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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:53 UTC
HMDB IDHMDB0000508
Secondary Accession Numbers
  • HMDB00508
Metabolite 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
Data?1676999693
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 Molecular Weight152.1458
Monoisotopic Molecular Weight152.068473494
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
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
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular 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-3.770 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Placenta
  • Prostate
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Alzheimer's 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 ]
Colorectal cancer
  1. Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]
  2. 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 ]
  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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022083
KNApSAcK IDC00001171
Chemspider ID10254628
KEGG Compound IDC00474
BioCyc IDRIBITOL
BiGG ID35086
Wikipedia LinkRibitol
METLIN ID316
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID15963
Food Biomarker OntologyNot Available
VMH IDRBT
MarkerDB IDMDB00000177
Good Scents IDrw1216341
References
Synthesis ReferenceYamazaki, 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