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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-03-13 16:37:49 UTC
HMDB IDHMDB0001124
Secondary Accession Numbers
  • HMDB01124
Metabolite Identification
Common NameTrehalose 6-phosphate
DescriptionTrehalose 6-phosphate belongs to the class of organic compounds known as disaccharide phosphates. These are disaccharides carrying one or more phosphate group on a sugar unit. Trehalose 6-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Trehalose 6-phosphate exists in all living species, ranging from bacteria to humans. Outside of the human body, Trehalose 6-phosphate has been detected, but not quantified in, several different foods, such as komatsuna, cereals and cereal products, passion fruits, biscuits, and pepper (c. frutescens). This could make trehalose 6-phosphate a potential biomarker for the consumption of these foods. Trehalose 6-phosphate is a substrate for Hexokinase (type I) and Tryptase beta-1.
Structure
Data?1584117468
Synonyms
ValueSource
alpha,Alpha'-trehalose 6-phosphateChEBI
alpha-D-Glucopyranosyl alpha-D-glucopyranoside 6-(dihydrogen phosphate)ChEBI
a,Alpha'-trehalose 6-phosphateGenerator
a,Alpha'-trehalose 6-phosphoric acidGenerator
alpha,Alpha'-trehalose 6-phosphoric acidGenerator
Α,alpha'-trehalose 6-phosphateGenerator
Α,alpha'-trehalose 6-phosphoric acidGenerator
a-D-Glucopyranosyl a-D-glucopyranoside 6-(dihydrogen phosphate)Generator
a-D-Glucopyranosyl a-D-glucopyranoside 6-(dihydrogen phosphoric acid)Generator
alpha-D-Glucopyranosyl alpha-D-glucopyranoside 6-(dihydrogen phosphoric acid)Generator
Α-D-glucopyranosyl α-D-glucopyranoside 6-(dihydrogen phosphate)Generator
Α-D-glucopyranosyl α-D-glucopyranoside 6-(dihydrogen phosphoric acid)Generator
Trehalose 6-phosphoric acidGenerator
Trehalose-6-phosphateHMDB
Chemical FormulaC12H23O14P
Average Molecular Weight422.2764
Monoisotopic Molecular Weight422.082541956
IUPAC Name{[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}phosphonic acid
Traditional Nameα,α'-trehalose 6-phosphate
CAS Registry Number4484-88-2
SMILES
OC[C@H]1O[C@H](O[C@H]2O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C12H23O14P/c13-1-3-5(14)7(16)9(18)11(24-3)26-12-10(19)8(17)6(15)4(25-12)2-23-27(20,21)22/h3-19H,1-2H2,(H2,20,21,22)/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1
InChI KeyLABSPYBHMPDTEL-LIZSDCNHSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as disaccharide phosphates. These are disaccharides carrying one or more phosphate group on a sugar unit.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentDisaccharide phosphates
Alternative Parents
Substituents
  • Disaccharide phosphate
  • Glycosyl compound
  • O-glycosyl compound
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Acetal
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility40.6 g/LALOGPS
logP-2.4ALOGPS
logP-4.8ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area236.06 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity79.21 m³·mol⁻¹ChemAxon
Polarizability35.55 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01dj-0953000000-810c820781c23288e479Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01dj-0953000000-810c820781c23288e479Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0nmm-8936500000-17d0f10b6e49a9f3beb2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-3541019000-4babdd6642f68fe53628Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0000900000-6dde54156ac4b17c4db3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0000900000-bdea675d4ffc4fb1386cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-1020900000-22ce67be497ade27ed91Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004m-9130000000-29a3d6b109480b5fa838Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-e2a394714155764b8b6cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03k9-0901500000-7be01f5512eb80cbc27fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-a71a48d6d2284f9960ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-9330908b737811ce7bd5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-01t9-1900000000-392ddfdf3f2c8240f176Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-003r-7900000000-6d514ff26629cdefdae4Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-03di-0190600000-bd05da78e082c65e54e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0950200000-892f27ada42528b88923Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-1940000000-562cf60e2df9ae537d3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2900000000-80b677accd914bdf5cdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05di-9540400000-a224ab96a48be27b9eb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9210000000-bc2b2577f83fa445d854Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-0024eb099e0b2c51e332Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02430
Phenol Explorer Compound IDNot Available
FooDB IDFDB022437
KNApSAcK IDC00007451
Chemspider ID109086
KEGG Compound IDC00689
BioCyc IDTREHALOSE-6P
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6019
PubChem Compound122336
PDB IDNot Available
ChEBI ID18283
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceMacDonald, Donald L.; Wong, Roger Y. K. Chemical synthesis of trehalose 6-phosphate. Biochimica et Biophysica Acta, General Subjects (1964), 86(2), 390-2.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available