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Record Information
Version	2.0
Creation Date	2015-09-08 17:50:28 -0600
Update Date	2015-09-14 16:46:47 -0600
Secondary Accession Numbers	ECMDB24258
Identification
Name:	dTDP-thomosamine
Description	dTDP-thomosamine is an intermediate in dTDP-N-acetylthomosamine biosynthesis in E.coli. It is a substrate for the enzyme dTDP-fucosamine acetyltransferase which catalyzes the reaction dTDP-thomosamine + acetyl-CoA -> dTDP-N-acetylthomosamine + coenzyme A + H+. It is also a product for enzyme dTDP-4-dehydro-6-deoxy-D-glucose transaminase which catalyzes reaction dTDP-4-dehydro-6-deoxy-α-D-glucopyranose + L-glutamate -> dTDP-thomosamine + 2-oxoglutarate (BioCyc compound: TDP-D-FUCOSAMINE).
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xae7c4170> Close
Synonyms:	Value Source dTDP-4-Amino-4,6-dideoxy-alpha-D-galactose ChEBI dTDP-alpha-D-Fucosamine ChEBI dTDP-4-Amino-4,6-dideoxy-a-D-galactose Generator dTDP-4-Amino-4,6-dideoxy-α-D-galactose Generator dTDP-a-D-Fucosamine Generator dTDP-Α-D-fucosamine Generator dTDP-4-amino-4,6-Dideoxy-a-D-galactose(1-) Generator dTDP-4-amino-4,6-Dideoxy-α-D-galactose(1-) Generator
Chemical Formula:	C16H26N3O14P2
Weight:	Average: 546.339 Monoisotopic: 546.089550105
InChI Key:	UIVJXHWSIFBBCY-FQLHZTMTSA-M
InChI:	InChI=1S/C16H27N3O14P2/c1-6-4-19(16(24)18-14(6)23)10-3-8(20)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)12(21)11(17)7(2)30-15/h4,7-13,15,20-22H,3,5,17H2,1-2H3,(H,25,26)(H,27,28)(H,18,23,24)/p-1/t7-,8+,9-,10-,11+,12+,13-,15-/m1/s1
CAS number:	Not Available
IUPAC Name:	1-[(2R,4S,5R)-5-[({[({[(2R,3R,4S,5R,6R)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-2-yl]-5-methyl-2-oxo-1,2-dihydropyrimidin-4-olate
Traditional IUPAC Name:	1-[(2R,4S,5R)-5-{[({[(2R,3R,4S,5R,6R)-5-amino-3,4-dihydroxy-6-methyloxan-2-yl]oxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-2-yl]-5-methyl-2-oxopyrimidin-4-olate
SMILES:	[H][C@]1(O)C[C@@]([H])(O[C@]1([H])COP(O)(=O)OP(O)(=O)O[C@@]1([H])O[C@]([H])(C)[C@]([H])(N)[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 polyprenyl phospho carbohydrates. These are polyprenyl phosphates with a carbohydrate moiety attached to it.
Kingdom	Organic compounds
Super Class	Lipids and lipid-like molecules
Class	Prenol lipids
Sub Class	Polyprenols
Direct Parent	Polyprenyl phospho carbohydrates
Alternative Parents	Polyterpenoids Bactoprenol diphosphates Polyprenyl monophosphates N-acyl-alpha-hexosamines Hexoses Isoprenoid phosphates Monosaccharide phosphates Organic pyrophosphates Monoalkyl phosphates Oxanes Acetamides Secondary carboxylic acid amides Secondary alcohols Oxacyclic compounds Organonitrogen compounds Carbonyl compounds Organic oxides Primary alcohols Hydrocarbon derivatives Organopnictogen compounds
Substituents	Polyterpenoid Polyprenyl phospho carbohydrate Bactoprenol diphosphate Polyprenyl monophosphate Polyprenyl phosphate skeleton N-acyl-alpha-hexosamine Hexose monosaccharide Isoprenoid phosphate Monosaccharide phosphate Organic pyrophosphate Monoalkyl phosphate Monosaccharide Organic phosphoric acid derivative Oxane Phosphoric acid ester Alkyl phosphate Acetamide Carboxamide group Secondary carboxylic acid amide Secondary alcohol Oxacycle Carboxylic acid derivative Organoheterocyclic compound Carbonyl group Organic oxide Alcohol Organopnictogen compound Organic oxygen compound Organic nitrogen compound Hydrocarbon derivative Primary alcohol Organonitrogen compound Organooxygen compound Aliphatic heteromonocyclic compound
Molecular Framework	Aliphatic heteromonocyclic compounds
External Descriptors	polyprenyl glycosyl phosphate (CHEBI:16511 ) N-acyl-D-glucosamine 1-phosphate (CHEBI:16511 )
Physical Properties
State:	Not Available
Charge:	-1
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 22.5 g/L ALOGPS logP -1.7 ALOGPS logP -3.6 ChemAxon logS -1.4 ALOGPS pKa (Strongest Acidic) 1.73 ChemAxon pKa (Strongest Basic) 8.89 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 13 ChemAxon Hydrogen Donor Count 6 ChemAxon Polar Surface Area 263.19 Ų ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 120.29 m³·mol⁻¹ ChemAxon Polarizability 45.62 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:	Acetyl-CoA + dTDP-thomosamine > TDP-Fuc4NAc + Coenzyme A + Hydrogen ion L-Glutamic acid + dTDP-4-dehydro-6-deoxy-D-glucose + L-Glutamate > Oxoglutaric acid + dTDP-thomosamine
SMPDB Pathways:	Secondary Metabolites: enterobacterial common antigen biosynthesis PW000959 Secondary Metabolites: enterobacterial common antigen biosynthesis 2 PW002045
KEGG Pathways:	Not Available
EcoCyc Pathways:	Not Available
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0002-1400190000-629ccbef77969751ebb9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0097-0381090000-37ff850190468cd49757 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0a4i-9300000000-47b5012caf79b84af2b6 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-000m-9000040000-4032275cb4d3aee7308f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-052r-9100010000-1233f33c129da68c6986 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-00fr-9100000000-be192b48c764816a4ce5 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:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 68492 HMDB ID Not Available Pubchem Compound ID 70678920 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available

Enzymes