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Record Information
Version	2.0
Creation Date	2012-05-31 13:49:58 -0600
Update Date	2015-09-13 15:15:22 -0600
Secondary Accession Numbers	ECMDB01328
Identification
Name:	dTDP-D-Glucose
Description	dTDP-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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa9de2c50> Close
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.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Pyrimidine nucleotides
Sub Class	Pyrimidine nucleotide sugars
Direct Parent	Pyrimidine nucleotide sugars
Alternative Parents	Pyrimidine 2'-deoxyribonucleoside diphosphates Pentose phosphates Monosaccharide phosphates Organic pyrophosphates Monoalkyl phosphates Pyrimidones Oxanes Hydropyrimidines Tetrahydrofurans Vinylogous amides Heteroaromatic compounds Ureas Lactams Secondary alcohols Polyols Oxacyclic compounds Azacyclic compounds Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
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 Framework	Aromatic heteromonocyclic compounds
External Descriptors	dTDP-alpha-D-glucose (CHEBI:35248 )
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source LogP: -5.568 PhysProp
Predicted Properties	Property Value Source Water Solubility 11.2 g/L ALOGPS logP -1.2 ALOGPS logP -3.7 ChemAxon logS -1.7 ALOGPS pKa (Strongest Acidic) 1.73 ChemAxon pKa (Strongest Basic) -3 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 13 ChemAxon Hydrogen Donor Count 8 ChemAxon Polar Surface Area 271.31 Ų ChemAxon Rotatable Bond Count 9 ChemAxon Refractivity 109.3 m³·mol⁻¹ ChemAxon Polarizability 46.61 ų ChemAxon Number of Rings 3 ChemAxon Bioavailability 0 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	Thymidine 5'-triphosphate + Glucose 1-phosphate + Hydrogen ion <> dTDP-D-Glucose + Pyrophosphate dTDP-D-Glucose <> 4,6-Dideoxy-4-oxo-dTDP-D-glucose + Water Thymidine 5'-triphosphate + Glucose 1-phosphate <> Pyrophosphate + dTDP-D-Glucose dTDP-D-Glucose <> dTDP-D-Galactose dTDP-D-Glucose > dTDP-4-dehydro-6-deoxy-D-glucose + Water Thymidine 5'-triphosphate + Hydrogen ion + Glucose 1-phosphate > Pyrophosphate + dTDP-D-Glucose Alpha-D-glucose 1-phosphate + Thymidine 5'-triphosphate + Hydrogen ion > Pyrophosphate + dTDP-D-Glucose dTDP-D-Glucose > Water + 4,6-Dideoxy-4-oxo-dTDP-D-glucose α-D-glucose 1-phosphate + Thymidine 5'-triphosphate + Hydrogen ion > dTDP-D-Glucose + Pyrophosphate dTDP-D-Glucose <> dTDP-D-Galactose dTDP-D-Glucose <>4 4,6-Dideoxy-4-oxo-dTDP-D-glucose + Water Thymidine 5'-triphosphate + Glucose 1-phosphate + Hydrogen ion <> dTDP-D-Glucose + Pyrophosphate
SMPDB Pathways:	O-antigen building blocks biosynthesis PW002089 Secondary Metabolites: enterobacterial common antigen biosynthesis PW000959 Secondary Metabolites: enterobacterial common antigen biosynthesis 2 PW002045 Starch and sucrose metabolism PW000941
KEGG Pathways:	Biosynthesis of vancomycin group antibiotics ec01055 Metabolic pathways eco01100 Polyketide sugar unit biosynthesis ec00523 Starch and sucrose metabolism ec00500 Streptomycin biosynthesis ec00521
EcoCyc Pathways:	dTDP-L-rhamnose biosynthesis I DTDPRHAMSYN-PWY enterobacterial common antigen biosynthesis ECASYN-PWY
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-054p-7920560000-231b6626719eee6c053e View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive splash10-0600-9411517000-1aaf284fc97b157c78d4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004i-0900000000-312a08522e3cb22b111b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-004i-2921000000-d3da9a944bb5a8c62cfb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-004i-4900000000-415f5eced8f6fd67d535 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0ik9-1403290000-6b2a8c7a42ac2eaa39c3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0fbc-4905010000-8e6b9db92566b846a800 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a6u-4901000000-4c65036f67c107c3bdf5 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View 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
Links
External Links:	Resource Link CHEBI ID 15700 HMDB ID HMDB01328 Pubchem Compound ID 439324 Kegg ID C00842 ChemSpider ID 388455 Wikipedia ID Not Available BioCyc ID DTDP-D-GLUCOSE EcoCyc ID DTDP-D-GLUCOSE

Enzymes