Showing metabocard for Trehalose (BMDB0000975)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Show more...Show more...
Record Information
Version1.0
Creation Date2016-09-30 22:39:21 UTC
Update Date2020-05-21 16:29:07 UTC
BMDB IDBMDB0000975
Secondary Accession Numbers
  • BMDB00975
Metabolite Identification
Common NameTrehalose
DescriptionTrehalose, also known as alpha-D-trehalose or (GLC)2, 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. Trehalose exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Trehalose exists in all living species, ranging from bacteria to humans. Trehalose can be converted into Beta-D-glucose and Alpha-D-glucose; which is mediated by the enzyme trehalase. In cattle, trehalose is involved in the metabolic pathway called the trehalose degradation pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
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
OC[C@H]1O[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[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
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point203 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0j4m-0932000000-8d7c80edd7f55e92ea29View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-9511000000-b710c7c4bd86fd5f1af0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-9511000000-2e5f22e6ba282283a569View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-9832000000-b3259de2e25ea7293565View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0wos-0921000000-68fb82f427417ec703a0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0j4m-0943000000-07c11d483e4278dc639aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-0wmm-0953000000-b74403fa3ce6ce0339ebView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0i04-0932000000-8de0421184ae3291ea53View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (8 TMS)splash10-00di-8932000000-c327fe31b8d3e86dd97dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (8 TMS)splash10-0j4l-0954000000-33e230d28780be607983View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0j4m-0932000000-8d7c80edd7f55e92ea29View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9511000000-b710c7c4bd86fd5f1af0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9511000000-2e5f22e6ba282283a569View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9832000000-b3259de2e25ea7293565View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0wos-0921000000-68fb82f427417ec703a0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0j4m-0943000000-07c11d483e4278dc639aView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0wmm-0953000000-b74403fa3ce6ce0339ebView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0i04-0932000000-8de0421184ae3291ea53View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-8932000000-c327fe31b8d3e86dd97dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0j4l-0954000000-33e230d28780be607983View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0i2d-0921000000-9e633378baf1645df2a1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08ni-9554000000-e418bec346785e269084View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-2553419000-dd0bea0ade3ee46308dcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-1901000000-865e9e390fac7d13c2f8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9500000000-7d4c9de285c2872d2320View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-c71f25d08b875caff6b6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0006-0019000000-3b4e276ff5686c841bddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0fdx-8905000000-fafde7828ce0d63fe618View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fdx-8905000000-f4b4b3ad528ea3bf43c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-0900000000-d382926500274fb84a46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-10524d7a715f8a0ed265View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0019000000-3b4e276ff5686c841bddView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-9ae5587f61124e19e967View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-052r-9400000000-912468a68a25ec147569View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0926000000-b1b3f8b4fbacdcc1180fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9200000000-0088f187ae8b6d9b5c2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9200000000-8437afa67780c28771b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-5809000000-5a5cec80f792fdde61bbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0900000000-c4415a0eb58b8c1c5640View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0926000000-af9f579519c642acb94fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-9300000000-197e82f358194cd04b3cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01q9-3593000000-97d3b3b35a65f632fdddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ec-0903000000-8981579ae1dd58ba65c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1901000000-4c8ec381daa00b88a539View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-5900000000-89485b49a32afa256bdcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-4918000000-df3152da1740bcb45d3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03mi-3901000000-c9e67703b1ef9ca4f8ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9600000000-b9d2971c377f79dd6238View in MoNA
MSMass Spectrum (Electron Ionization)splash10-022c-9100000000-33d1067ccb0cb2dda51dView in MoNA
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Epidermis
  • Fibroblasts
  • Kidney
  • Liver
  • Mammary Gland
  • Platelet
  • Skeletal Muscle
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
HMDB IDHMDB0000975
DrugBank IDDB12310
Phenol Explorer Compound IDNot Available
FooDB 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)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Trehalase
General function:
Not Available
Specific function:
Not Available
Gene Name:
TREH
Uniprot ID:
E1B8N4
Molecular weight:
65887.0
Reactions
Trehalose + Water → Beta-D-Glucose + Alpha-D-Glucosedetails