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Record Information
Version	2.0
Creation Date	2015-09-08 17:49:56 -0600
Update Date	2015-09-14 16:46:07 -0600
Secondary Accession Numbers	ECMDB24182
Identification
Name:	3-deoxy-D-arabino-heptulosonate-7-phosphate
Description	3-Deoxy-D-arabino-heptulosonate-7-phosphate is a member of the chemical class known as Medium-chain Keto Acids and Derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. DAHPS is involved in the biosynthesis of aromatic amino acids. Maritima DAHP synthase is a metalloenzyme. This report is the first description of a thermophilic eubacterial DAHP synthase. (PMID 12743122) DAHPS(Phe) is a metal-catalyzed oxidation system wherein bound substrate protects active-site residues from oxidative attack catalyzed by bound redox metal cofactor. (PMID 10049398) The first regulatory step in the synthesis of aromatic amino acids is catalyzed by 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase (DAHPS). (PMID 15378531) While several similarities exist between the two enzymatic reactions, classic studies on the Escherichia coli enzymes have established that DAHPS is a metalloenzyme, whereas KDO8PS has no metal requirement. aeolicus KDO8PS is a metalloenzyme in vivo and point to a previously unrecognized relationship between the KDO8PS and DAHPS families. (PMID 10811802)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x8db1e0f8> Close
Synonyms:	3-Deoxy-D-arabino-heptulosonic acid-7-phosphoric acid
Chemical Formula:	C7H10O10P
Weight:	Average: 285.122 Monoisotopic: 285.00280426
InChI Key:	PJWIPEXIFFQAQZ-PUFIMZNGSA-K
InChI:	InChI=1S/C7H13O10P/c8-3(1-4(9)7(12)13)6(11)5(10)2-17-18(14,15)16/h3,5-6,8,10-11H,1-2H2,(H,12,13)(H2,14,15,16)/p-3/t3-,5-,6+/m1/s1
CAS number:	Not Available
IUPAC Name:	(4R,5S,6R)-4,5,6-trihydroxy-2-oxo-7-(phosphonatooxy)heptanoate
Traditional IUPAC Name:	(4R,5S,6R)-4,5,6-trihydroxy-2-oxo-7-(phosphonatooxy)heptanoate
SMILES:	[H][C@@](O)(COP([O-])([O-])=O)[C@@]([H])(O)[C@]([H])(O)CC(=O)C([O-])=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
Kingdom	Organic compounds
Super Class	Organic oxygen compounds
Class	Organooxygen compounds
Sub Class	Carbohydrates and carbohydrate conjugates
Direct Parent	Monosaccharide phosphates
Alternative Parents	Heptoses Medium-chain keto acids and derivatives Sugar acids and derivatives Beta-hydroxy ketones Alpha-keto acids and derivatives Alkyl phosphates Secondary alcohols Polyols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Organic anions
Substituents	Heptose monosaccharide Monosaccharide phosphate Medium-chain keto acid Sugar acid Alpha-keto acid Beta-hydroxy ketone Alkyl phosphate Keto acid Phosphoric acid ester Organic phosphoric acid derivative Secondary alcohol Ketone Carboxylic acid derivative Carboxylic acid Polyol Monocarboxylic acid or derivatives Alcohol Carbonyl group Organic oxide Hydrocarbon derivative Organic anion Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	carbohydrate acid derivative anion (CHEBI:58394 ) monocarboxylic acid anion (CHEBI:58394 ) organophosphate oxoanion (CHEBI:58394 )
Physical Properties
State:	Not Available
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 51.1 g/L ALOGPS logP -1.6 ALOGPS logP -2.5 ChemAxon logS -0.82 ALOGPS pKa (Strongest Acidic) 1.47 ChemAxon pKa (Strongest Basic) -3.3 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 9 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 190.31 Ų ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 61.75 m³·mol⁻¹ ChemAxon Polarizability 21.76 ų ChemAxon Number of Rings 0 ChemAxon Bioavailability 1 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:	D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid > Phosphate + 3-deoxy-D-arabino-heptulosonate-7-phosphate 3-deoxy-D-arabino-heptulosonate-7-phosphate > Phosphate + 3-Dehydroquinate
SMPDB Pathways:	Chorismate biosynthesis PW000816 Secondary Metabolites: Shikimate Pathway PW000985
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 splash10-000i-0090000000-d66aa66ec73357727eaa View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-056r-1190000000-7e7cc8d6f1ccf3f95354 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-056s-8910000000-81bf72773f8d70e9afa1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-001i-1190000000-9a6594a4f74076f0556c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-001i-6390000000-d23ab2618c147f679d11 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-001j-9100000000-19ff6079df0f5e0b8b80 View in MoNA
References
References:	Not Available
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 58394 HMDB ID Not Available Pubchem Compound ID 5460215 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID 3-Deoxy-D-arabino-heptulosonic acid 7-phosphate BioCyc ID Not Available

Enzymes