Record Information
Version2.0
Creation Date2012-05-31 13:49:58 -0600
Update Date2015-09-13 15:15:22 -0600
Secondary Accession Numbers
  • ECMDB01328
Identification
Name:dTDP-D-Glucose
DescriptiondTDP-D-glucose is a member of the chemical class known as Pyrimidine Nucleotide Sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. dTDP-D-glucose is a key metabolite in prokaryotes as a precursor for a large number of modified deoxysugars, and these deoxysugars are a major part of various antibiotics, ranging from glycosides to macrolides. (PMID 18051285)
Structure
Thumb
Synonyms:
  • DTDP-D-Glucose
  • DTDP-delta-glucose
  • DTDP-Glc
  • DTDP-Glucose
  • dTDP-δ-Glucose
  • DTDPglucose
  • Mono-a-D-glucopyranosyl ester
  • mono-a-delta-Glucopyranosyl ester
  • mono-a-δ-Glucopyranosyl ester
  • Mono-alpha-D-glucopyranosyl ester
  • Mono-alpha-delta-glucopyranosyl ester
  • mono-α-D-Glucopyranosyl ester
  • mono-α-δ-Glucopyranosyl ester
  • P-a-D-Glucopyranosyl ester
  • P-alpha-D-Glucopyranosyl ester
  • P-α-D-Glucopyranosyl ester
  • TDP-D-Glucose
  • TDP-delta-glucose
  • TDP-Glc
  • TDP-Glucose
  • TDP-δ-Glucose
  • TDPG
  • Thymidine 5-(trihydrogen diphosphate)
  • Thymidine 5-(trihydrogen diphosphoric acid)
  • Thymidine 5-diphosphate-D-Glucose
  • Thymidine 5-diphosphate-delta-Glucose
  • Thymidine 5-diphosphate-δ-glucose
  • Thymidine 5-diphosphoric acid-D-glucose
  • Thymidine 5-diphosphoric acid-delta-glucose
  • Thymidine 5-diphosphoric acid-δ-glucose
Chemical Formula:C16H26N2O16P2
Weight:Average: 564.329
Monoisotopic: 564.075755818
InChI Key:YSYKRGRSMLTJNL-KFQCIAAJSA-N
InChI: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
CAS number:2196-62-5
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 IUPAC Name:dtdp-D-glucose
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
Chemical Taxonomy
Description 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
  • Pentose phosphate
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Pyrimidone
  • Hydropyrimidine
  • Phosphoric acid ester
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Oxane
  • Alkyl phosphate
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Urea
  • Lactam
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Polyol
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:-5.568PhysProp
Predicted Properties
PropertyValueSource
Water Solubility11.2 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity109.3 m³·mol⁻¹ChemAxon
Polarizability46.61 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
O-antigen building blocks biosynthesisPW002089 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: enterobacterial common antigen biosynthesisPW000959 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: enterobacterial common antigen biosynthesis 2PW002045 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW000941 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054p-7920560000-231b6626719eee6c053eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0600-9411517000-1aaf284fc97b157c78d4View in MoNA
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
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Han, J. M., Kim, S. M., Lee, H. J., Yoo, J. C. (2007). "Cloning and expression of glucose-1-phosphate thymidylyltransferase gene (schS6) from Streptomyces sp. SCC-2136." J Microbiol Biotechnol 17:685-690. Pubmed: 18051285
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Goncalves, 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
External Links:
ResourceLink
CHEBI ID15700
HMDB IDHMDB01328
Pubchem Compound ID439324
Kegg IDC00842
ChemSpider ID388455
Wikipedia IDNot Available
BioCyc IDDTDP-D-GLUCOSE
EcoCyc IDDTDP-D-GLUCOSE

Enzymes

General function:
Involved in catalytic activity
Specific function:
UDP-glucose = UDP-galactose
Gene Name:
galE
Uniprot ID:
P09147
Molecular weight:
37265
Reactions
UDP-glucose = UDP-galactose.
General function:
Involved in dTDP-glucose 4,6-dehydratase activity
Specific function:
Catalyzes the dehydration of dTDP-D-glucose to form dTDP-6-deoxy-D-xylo-4-hexulose via a three-step process involving oxidation, dehydration and reduction
Gene Name:
rffG
Uniprot ID:
P27830
Molecular weight:
39754
Reactions
dTDP-glucose = dTDP-4-dehydro-6-deoxy-D-glucose + H(2)O.
General function:
Involved in glucose-1-phosphate thymidylyltransferase activity
Specific function:
Catalyzes the formation of dTDP-glucose, from dTTP and glucose 1-phosphate, as well as its pyrophosphorolysis
Gene Name:
rmlA1
Uniprot ID:
P37744
Molecular weight:
32693
Reactions
dTTP + alpha-D-glucose 1-phosphate = diphosphate + dTDP-glucose.
General function:
Involved in dTDP-glucose 4,6-dehydratase activity
Specific function:
Catalyzes the dehydration of dTDP-D-glucose to form dTDP-6-deoxy-D-xylo-4-hexulose via a three-step process involving oxidation, dehydration and reduction
Gene Name:
rfbB
Uniprot ID:
P37759
Molecular weight:
40558
Reactions
dTDP-glucose = dTDP-4-dehydro-6-deoxy-D-glucose + H(2)O.
General function:
Involved in glucose-1-phosphate thymidylyltransferase activity
Specific function:
Catalyzes the formation of dTDP-glucose, from dTTP and glucose 1-phosphate, as well as its pyrophosphorolysis
Gene Name:
rmlA2
Uniprot ID:
P61887
Molecular weight:
32734
Reactions
dTTP + alpha-D-glucose 1-phosphate = diphosphate + dTDP-glucose.