You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:17 UTC
HMDB IDHMDB01328
Secondary Accession NumbersNone
Metabolite Identification
Common NamedTDP-D-glucose
DescriptionDeoxythymidine diphosphate-glucose is an intermediate in the nucleotide sugar metabolism pathway (KEGG). It is a substrate for the enzyme dTDP-D-glucose 4,6-dehydratase which catalyzes the reaction: dTDP-glucose = dTDP-4-dehydro-6-deoxy-D-glucose + H2O.
Structure
Thumb
Synonyms
ValueSource
dTDP-delta-GlucoseHMDB
dTDP-GlucoseHMDB
DTDPglucoseHMDB
mono-a-D-Glucopyranosyl esterHMDB
mono-alpha-D-Glucopyranosyl esterHMDB
mono-alpha-delta-Glucopyranosyl esterHMDB
TDP-D-GlucoseHMDB
TDP-delta-GlucoseHMDB
TDP-GLCHMDB
TDPGHMDB
Thymidine 5-diphosphate-D-glucoseHMDB
Thymidine 5-diphosphate-delta-glucoseHMDB
Chemical FormulaC16H26N2O16P2
Average Molecular Weight564.329
Monoisotopic Molecular Weight564.075755818
IUPAC Name{[hydroxy({[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy}({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid
Traditional Namedtdp-D-glucose
CAS Registry Number2196-62-5
SMILES
CC1=CN([C@H]2C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)O2)C(=O)NC1=O
InChI Identifier
InChI=1S/C16H26N2O16P2/c1-6-3-18(16(25)17-14(6)24)10-2-7(20)9(31-10)5-30-35(26,27)34-36(28,29)33-15-13(23)12(22)11(21)8(4-19)32-15/h3,7-13,15,19-23H,2,4-5H2,1H3,(H,26,27)(H,28,29)(H,17,24,25)/t7-,8+,9+,10+,11+,12-,13+,15?/m0/s1
InChI KeyInChIKey=YSYKRGRSMLTJNL-KFQCIAAJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleotides
Sub ClassPyrimidine nucleotide sugars
Direct ParentPyrimidine nucleotide sugars
Alternative Parents
Substituents
  • Pyrimidine nucleotide sugar
  • Pyrimidine 2'-deoxyribonucleoside diphosphate
  • Pyrimidine deoxyribonucleotide
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Pyrimidone
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Hydropyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Oxolane
  • Urea
  • Secondary alcohol
  • Polyol
  • Lactam
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Nucleotide sugars metabolism
  • Component of Polyketide sugar unit biosynthesis
  • Component of Streptomycin biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm (predicted from logP)
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 Solubility11.2 mg/mLALOGPS
logP-1.2ALOGPS
logP-3.7ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area271.31 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity109.3 m3·mol-1ChemAxon
Polarizability46.61 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-312a08522e3cb22b111bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2921000000-d3da9a944bb5a8c62cfbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-4900000000-415f5eced8f6fd67d535View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-1403290000-6b2a8c7a42ac2eaa39c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fbc-4905010000-8e6b9db92566b846a800View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6u-4901000000-4c65036f67c107c3bdf5View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022557
KNApSAcK IDNot Available
Chemspider ID388455
KEGG Compound IDC00842
BioCyc IDDTDP-D-GLUCOSE
BiGG ID36175
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01328
Metagene LinkHMDB01328
METLIN ID6163
PubChem Compound439324
PDB IDNot Available
ChEBI ID35248
References
Synthesis ReferenceGoncalves, Ruth J. Thymidine diphosphate glucose and biosynthesis of glucosides in wheat germ. I. Enzymologia (1963), 26(5), 287-93.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
TGDS
Uniprot ID:
O95455
Molecular weight:
40213.665
Reactions
dTDP-D-glucose → 4,6-Dideoxy-4-oxo-dTDP-D-glucose + Waterdetails
General function:
Involved in catalytic activity
Specific function:
Catalyzes two distinct but analogous reactions: the epimerization of UDP-glucose to UDP-galactose and the epimerization of UDP-N-acetylglucosamine to UDP-N-acetylgalactosamine.
Gene Name:
GALE
Uniprot ID:
Q14376
Molecular weight:
38281.435
Reactions
dTDP-D-glucose → dTDP-D-galactosedetails