Record Information
Version1.0
Creation date2015-05-07 21:21:19 UTC
Update date2020-09-17 15:38:45 UTC
Primary IDFDB031220
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon. Trehalose is an extremely weak basic (essentially neutral) compound (based on its pKa). Trehalose exists in all living species, ranging from bacteria to humans. trehalose can be converted into β-D-glucose and α-D-glucose; which is mediated by the enzyme trehalase. In humans, trehalose is involved in trehalose degradation. Outside of the human body, Trehalose has been detected, but not quantified in, a few different foods, such as bitter gourds, garden tomato, and mushrooms. This could make trehalose a potential biomarker for the consumption of these foods.
CAS Number99-20-7
Structure
Thumb
Synonyms
SynonymSource
(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
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
TrehaloseHMDB
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H22O11
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
InChI IdentifierInChI=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
Isomeric SMILESOC[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
Average Molecular Weight342.2965
Monoisotopic Molecular Weight342.116211546
Classification
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:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-022c-9100000000-33d1067ccb0cb2dda51d2018-05-25View Spectrum
GC-MStrehalose, 8 TMS, GC-MS Spectrumsplash10-0j4m-0932000000-8d7c80edd7f55e92ea29Spectrum
GC-MStrehalose, 8 TMS, GC-MS Spectrumsplash10-00di-9511000000-b710c7c4bd86fd5f1af0Spectrum
GC-MStrehalose, 8 TMS, GC-MS Spectrumsplash10-00di-9511000000-2e5f22e6ba282283a569Spectrum
GC-MStrehalose, 8 TMS, GC-MS Spectrumsplash10-00di-9832000000-b3259de2e25ea7293565Spectrum
GC-MStrehalose, 8 TMS, GC-MS Spectrumsplash10-0wos-0921000000-68fb82f427417ec703a0Spectrum
GC-MStrehalose, 8 TMS, GC-MS Spectrumsplash10-0j4m-0943000000-07c11d483e4278dc639aSpectrum
GC-MStrehalose, 8 TMS, GC-MS Spectrumsplash10-0wmm-0953000000-b74403fa3ce6ce0339ebSpectrum
GC-MStrehalose, non-derivatized, GC-MS Spectrumsplash10-0i04-0932000000-8de0421184ae3291ea53Spectrum
GC-MStrehalose, 8 TMS, GC-MS Spectrumsplash10-00di-8932000000-c327fe31b8d3e86dd97dSpectrum
GC-MStrehalose, 8 TMS, GC-MS Spectrumsplash10-0j4l-0954000000-33e230d28780be607983Spectrum
GC-MStrehalose, non-derivatized, GC-MS Spectrumsplash10-0j4m-0932000000-8d7c80edd7f55e92ea29Spectrum
GC-MStrehalose, non-derivatized, GC-MS Spectrumsplash10-00di-9511000000-b710c7c4bd86fd5f1af0Spectrum
GC-MStrehalose, non-derivatized, GC-MS Spectrumsplash10-00di-9511000000-2e5f22e6ba282283a569Spectrum
GC-MStrehalose, non-derivatized, GC-MS Spectrumsplash10-00di-9832000000-b3259de2e25ea7293565Spectrum
GC-MStrehalose, non-derivatized, GC-MS Spectrumsplash10-0wos-0921000000-68fb82f427417ec703a0Spectrum
GC-MStrehalose, non-derivatized, GC-MS Spectrumsplash10-0j4m-0943000000-07c11d483e4278dc639aSpectrum
GC-MStrehalose, non-derivatized, GC-MS Spectrumsplash10-0wmm-0953000000-b74403fa3ce6ce0339ebSpectrum
GC-MStrehalose, non-derivatized, GC-MS Spectrumsplash10-0i04-0932000000-8de0421184ae3291ea53Spectrum
GC-MStrehalose, non-derivatized, GC-MS Spectrumsplash10-00di-8932000000-c327fe31b8d3e86dd97dSpectrum
GC-MStrehalose, non-derivatized, GC-MS Spectrumsplash10-0j4l-0954000000-33e230d28780be607983Spectrum
GC-MStrehalose, non-derivatized, GC-MS Spectrumsplash10-0i2d-0921000000-9e633378baf1645df2a1Spectrum
Predicted GC-MStrehalose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08ni-9554000000-e418bec346785e269084Spectrum
Predicted GC-MStrehalose, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-2553419000-dd0bea0ade3ee46308dcSpectrum
Predicted GC-MStrehalose, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MStrehalose, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-1901000000-865e9e390fac7d13c2f82012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9500000000-7d4c9de285c2872d23202012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-c71f25d08b875caff6b62012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0006-0019000000-3b4e276ff5686c841bdd2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0fdx-8905000000-fafde7828ce0d63fe6182012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0fdx-8905000000-f4b4b3ad528ea3bf43c22017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-0900000000-d382926500274fb84a462017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0udi-0090000000-10524d7a715f8a0ed2652017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0006-0019000000-3b4e276ff5686c841bdd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-9ae5587f61124e19e9672021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-052r-9400000000-912468a68a25ec1475692021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0926000000-b1b3f8b4fbacdcc1180f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9200000000-0088f187ae8b6d9b5c2e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9200000000-8437afa67780c28771b82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-5809000000-5a5cec80f792fdde61bb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0900000000-c4415a0eb58b8c1c56402021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0926000000-af9f579519c642acb94f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-9300000000-197e82f358194cd04b3c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01q9-3593000000-97d3b3b35a65f632fddd2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ec-0903000000-8981579ae1dd58ba65c92016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1901000000-4c8ec381daa00b88a5392016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-5900000000-89485b49a32afa256bdc2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-4918000000-df3152da1740bcb45d3d2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03mi-3901000000-c9e67703b1ef9ca4f8cc2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002f-9600000000-b9d2971c377f79dd62382016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
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)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference