Canmetcon
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00137
NameTrehalose 6-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionTrehalose 6-phosphate is a substrate for hexokinase (type I) and tryptase beta-1. It is an intermediate in trehalose synthesis pathway. Trehalose is a disaccharide that is ubiquitous in the biosphere. It consists of two subunits of glucose bound by an alpha:1-1 linkage (alpha-D-glucopyranosil alpha-D-glucopyranoside) and is thus nonreducing. Trehalose has been isolated and characterized from many prokaryotic and eukaryotic organisms, including bacteria, yeast, plants, insects and mammals. [Biocyc TRESYN-PWY]
Structure
Thumb
Synonyms
  • alpha-D-glucopyranosyl alpha-D-glucopyranoside 6-(dihydrogen phosphate)
  • alpha,alpha'-Trehalose 6-phosphate
  • Trehalose 6-phosphate
  • Trehalose 6-phosphic acid
  • Trehalose-6-phosphate
  • a,Alpha'-trehalose 6-phosphate
  • a,Alpha'-trehalose 6-phosphoric acid
  • alpha,Alpha'-trehalose 6-phosphoric acid
  • Α,alpha'-trehalose 6-phosphate
  • Α,alpha'-trehalose 6-phosphoric acid
  • a-D-Glucopyranosyl a-D-glucopyranoside 6-(dihydrogen phosphate)
  • a-D-Glucopyranosyl a-D-glucopyranoside 6-(dihydrogen phosphoric acid)
  • alpha-D-Glucopyranosyl alpha-D-glucopyranoside 6-(dihydrogen phosphoric acid)
  • Α-D-glucopyranosyl α-D-glucopyranoside 6-(dihydrogen phosphate)
  • Α-D-glucopyranosyl α-D-glucopyranoside 6-(dihydrogen phosphoric acid)
  • Trehalose 6-phosphoric acid
CAS number4484-88-2
WeightAverage: 422.2764
Monoisotopic: 422.082541956
InChI KeyLABSPYBHMPDTEL-LIZSDCNHSA-N
InChIInChI=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
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 IUPAC Nameα,α'-trehalose 6-phosphate
Chemical FormulaC12H23O14P
SMILES[H]OC([H])([H])[C@@]1([H])O[C@]([H])(O[C@@]2([H])O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Polarizability35.56 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Starch and sucrose metabolismPW002481 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Starch and sucrose metabolismec00500 Map00500
SMPDB Reactions
Uridine diphosphate glucose + alpha-D-glucose 6 phosphateUridine 5'-diphosphate + Trehalose 6-phosphate
Trehalose 6-phosphate + waterTrehalose + phosphate
KEGG Reactions
aldehydo-D-glucose 6-phosphate + Uridine diphosphate glucoseUridine 5'-diphosphate + hydron + Trehalose 6-phosphate
water + Trehalose 6-phosphatephosphate + Trehalose
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Blazquez, M. A., Lagunas, R., Gancedo, C., Gancedo, J. M. (1993). "Trehalose-6-phosphate, a new regulator of yeast glycolysis that inhibits hexokinases." FEBS Lett 329:51-54.8354408
  • De Virgilio, C., Burckert, N., Bell, W., Jeno, P., Boller, T., Wiemken, A. (1993). "Disruption of TPS2, the gene encoding the 100-kDa subunit of the trehalose-6-phosphate synthase/phosphatase complex in Saccharomyces cerevisiae, causes accumulation of trehalose-6-phosphate and loss of trehalose-6-phosphate phosphatase activity." Eur J Biochem 212:315-323.8444170
Synthesis Reference:MacDonald, Donald L.; Wong, Roger Y. K. Chemical synthesis of trehalose 6-phosphate. Biochimica et Biophysica Acta, General Subjects (1964), 86(2), 390-2.
External Links:
ResourceLink
CHEBI ID18283
HMDB IDHMDB01124
Pubchem Compound ID122336
Kegg IDC00689
ChemSpider ID24785573
FOODB IDFDB022437
Wikipedia IDNot Available
BioCyc IDTREHALOSE-6P

Enzymes

General function:
Involved in catalytic activity
Specific function:
Phosphatase catalytic subunit of the trehalose synthase complex that catalyzes the production of trehalose from glucose-6- phosphate and UDP-glucose in a two step process
Gene Name:
TPS2
Uniprot ID:
P31688
Molecular weight:
102976.0
Reactions
Trehalose 6-phosphate + H(2)O → trehalose + phosphate.
General function:
Involved in catalytic activity
Specific function:
Synthase catalytic subunit of the trehalose synthase complex that catalyzes the production of trehalose from glucose-6- phosphate and UDP-glucose in a two step process. Can function independently of the complex
Gene Name:
TPS1
Uniprot ID:
Q00764
Molecular weight:
56147.5
Reactions
UDP-glucose + D-glucose 6-phosphate → UDP + alpha,alpha-trehalose 6-phosphate.
General function:
Involved in catalytic activity
Specific function:
Regulatory subunit of the trehalose synthase complex that catalyzes the production of trehalose from glucose-6- phosphate and UDP-glucose in a two step process. May stabilize the trehalose synthase complex
Gene Name:
TPS3
Uniprot ID:
P38426
Molecular weight:
118834.0
Reactions