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Record Information
Version	2.0
Creation Date	2012-05-31 13:51:28 -0600
Update Date	2015-09-17 15:41:11 -0600
Secondary Accession Numbers	ECMDB01391
Identification
Name:	GDP-4-Dehydro-6-L-deoxygalactose
Description	GDP-4-dehydro-6-L-deoxygalactose is a member of the chemical class known as Purine Nucleotide Sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. GDP-6-deoxy-D-talose biosynthetic pathway involve the enzyme GDP-4-keto-6-deoxy-D-mannose-3-dehydratase, which catalyzes the third step in colitose production, which is the removal of the hydroxyl group at C3' of GDP-4-keto-6-deoxymannose. (PMID 16943443)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xac41e1d0> Close
Synonyms:	GDP-4-Dehydro-6-deoxy-D-talose GDP-4-Dehydro-6-L-deoxygalactose GDP-4-Keto-6-deoxy-D-mannose GDP-4-Keto-6-deoxymannose GDP-4-Keto-6-L-deoxygalactose GDP-4-Oxo-6-deoxy-D-mannose GDP-4-Oxo-6-deoxymannose GDP-DDMan
Chemical Formula:	C16H23N5O15P2
Weight:	Average: 587.3258 Monoisotopic: 587.066588115
InChI Key:	PNHLMHWWFOPQLK-GTXIGXBOSA-N
InChI:	InChI=1S/C16H23N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,8-11,14-15,23-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5?,8+,9+,10+,11-,14+,15?/m0/s1
CAS number:	Not Available
IUPAC Name:	[({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][(3,4-dihydroxy-6-methyl-5-oxooxan-2-yl)oxy]phosphinic acid
Traditional IUPAC Name:	{[3,4-dihydroxy-5-(6-hydroxy-2-imino-3H-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(3,4-dihydroxy-6-methyl-5-oxooxan-2-yl)oxyphosphinic acid
SMILES:	C[C@@H]1OC(OP(O)(=O)OP(O)(=O)OCC2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=C(N)NC3=O)[C@@H](O)[C@H](O)C1=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.
Kingdom	Organic compounds
Super Class	Nucleosides, nucleotides, and analogues
Class	Purine nucleotides
Sub Class	Purine ribonucleotides
Direct Parent	Purine ribonucleoside diphosphates
Alternative Parents	Purine ribonucleoside monophosphates Pentose phosphates Beta amino acids and derivatives Glycosylamines 6-aminopurines Monosaccharide phosphates Organic pyrophosphates Aminopyrimidines and derivatives Monoalkyl phosphates N-substituted imidazoles N-acyl amines Imidolactams Tetrahydrofurans Heteroaromatic compounds Secondary carboxylic acid amides Secondary alcohols Alkylthiols Azacyclic compounds Oxacyclic compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Primary amines Organopnictogen compounds
Substituents	Purine ribonucleoside diphosphate Purine ribonucleoside monophosphate Pentose phosphate Pentose-5-phosphate Beta amino acid or derivatives Glycosyl compound N-glycosyl compound 6-aminopurine Pentose monosaccharide Monosaccharide phosphate Organic pyrophosphate Imidazopyrimidine Purine Aminopyrimidine Monoalkyl phosphate N-acyl-amine N-substituted imidazole Organic phosphoric acid derivative Pyrimidine Fatty amide Imidolactam Monosaccharide Fatty acyl Phosphoric acid ester Alkyl phosphate Azole Heteroaromatic compound Imidazole Tetrahydrofuran Secondary alcohol Secondary carboxylic acid amide Amino acid or derivatives Carboxamide group Organoheterocyclic compound Carboxylic acid derivative Alkylthiol Oxacycle Azacycle Organic oxide Organooxygen compound Organosulfur compound Carbonyl group Organopnictogen compound Organic nitrogen compound Organic oxygen compound Hydrocarbon derivative Alcohol Organonitrogen compound Primary amine Amine Aromatic heteropolycyclic compound
Molecular Framework	Aromatic heteropolycyclic 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 6.35 g/L ALOGPS logP -1.3 ALOGPS logP -3.6 ChemAxon logS -2 ALOGPS pKa (Strongest Acidic) 1.74 ChemAxon pKa (Strongest Basic) 4.94 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 16 ChemAxon Hydrogen Donor Count 9 ChemAxon Polar Surface Area 305.03 Ų ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 126.78 m³·mol⁻¹ ChemAxon Polarizability 49.89 ų ChemAxon Number of Rings 4 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:	Guanosine diphosphate mannose > GDP-4-Dehydro-6-L-deoxygalactose + GDP-4-Dehydro-6-L-deoxygalactose
SMPDB Pathways:	Amino sugar and nucleotide sugar metabolism II PW000887
KEGG Pathways:	Amino sugar and nucleotide sugar metabolism ec00520 Fructose and mannose metabolism ec00051
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 splash10-0udi-0910420000-760094d9b1806f9b8e38 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0udi-0910000000-de61a709d7ef35f70c07 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0udi-1900000000-db427638344d393a59bf View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0f79-3901480000-aade95882a4e80aeb76e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0udi-1901000000-d4665d08dec79b007630 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-0pdl-3900000000-0a1076532e579915ae32 View in MoNA
References
References:	Cook, P. D., Thoden, J. B., Holden, H. M. (2006). "The structure of GDP-4-keto-6-deoxy-D-mannose-3-dehydratase: a unique coenzyme B6-dependent enzyme." Protein Sci 15:2093-2106. Pubmed: 16943443 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
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 16955 HMDB ID HMDB01391 Pubchem Compound ID 731 Kegg ID C01222 ChemSpider ID 711 Wikipedia ID Not Available BioCyc ID GDP-4-DEHYDRO-6-L-DEOXYGALACTOSE EcoCyc ID GDP-4-DEHYDRO-6-L-DEOXYGALACTOSE

Enzymes