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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-05-24 16:23:24 UTC
HMDB IDHMDB0000975
Secondary Accession Numbers
  • HMDB00975
Metabolite Identification
Common NameTrehalose
DescriptionTrehalose, also known as mycose, is a 1-alpha (disaccharide) sugar found extensively but not abundantly in nature. It is thought to be implicated in anhydrobiosis - the ability of plants and animals to withstand prolonged periods of desiccation. The sugar is thought to form a gel phase as cells dehydrate, which prevents disruption of internal cell organelles by effectively splinting them in position. Rehydration then allows normal cellular activity to be resumed without the major, generally lethal damage that would normally follow a dehydration/reyhdration cycle. Trehalose is a non-reducing sugar formed from two glucose units joined by a 1-1 alpha bond giving it the name of alpha-D-glucopyranoglucopyranosyl-1,1-alpha-D-glucopyranoside. The bonding makes trehalose very resistant to acid hydrolysis, and therefore stable in solution at high temperatures even under acidic conditions. The bonding also keeps non-reducing sugars in closed-ring form, such that the aldehyde or ketone end-groups do not bind to the lysine or arginine residues of proteins (a process called glycation). The enzyme trehalase, present but not abundant in most people, breaks it into two glucose molecules, which can then be readily absorbed in the gut. Trehalose is an important components of insects circulating fluid. It acts as a storage form of insect circulating fluid and it is important in respiration. Trehalose has also been found to be a metabolite of Burkholderia, Escherichia and Propionibacterium (PMID: 12105274 ; PMID: 25479689 ) (krishikosh.egranth.ac.in/bitstream/1/84382/1/88571%20P-1257.pdf).
Structure
Data?1558715004
Synonyms
ValueSource
(GLC)2ChEBI
alpha,Alpha'-trehaloseChEBI
alpha-D-GLCP-(11)-alpha-D-GLCPChEBI
alpha-D-Glucopyranosyl-alpha-D-glucopyranosideChEBI
alpha-D-TrehaloseChEBI
alpha-TrehaloseChEBI
D-(+)-TrehaloseChEBI
Ergot sugarChEBI
MycoseChEBI
a,Alpha'-trehaloseGenerator
Α,alpha'-trehaloseGenerator
a-D-GLCP-(11)-a-D-GLCPGenerator
Α-D-GLCP-(11)-α-D-GLCPGenerator
a-D-Glucopyranosyl-a-D-glucopyranosideGenerator
Α-D-glucopyranosyl-α-D-glucopyranosideGenerator
a-D-TrehaloseGenerator
Α-D-trehaloseGenerator
a-TrehaloseGenerator
Α-trehaloseGenerator
alpha,alpha-TrehaloseHMDB
D-Trehalose-anhydrousHMDB
delta-Trehalose-anhydrousHMDB
D-TrehaloseHMDB
Natural trehaloseHMDB
O-D-Glucopyranosyl-(1→1)-D-glucopyranosideHMDB
TrehaloseHMDB
alpha,alpha'-D-TrehaloseHMDB
alpha-D-Glucopyranosyl alpha-D-glucopyranosideHMDB
α,α'-D-TrehaloseHMDB
α,α-TrehaloseHMDB
α,α’-D-TrehaloseHMDB
α-D-Glucopyranosyl α-D-glucopyranosideHMDB
Chemical FormulaC12H22O11
Average Molecular Weight342.2965
Monoisotopic Molecular Weight342.116211546
IUPAC Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-3,4,5-triol
Traditional Nameα,α'-trehalose
CAS Registry Number99-20-7
SMILES
[H][C@]1(O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C12H22O11/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1
InChI KeyHDTRYLNUVZCQOY-LIZSDCNHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • Oxane
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • 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:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point203 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility592 g/LALOGPS
logP-3ALOGPS
logP-4.7ChemAxon
logS0.24ALOGPS
pKa (Strongest Acidic)11.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.34 m³·mol⁻¹ChemAxon
Polarizability31.14 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0j4m-0932000000-8d7c80edd7f55e92ea29JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-9511000000-b710c7c4bd86fd5f1af0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-9511000000-2e5f22e6ba282283a569JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-9832000000-b3259de2e25ea7293565JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0wos-0921000000-68fb82f427417ec703a0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0j4m-0943000000-07c11d483e4278dc639aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0wmm-0953000000-b74403fa3ce6ce0339ebJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0i04-0932000000-8de0421184ae3291ea53JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-8932000000-c327fe31b8d3e86dd97dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (8 TMS)splash10-0j4l-0954000000-33e230d28780be607983JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0j4m-0932000000-8d7c80edd7f55e92ea29JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9511000000-b710c7c4bd86fd5f1af0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9511000000-2e5f22e6ba282283a569JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9832000000-b3259de2e25ea7293565JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0wos-0921000000-68fb82f427417ec703a0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0j4m-0943000000-07c11d483e4278dc639aJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0wmm-0953000000-b74403fa3ce6ce0339ebJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0i04-0932000000-8de0421184ae3291ea53JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-8932000000-c327fe31b8d3e86dd97dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0j4l-0954000000-33e230d28780be607983JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0i2d-0921000000-9e633378baf1645df2a1JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08ni-9554000000-e418bec346785e269084JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-2553419000-dd0bea0ade3ee46308dcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-1901000000-865e9e390fac7d13c2f8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9500000000-7d4c9de285c2872d2320JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-c71f25d08b875caff6b6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0006-0019000000-3b4e276ff5686c841bddJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0fdx-8905000000-fafde7828ce0d63fe618JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fdx-8905000000-f4b4b3ad528ea3bf43c2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-0900000000-d382926500274fb84a46JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-10524d7a715f8a0ed265JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0019000000-3b4e276ff5686c841bddJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ec-0903000000-8981579ae1dd58ba65c9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1901000000-4c8ec381daa00b88a539JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-5900000000-89485b49a32afa256bdcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-4918000000-df3152da1740bcb45d3dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03mi-3901000000-c9e67703b1ef9ca4f8ccJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9600000000-b9d2971c377f79dd6238JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-022c-9100000000-33d1067ccb0cb2dda51dJSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Feces
  • Urine
Tissue Locations
  • Epidermis
  • Fibroblasts
  • Kidney
  • Muscle
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
UrineDetected and Quantified5.298 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Mordechai, Hien, ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Not SpecifiedNot Specified
Cryptosporidium infection
details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12310
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001114
KNApSAcK IDC00001152
Chemspider ID7149
KEGG Compound IDC01083
BioCyc IDTREHALOSE
BiGG ID36774
Wikipedia LinkTrehalose
METLIN ID5913
PubChem Compound7427
PDB IDNot Available
ChEBI ID16551
References
Synthesis ReferenceMurao, Sawao; Nagano, Hiroto; Ogura, Sei; Nishino, Toyokazu. Enzymic synthesis of trehalose from maltose. Agricultural and Biological Chemistry (1985), 49(7), 2113-18.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Kandror O, DeLeon A, Goldberg AL: Trehalose synthesis is induced upon exposure of Escherichia coli to cold and is essential for viability at low temperatures. Proc Natl Acad Sci U S A. 2002 Jul 23;99(15):9727-32. Epub 2002 Jul 8. [PubMed:12105274 ]
  2. Potier M, Dallaire L, Melancon SB: Occurrence and properties of fetal intestinal glycosidases (disaccharidases) in human amniotic fluid. Biol Neonate. 1975;27(3-4):141-52. [PubMed:241430 ]
  3. Citron DM, Baron EJ, Finegold SM, Goldstein EJ: Short prereduced anaerobically sterilized (PRAS) biochemical scheme for identification of clinical isolates of bile-resistant Bacteroides species. J Clin Microbiol. 1990 Oct;28(10):2220-3. [PubMed:2229345 ]
  4. Yoshioka S, Aso Y: A quantitative assessment of the significance of molecular mobility as a determinant for the stability of lyophilized insulin formulations. Pharm Res. 2005 Aug;22(8):1358-64. Epub 2005 Aug 3. [PubMed:16078146 ]
  5. Guo N, Puhlev I, Brown DR, Mansbridge J, Levine F: Trehalose expression confers desiccation tolerance on human cells. Nat Biotechnol. 2000 Feb;18(2):168-71. [PubMed:10657122 ]
  6. Nie Y, de Pablo JJ, Palecek SP: Platelet cryopreservation using a trehalose and phosphate formulation. Biotechnol Bioeng. 2005 Oct 5;92(1):79-90. [PubMed:15937943 ]
  7. Fujita Y, Naka T, Doi T, Yano I: Direct molecular mass determination of trehalose monomycolate from 11 species of mycobacteria by MALDI-TOF mass spectrometry. Microbiology. 2005 May;151(Pt 5):1443-52. [PubMed:15870454 ]
  8. Lu FQ, Liu JH, Ouyang XL, Li XJ, Zhou J, Zhuang Y: [Process of human platelets loaded with rehalose before lyophilization]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2006 Feb;14(1):156-61. [PubMed:16584614 ]
  9. Shirkhanzadeh M: Microneedles coated with porous calcium phosphate ceramics: effective vehicles for transdermal delivery of solid trehalose. J Mater Sci Mater Med. 2005 Jan;16(1):37-45. [PubMed:15754142 ]
  10. Eroglu A, Russo MJ, Bieganski R, Fowler A, Cheley S, Bayley H, Toner M: Intracellular trehalose improves the survival of cryopreserved mammalian cells. Nat Biotechnol. 2000 Feb;18(2):163-7. [PubMed:10657121 ]
  11. Arguelles JC, Rodriguez T, Alvarez-Peral FJ: Trehalose hydrolysis is not required for human serum-induced dimorphic transition in Candida albicans: evidence from a tps1/tps1 mutant deficient in trehalose synthesis. Res Microbiol. 1999 Oct;150(8):521-9. [PubMed:10577485 ]
  12. Corning BF, Murphy JC, Fox JG: Group G streptococcal lymphadenitis in rats. J Clin Microbiol. 1991 Dec;29(12):2720-3. [PubMed:1757539 ]
  13. Davies JE, Sarkar S, Rubinsztein DC: Trehalose reduces aggregate formation and delays pathology in a transgenic mouse model of oculopharyngeal muscular dystrophy. Hum Mol Genet. 2006 Jan 1;15(1):23-31. Epub 2005 Nov 25. [PubMed:16311254 ]
  14. Ma X, Jamil K, Macrae TH, Clegg JS, Russell JM, Villeneuve TS, Euloth M, Sun Y, Crowe JH, Tablin F, Oliver AE: A small stress protein acts synergistically with trehalose to confer desiccation tolerance on mammalian cells. Cryobiology. 2005 Aug;51(1):15-28. [PubMed:15963489 ]
  15. Alcoba-Florez J, Mendez-Alvarez S, Cano J, Guarro J, Perez-Roth E, del Pilar Arevalo M: Phenotypic and molecular characterization of Candida nivariensis sp. nov., a possible new opportunistic fungus. J Clin Microbiol. 2005 Aug;43(8):4107-11. [PubMed:16081957 ]
  16. Chang L, Shepherd D, Sun J, Ouellette D, Grant KL, Tang XC, Pikal MJ: Mechanism of protein stabilization by sugars during freeze-drying and storage: native structure preservation, specific interaction, and/or immobilization in a glassy matrix? J Pharm Sci. 2005 Jul;94(7):1427-44. [PubMed:15920775 ]
  17. Sasnoor LM, Kale VP, Limaye LS: A combination of catalase and trehalose as additives to conventional freezing medium results in improved cryoprotection of human hematopoietic cells with reference to in vitro migration and adhesion properties. Transfusion. 2005 Apr;45(4):622-33. [PubMed:15819685 ]
  18. Alvarez-Peral FJ, Arguelles JC: Changes in external trehalase activity during human serum-induced dimorphic transition in Candida albicans. Res Microbiol. 2000 Dec;151(10):837-43. [PubMed:11191809 ]
  19. Berlutti F, Thaller MC, Dainelli B, Pezzi R: T-mod pathway, a reduced sequence for identification of gram-negative urinary tract pathogens. J Clin Microbiol. 1989 Jul;27(7):1646-9. [PubMed:2768451 ]
  20. Habe H, Sato S, Morita T, Fukuoka T, Kirimura K, Kitamoto D: Bacterial production of short-chain organic acids and trehalose from levulinic acid: a potential cellulose-derived building block as a feedstock for microbial production. Bioresour Technol. 2015 Feb;177:381-6. doi: 10.1016/j.biortech.2014.11.048. Epub 2014 Nov 18. [PubMed:25479689 ]

Enzymes

General function:
Involved in catalytic activity
Specific function:
Intestinal trehalase is probably involved in the hydrolysis of ingested trehalose.
Gene Name:
TREH
Uniprot ID:
O43280
Molecular weight:
66567.26
Reactions
Trehalose + Water → beta-D-Glucose + alpha-D-Glucosedetails
Trehalose + Water → D-Glucosedetails