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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-06-15 17:04:52 UTC
HMDB IDHMDB0001266
Secondary Accession Numbers
  • HMDB01266
Metabolite Identification
Common NameL-Sorbose
DescriptionL-Sorbose, also known as L-sorbinose or L-xylo-hexulose, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. L-Sorbose is an extremely weak basic (essentially neutral) compound (based on its pKa). L-Sorbose exists in all living species, ranging from bacteria to humans. The commercial production of vitamin C (ascorbic acid) often begins with sorbose. L-Sorbose (CAS: 87-79-6) is a ketose belonging to the group of sugars known as monosaccharides. Sorbose has been found to be a metabolites of Ketogulonicigenium (PMID: 15785002 ).
Structure
Data?1582752188
Synonyms
ValueSource
alpha-L-SorbopyranoseHMDB
Hex-2-uloseHMDB
L(-) Sorbose for biochemistryHMDB
L(-)-SorboseHMDB
L-(-)-SorboseHMDB
L-(-)-Sorbose 99%HMDB
L-1,3,4,5,6-Pentahydroxyhexan-2-oneHMDB
L-SorbinoseHMDB
L-Xylo-2-hexuloseHMDB
L-Xylo-hexuloseHMDB
SorbinHMDB
SorbinoseHMDB
SorboseHMDB
Xylo-hexuloseHMDB
alpha-L-Xylo-hexopyranos-2-uloseHMDB
Α-L-xylo-hexopyranos-2-uloseHMDB
Α-L-sorbopyranoseHMDB
a-L-SorbopyranoseGenerator
Chemical FormulaC6H12O6
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
IUPAC Name(2R,3S,4R,5S)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional Nameα-L-sorbopyranose
CAS Registry Number470-15-5
SMILES
OC[C@@]1(O)OC[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C6H12O6/c7-2-6(11)5(10)4(9)3(8)1-12-6/h3-5,7-11H,1-2H2/t3-,4+,5-,6+/m0/s1
InChI KeyLKDRXBCSQODPBY-BGPJRJDNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point165 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility360 mg/mL at 17 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1190 g/LALOGPS
logP-2.5ALOGPS
logP-2.8ChemAxon
logS0.82ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity36.36 m³·mol⁻¹ChemAxon
Polarizability16.05 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08fr-9700000000-3e5e0a3aa6c676c97701Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-004i-8422790000-fda815da7846441c6ea7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0900000000-ad56c2283c4948268668Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00ri-9600000000-f53f9ae5db12b8c07611Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0079-9200000000-c3dabd4edd0fd062cfd4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-014681a0ceccca243630Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-2900000000-fdd4f1c2b01b7cd4a621Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c30-9200000000-a3afc1e71049f23145b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fu-9700000000-86b1b9f75df959e2158fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-024i-9800000000-1acd95dd1e6f8744308fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-545f59c3707e4298b57cSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
  • Sweat
  • Urine
Tissue Locations
  • Adipose Tissue
  • Fibroblasts
  • Intestine
  • Kidney
  • Neuron
  • Pancreas
  • Placenta
  • Platelet
  • Prostate
  • Skeletal Muscle
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SweatDetected but not Quantified Adult BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified0.5 (0.0-1.0) umol/mmol creatinineAdult (>18 years old)Both
Prostate Cancer
details
UrineDetected but not Quantified Adult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
Prostate cancer
  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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001126
KNApSAcK IDNot Available
Chemspider ID390208
KEGG Compound IDC08356
BioCyc IDSORBOSE
BiGG IDNot Available
Wikipedia LinkSorbose
METLIN ID6121
PubChem Compound441484
PDB IDSOE
ChEBI ID10295
Food Biomarker OntologyNot Available
VMH IDSRB_L
References
Synthesis ReferenceBanjopnoppakun, Tanaphat; Moonmangmee, Somporn; Moonmangmee, Duangtip. Production of L-sorbose by thermotolerant acetic acid bacteria. Proceeding of the Kasetsart University Annual Conference, 44th, Bangkok, Thailand, Jan. 30-Feb. 2, 2006 (2006), 117-123.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Wang C, So SY, Wong KK, So WW, Chan SY: Chronic sinopulmonary disease in Chinese patients with obstructive azoospermia. J Androl. 1987 Jul-Aug;8(4):225-9. [PubMed:3624059 ]
  2. Gryz EA, Galicka-Latala D, Szczudlik A, Sieradzki J: [Etiopathogenesis of diabetic neuropathy]. Przegl Lek. 2000;57(12):727-31. [PubMed:11398597 ]
  3. Kossi J, Peltonen J, Uotila P, Laato M: Differential effects of hexoses and sucrose, and platelet-derived growth factor isoforms on cyclooxygenase-1 and -2 mRNA expression in keloid, hypertrophic scar and granulation tissue fibroblasts. Arch Dermatol Res. 2001 Mar;293(3):126-32. [PubMed:11357226 ]
  4. Gross KC, Houghton MP, Senterfit LB: Presumptive speciation of Streptococcus bovis and other group D streptococci from human sources by using arginine and pyruvate tests. J Clin Microbiol. 1975 Jan;1(1):54-60. [PubMed:1176592 ]
  5. Fukasawa M, Takayama E, Shinomiya N, Okumura A, Rokutanda M, Yamamoto N, Sakakibara R: Identification of the promoter region of human placental 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase gene. Biochem Biophys Res Commun. 2000 Jan 27;267(3):703-8. [PubMed:10673355 ]
  6. Le KA, Tappy L: Metabolic effects of fructose. Curr Opin Clin Nutr Metab Care. 2006 Jul;9(4):469-75. [PubMed:16778579 ]
  7. Fukasawa M, Tsuchiya T, Takayama E, Shinomiya N, Uyeda K, Sakakibara R, Seki S: Identification and characterization of the hypoxia-responsive element of the human placental 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase gene. J Biochem. 2004 Sep;136(3):273-7. [PubMed:15598882 ]
  8. Yanez AJ, Bertinat R, Spichiger C, Carcamo JG, de Los Angeles Garcia M, Concha II, Nualart F, Slebe JC: Novel expression of liver FBPase in Langerhans islets of human and rat pancreas. J Cell Physiol. 2005 Oct;205(1):19-24. [PubMed:15965961 ]
  9. Lee YH, Li Y, Uyeda K, Hasemann CA: Tissue-specific structure/function differentiation of the liver isoform of 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase. J Biol Chem. 2003 Jan 3;278(1):523-30. Epub 2002 Oct 11. [PubMed:12379646 ]
  10. Minchenko O, Opentanova I, Minchenko D, Ogura T, Esumi H: Hypoxia induces transcription of 6-phosphofructo-2-kinase/fructose-2,6-biphosphatase-4 gene via hypoxia-inducible factor-1alpha activation. FEBS Lett. 2004 Oct 8;576(1-2):14-20. [PubMed:15474002 ]
  11. Andrade-Rocha FT: Physical analysis of ejaculate to evaluate the secretory activity of the seminal vesicles and prostate. Clin Chem Lab Med. 2005;43(11):1203-10. [PubMed:16232086 ]
  12. Roy S, Banerjee A, Pandey HC, Singh G, Kumari GL: Application of seminal germ cell morphology and semen biochemistry in the diagnosis and management of azoospermic subjects. Asian J Androl. 2001 Mar;3(1):55-62. [PubMed:11250795 ]
  13. Nakamura J, Koh N, Sakakibara F, Hamada Y, Wakao T, Sasaki H, Mori K, Nakashima E, Naruse K, Hotta N: Diabetic neuropathy in sucrose-fed Otsuka Long-Evans Tokushima fatty rats: effect of an aldose reductase inhibitor, TAT. Life Sci. 1997;60(21):1847-57. [PubMed:9154994 ]
  14. Blakemore SJ, Aledo JC, James J, Campbell FC, Lucocq JM, Hundal HS: The GLUT5 hexose transporter is also localized to the basolateral membrane of the human jejunum. Biochem J. 1995 Jul 1;309 ( Pt 1):7-12. [PubMed:7619085 ]
  15. Abou El Fadil-Nicol F, Berger F, Descroix-Vagne M, Pansu D: Presence of sorbin in human digestive tract and endocrine digestive tumours. Gut. 2000 Feb;46(2):182-90. [PubMed:10644311 ]
  16. Faeh D, Minehira K, Schwarz JM, Periasamy R, Park S, Tappy L: Effect of fructose overfeeding and fish oil administration on hepatic de novo lipogenesis and insulin sensitivity in healthy men. Diabetes. 2005 Jul;54(7):1907-13. [PubMed:15983189 ]
  17. Atsumi T, Chesney J, Metz C, Leng L, Donnelly S, Makita Z, Mitchell R, Bucala R: High expression of inducible 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase (iPFK-2; PFKFB3) in human cancers. Cancer Res. 2002 Oct 15;62(20):5881-7. [PubMed:12384552 ]
  18. Wu LY, Juan CC, Hwang LS, Hsu YP, Ho PH, Ho LT: Green tea supplementation ameliorates insulin resistance and increases glucose transporter IV content in a fructose-fed rat model. Eur J Nutr. 2004 Apr;43(2):116-24. Epub 2004 Jan 6. [PubMed:15083319 ]
  19. Ludwig M, Vidal A, Diemer T, Pabst W, Failing K, Weidner W: Seminal secretory capacity of the male accessory sex glands in chronic pelvic pain syndrome (CPPS)/chronic prostatitis with special focus on the new prostatitis classification. Eur Urol. 2002 Jul;42(1):24-8. [PubMed:12121725 ]
  20. Massucco P, Mattiello L, Russo I, Traversa M, Doronzo G, Anfossi G, Trovati M: High glucose rapidly activates the nitric oxide/cyclic nucleotide pathway in human platelets via an osmotic mechanism. Thromb Haemost. 2005 Mar;93(3):517-26. [PubMed:15735804 ]
  21. Sugisawa T, Miyazaki T, Hoshino T: Microbial production of L-ascorbic acid from D-sorbitol, L-sorbose, L-gulose, and L-sorbosone by Ketogulonicigenium vulgare DSM 4025. Biosci Biotechnol Biochem. 2005 Mar;69(3):659-62. doi: 10.1271/bbb.69.659. [PubMed:15785002 ]

Enzymes

General function:
Involved in zinc ion binding
Specific function:
Converts sorbitol to fructose. Part of the polyol pathway that plays an important role in sperm physiology. May play a role in the sperm motility by providing an energetic source for sperm (By similarity).
Gene Name:
SORD
Uniprot ID:
Q00796
Molecular weight:
38324.25
Reactions
L-Iditol + NAD → L-Sorbose + NADHdetails