deficiency (PMID: 11283793 ). Transaldolase is an important enzyme in the pentose phosphate pathway (PPP). Elevated levels of ribitol in the serum or urine can be found in patients with Ribose-5-phosphate isomerase deficiency (PMID: 14988808 ). Ribose-5-phosphate isomerase is an important enzyme in the pentose phosphate pathway (PPP). Export of ribitol across the cell membrane indicates that can be cleared from the body without metabolic conversion (PMID 15234337 ). Ribitol is normally absent in Breast milk (PMID 16456418 ).
Structure
Thumb
Synonyms
ValueSource
(2R,3S,4S)-Pentane-1,2,3,4,5-pentolChEBI
AdonitolChEBI
D-AdonitolChEBI
D-RibitolChEBI
L-RibitolChEBI
1,2,3,4,5-PentanepentolHMDB
AdonitHMDB
AdoniteHMDB
PentitolHMDB
Chemical FormulaC5H12O5
Average Mass152.1458 Da
Monoisotopic Mass152.06847 Da
IUPAC Name(2R,3s,4S)-pentane-1,2,3,4,5-pentol
Traditional Nameribitol
CAS Registry Number488-81-3
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 KeyHEBKCHPVOIAQTA-ZXFHETKHSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-08-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, simulated)Varshavi.d262021-08-16View Spectrum
Species
Species of Origin
Species NameSourceReference
Adonis vernalisKNApSAcK Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Anthriscus sylvestrisKNApSAcK Database
Arabidopsis thalianaLOTUS Database
Bergera koenegii-
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Brassica oleracea L. ssp. BotrytisKNApSAcK Database
Bubalus bubalisFooDB
Bupleurum aureumLOTUS Database
Bupleurum falcatumKNApSAcK Database
Bupleurum fruticescensLOTUS Database
Bupleurum gibraltaricumLOTUS Database
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
Citrus X sinensis (L.) Osbeck (pro. sp.)Plant
ColumbaFooDB
ColumbidaeFooDB
Curcuma domesticaKNApSAcK Database
Curcuma longaPlant
Daphnia magnaLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Eugenia lehmanniiKNApSAcK Database
Evernia prunastriLOTUS Database
Gallus gallusFooDB
Homo sapiensLOTUS Database
Homo sapiens (Urine)Animalia
Laetiporus sulphureusLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Lotus burttiiLOTUS Database
Lotus corniculatusLOTUS Database
Medicago sativaLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Murraya paniculataPlant
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Phoma medicaginisFungi
Prunus aviumPlant
Solanum tuberosumKNApSAcK Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Serum)KNApSAcK Database
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
StateSolid
Experimental Properties
PropertyValueReference
Melting Point102 - 105 °CNot Available
Boiling Point494.50 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility936 mg/mLNot Available
LogP-3.224https://www.chemspider.com/Chemical-Structure.10254628.html
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000508
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022083
KNApSAcK IDC00001171
Chemspider ID10254628
KEGG Compound IDC00474
BioCyc IDRIBITOL
BiGG ID35086
Wikipedia LinkRibitol
METLIN ID316
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID15963
Good Scents IDrw1216341
References
General References
  1. Verhoeven NM, Huck JH, Roos B, Struys EA, Salomons GS, Douwes AC, van der Knaap MS, Jakobs C: Transaldolase deficiency: liver cirrhosis associated with a new inborn error in the pentose phosphate pathway. Am J Hum Genet. 2001 May;68(5):1086-92. Epub 2001 Mar 27. [PubMed:11283793 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. 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 ]
  19. 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 ]
  20. 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 ]
  21. 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 ]
  22. 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 ]
  23. 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 ]
  24. 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 ]
  25. 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 ]
  26. 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 ]
  27. Haga H, Nakajima T: Determination of polyol profiles in human urine by capillary gas chromatography. Biomed Chromatogr. 1989 Mar;3(2):68-71. doi: 10.1002/bmc.1130030206. [PubMed:2736321 ]