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Record Information
Version	2.0
Creation Date	2012-05-31 14:02:47 -0600
Update Date	2015-06-03 15:54:38 -0600
Secondary Accession Numbers	ECMDB04033
Identification
Name:	CDPglucose
Description	CDPglucose 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. GDP-D-glucose is involved in Ebosin biosynthesis. The CDP-D glucose synthase encoded by ste17 gene is involved in the formation of nucleotide sugar (CDP-D-glucose) as glucose precursor in Ebosin biosynthesis. (PMID 19330326)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xa964c2fc> Close
Synonyms:	CDP-D-Glucose CDP-GLC CDP-Glucose
Chemical Formula:	C15H23N3O16P2
Weight:	Average: 563.3011 Monoisotopic: 563.055354727
InChI Key:	CGPHZDRCVSLMCF-JZMIEXBBSA-L
InChI:	InChI=1S/C15H25N3O16P2/c16-7-1-2-18(15(25)17-7)13-11(23)9(21)6(31-13)4-30-35(26,27)34-36(28,29)33-14-12(24)10(22)8(20)5(3-19)32-14/h1-2,5-6,8-14,19-24H,3-4H2,(H,26,27)(H,28,29)(H2,16,17,25)/p-2/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1
CAS number:	Not Available
IUPAC Name:	1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-({[hydroxy({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl phosphonato]oxy}methyl)oxolan-2-yl]-4-imino-1,4-dihydropyrimidin-2-olate
Traditional IUPAC Name:	1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[({hydroxy[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphoryl phosphonato}oxy)methyl]oxolan-2-yl]-4-iminopyrimidin-2-olate
SMILES:	[H][C@]1(COP([O-])(=O)OP(O)(=O)O[C@@]2([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]2([H])O)O[C@@]([H])(N2C=CC(=N)N=C2[O-])[C@]([H])(O)[C@]1([H])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 ribonucleoside diphosphates Pentose phosphates Glycosylamines Organic pyrophosphates Monosaccharide phosphates Pyrimidones Aminopyrimidines and derivatives Oxanes Imidolactams Hydropyrimidines Alkyl phosphates Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Polyols Oxacyclic compounds Azacyclic compounds Primary amines Primary alcohols Organopnictogen compounds Organic oxides Hydrocarbon derivatives Organic anions
Substituents	Pyrimidine nucleotide sugar Pyrimidine ribonucleoside diphosphate Pentose-5-phosphate Pentose phosphate N-glycosyl compound Glycosyl compound Organic pyrophosphate Monosaccharide phosphate Pyrimidone Aminopyrimidine Imidolactam Alkyl phosphate Pyrimidine Phosphoric acid ester Oxane Organic phosphoric acid derivative Monosaccharide Hydropyrimidine Heteroaromatic compound Tetrahydrofuran Secondary alcohol Oxacycle Azacycle Organoheterocyclic compound Polyol Organic nitrogen compound Organic oxygen compound Organopnictogen compound Organic oxide Hydrocarbon derivative Primary amine Primary alcohol Organooxygen compound Organonitrogen compound Amine Alcohol Organic anion Aromatic heteromonocyclic compound
Molecular Framework	Aromatic heteromonocyclic compounds
External Descriptors	Not Available
Physical Properties
State:	Not Available
Charge:	-2
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 31.6 g/L ALOGPS logP -1.8 ALOGPS logP -6 ChemAxon logS -1.3 ALOGPS pKa (Strongest Acidic) 1.67 ChemAxon pKa (Strongest Basic) 3.26 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 16 ChemAxon Hydrogen Donor Count 8 ChemAxon Polar Surface Area 307.47 Ų ChemAxon Rotatable Bond Count 9 ChemAxon Refractivity 129.28 m³·mol⁻¹ ChemAxon Polarizability 46.15 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:
SMPDB Pathways:	Starch and sucrose metabolism PW000941
KEGG Pathways:	Amino sugar and nucleotide sugar metabolism ec00520 Starch and sucrose metabolism ec00500
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 splash10-03di-1400090000-9e3f1417fd829a7180e9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-06r6-1270090000-dcb8a11f162b4ae61daf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0btd-9610000000-6272a9f451219c152b68 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-03di-1200090000-031c11d5489f5b49db75 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-03fu-9815070000-0babbcff6d2444fdade8 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0560-9200000000-16e81128d19377fb9426 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:	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 Qi, X. Q., Sun, Q. L., Bai, L. P., Shan, J. J., Zhang, Y., Zhang, R., Li, Y. (2009). "Identification of alpha-D-glucose-1-phosphate cytidylyltransferase involved in Ebosin biosynthesis of Streptomyces sp. 139." Appl Microbiol Biotechnol 83:361-368. Pubmed: 19330326 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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 137927 HMDB ID HMDB03369 Pubchem Compound ID 25245528 Kegg ID C00501 ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID CDP-D-GLUCOSE EcoCyc ID CDP-D-GLUCOSE