Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

Record Information
Version	2.0
Creation Date	2012-07-30 14:55:18 -0600
Update Date	2015-06-03 17:21:10 -0600
Secondary Accession Numbers	ECMDB21327
Identification
Name:	dTDP-4-Dehydro-6-deoxy-L-mannose
Description	4,6-Dideoxy-4-oxo-dTDP-D-glucose is a product of the enzyme TDP-glucose 4,6-dehydratase [EC:4.2.1.46] in the Nucleotide sugars metabolism (KEGG)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x9bc1eddc> Close
Synonyms:	4,6-Dideoxy-4-oxo-dTDP-D-glucose DTDP-4-Dehydro-6-deoxy-D-glucose DTDP-4-Dehydro-6-deoxy-L-mannose DTDP-4-Dehydro-L-rhamnose DTDP-4-Oxo-6-deoxy-D-glucose DTDP-4-Oxo-6-deoxy-L-mannose DTDP-4-Oxo-L-rhamnose DTDP-DDMan TDP-4-Keto-6-deoxy-D-glucose TDP-4-Oxo-6-deoxy-D-glucose Thymidine 5'-[3-(6-deoxy-L-lyxo-hexopyranosyl-4-ulose) dihydrogen diphosphate] Thymidine 5'-[3-(6-deoxy-L-lyxo-hexopyranosyl-4-ulose) dihydrogen diphosphoric acid]
Chemical Formula:	C16H24N2O15P2
Weight:	Average: 546.3137 Monoisotopic: 546.065191132
InChI Key:	PSXWNITXWWECNY-WPTIAVDBSA-N
InChI:	InChI=1S/C16H24N2O15P2/c1-6-4-18(16(24)17-14(6)23)10-3-8(19)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(20)7(2)30-15/h4,7-10,12-13,15,19,21-22H,3,5H2,1-2H3,(H,25,26)(H,27,28)(H,17,23,24)/t7-,8-,9+,10+,12+,13+,15?/m0/s1
CAS number:	Not Available
IUPAC Name:	[({[(3R,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid
Traditional IUPAC Name:	{[(3R,4S,6S)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy(hydroxy)phosphoryl}oxy[(2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxyphosphinic acid
SMILES:	[H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP(O)(=O)OP(O)(=O)OC1([H])O[C@@]([H])(C)C(=O)[C@@]([H])(O)[C@@]1([H])O)N1C=C(C)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 Organic pyrophosphates Pyrimidones Monoalkyl phosphates Hydropyrimidines Oxanes Vinylogous amides Heteroaromatic compounds Tetrahydrofurans Cyclic ketones Ureas Secondary alcohols Lactams Azacyclic compounds Oxacyclic compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds Organonitrogen compounds
Substituents	Pyrimidine nucleotide sugar Pyrimidine 2'-deoxyribonucleoside diphosphate Pentose phosphate Organic pyrophosphate Pyrimidone Monoalkyl phosphate Hydropyrimidine Organic phosphoric acid derivative Pyrimidine Oxane Phosphoric acid ester Alkyl phosphate Heteroaromatic compound Vinylogous amide Tetrahydrofuran Secondary alcohol Lactam Ketone Urea Cyclic ketone Oxacycle Azacycle Organoheterocyclic compound Organooxygen compound Organonitrogen compound Hydrocarbon derivative Organic oxide Organopnictogen compound Organic oxygen compound Organic nitrogen compound Alcohol Carbonyl group Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	dTDP-sugar (CHEBI:15744 )
Physical Properties
State:	Solid
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 16.5 g/L ALOGPS logP -1.1 ALOGPS logP -1.7 ChemAxon logS -1.5 ALOGPS pKa (Strongest Acidic) 1.73 ChemAxon pKa (Strongest Basic) -3.2 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 13 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 251.41 Ų ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 107.31 m³·mol⁻¹ ChemAxon Polarizability 45.3 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:	4,6-Dideoxy-4-oxo-dTDP-D-glucose <> dTDP-4-Dehydro-6-deoxy-L-mannose dTDP-4-Dehydro-6-deoxy-L-mannose + Hydrogen ion + NADPH <> Deoxythymidine diphosphate-L-rhamnose + NADP Deoxythymidine diphosphate-L-rhamnose + NADP <> dTDP-4-Dehydro-6-deoxy-L-mannose + NADPH + Hydrogen ion dTDP-4-dehydro-6-deoxy-D-glucose > dTDP-4-Dehydro-6-deoxy-L-mannose dTDP-6-deoxy-L-mannose + NADP > dTDP-4-Dehydro-6-deoxy-L-mannose + NADPH dTDP-4-Dehydro-6-deoxy-L-mannose + Hydrogen ion + NADPH <> Deoxythymidine diphosphate-L-rhamnose + NADP 4 4,6-Dideoxy-4-oxo-dTDP-D-glucose <> dTDP-4-Dehydro-6-deoxy-L-mannose dTDP-4-Dehydro-6-deoxy-L-mannose + Hydrogen ion + NADPH <> Deoxythymidine diphosphate-L-rhamnose + NADP 4 4,6-Dideoxy-4-oxo-dTDP-D-glucose <> dTDP-4-Dehydro-6-deoxy-L-mannose
SMPDB Pathways:	Not Available
KEGG Pathways:	Metabolic pathways eco01100 Polyketide sugar unit biosynthesis ec00523 Streptomycin biosynthesis ec00521
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (TMS_4_32) - 70eV, Positive Not Available View in JSpectraViewer Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-004i-0900000000-829c0bbe6e6b0eebcc12 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-004i-3911000000-a11100c243372ad6a153 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-004i-4900000000-5969b778751f7221e3eb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0udj-3702390000-eddd4cb79c27055083f3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0fb9-4904010000-927c2bf9bd3ed82c570f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0a6u-5900000000-f47f2109726170ad9d79 View in MoNA MS Mass Spectrum (Electron Ionization) 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 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	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:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 15744 HMDB ID HMDB01399 Pubchem Compound ID 685 Kegg ID C00688 ChemSpider ID 391477 Wikipedia ID Not Available BioCyc ID Not Available

Enzymes