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Record Information
Version	2.0
Creation Date	2012-05-31 14:24:15 -0600
Update Date	2015-06-03 17:19:10 -0600
Secondary Accession Numbers	ECMDB20039
Identification
Name:	2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate
Description	2-dehydro-3-deoxy-D-arabino-heptonate 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:0xad3dfdd0> Close
Synonyms:	2-Dahp 2-dehydro-3-deoxy-D-arabino-heptonate 7-phosphate 2-Dehydro-3-deoxy-D-arabino-heptonic acid 7-phosphate 2-dehydro-3-Deoxy-D-arabino-heptonic acid 7-phosphoric acid 2-Dehydro-3-deoxy-D-arabino-heptulosonate-7-phosphate 2-Dehydro-3-deoxy-D-arabino-heptulosonic acid-7-phosphate 2-dehydro-3-Deoxy-D-arabino-heptulosonic acid-7-phosphoric acid 3-Deoxy-7-O-phosphono-D-arabino-hept-2-ulosonate 3-Deoxy-7-O-phosphono-D-arabino-hept-2-ulosonic acid 3-Deoxy-arabino-heptulonate 7-phosphate 3-Deoxy-arabino-heptulonic acid 7-phosphate 3-Deoxy-arabino-heptulonic acid 7-phosphoric acid 3-Deoxy-arabino-heptulosonate 7-phosphate 3-Deoxy-arabino-heptulosonate-7-P 3-Deoxy-arabino-heptulosonic acid 7-phosphate 3-Deoxy-arabino-heptulosonic acid 7-phosphoric acid 3-Deoxy-arabino-heptulosonic acid-7-P 3-Deoxy-D-arabino-hept-2-ulosonate 7-phosphate 3-Deoxy-D-arabino-hept-2-ulosonate-7-phosphate 3-Deoxy-D-arabino-hept-2-ulosonic acid 7-phosphate 3-Deoxy-D-arabino-hept-2-ulosonic acid 7-phosphoric acid 3-Deoxy-D-arabino-hept-2-ulosonic acid-7-phosphoric acid 3-Deoxy-D-arabino-heptulosonate 7-phosphate 3-Deoxy-D-arabino-heptulosonate-7-P 3-Deoxy-D-arabino-heptulosonate-7-phosphate 3-Deoxy-D-arabino-heptulosonic acid 7-phosphate 3-Deoxy-D-arabino-heptulosonic acid 7-phosphoric acid 3-Deoxy-D-arabino-heptulosonic acid-7-P 3-Deoxy-D-arabino-heptulosonic acid-7-phosphoric acid 3-Deoxyarabinoheptulosonate-7-phosphate 3-Deoxyarabinoheptulosonic acid-7-phosphoric acid 3DAH7P 7-Phospho-2-dehydro-3-deoxy-D-arabino-heptonate 7-Phospho-2-dehydro-3-deoxy-D-arabino-heptonic acid 7-Phospho-2-keto-3-deoxy-D-arabinoheptonate 7-Phospho-2-keto-3-deoxy-D-arabinoheptonic acid DAHP
Chemical Formula:	C7H13O10P
Weight:	Average: 288.1459 Monoisotopic: 288.024633148
InChI Key:	PJWIPEXIFFQAQZ-PUFIMZNGSA-N
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)/t3-,5-,6+/m1/s1
CAS number:	2627-73-8
IUPAC Name:	(4R,5S,6R)-4,5,6-trihydroxy-2-oxo-7-(phosphonooxy)heptanoic acid
Traditional IUPAC Name:	DAHP
SMILES:	O[C@H](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 Monoalkyl phosphates Beta-hydroxy ketones Alpha-keto acids and derivatives Alpha-hydroxy ketones Secondary alcohols Polyols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives
Substituents	Heptose monosaccharide Monosaccharide phosphate Medium-chain keto acid Monoalkyl phosphate Sugar acid Alpha-keto acid Alkyl phosphate Beta-hydroxy ketone Phosphoric acid ester Organic phosphoric acid derivative Keto acid Alpha-hydroxy ketone Secondary alcohol Ketone Polyol Carboxylic acid derivative Carboxylic acid Monocarboxylic acid or derivatives Alcohol Carbonyl group Organic oxide Hydrocarbon derivative Aliphatic acyclic compound
Molecular Framework	Aliphatic acyclic compounds
External Descriptors	ketoaldonic acid phosphate (CHEBI:18150 )
Physical Properties
State:	Not Available
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 14.1 g/L ALOGPS logP -2.5 ALOGPS logP -2.5 ChemAxon logS -1.3 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 6 ChemAxon Polar Surface Area 181.82 Ų ChemAxon Rotatable Bond Count 8 ChemAxon Refractivity 53.15 m³·mol⁻¹ ChemAxon Polarizability 22.37 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 <> 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Phosphate 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate <> 3-Dehydroquinate + Phosphate 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate > Phosphate + 3-Dehydroquinate 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate > 3-Dehydroquinate + Inorganic phosphate Phosphoenolpyruvic acid + D-Erythrose 4-phosphate + Water > 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Inorganic phosphate D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid <>2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Phosphate 2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate <>3 3-Dehydroquinate + Phosphate D-Erythrose 4-phosphate + Water + Phosphoenolpyruvic acid <>2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate + Phosphate 2 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate <>3 3-Dehydroquinate + Phosphate
SMPDB Pathways:	Not Available
KEGG Pathways:	Metabolic pathways eco01100 Phenylalanine, tyrosine and tryptophan biosynthesis ec00400
EcoCyc Pathways:	3-dehydroquinate biosynthesis I PWY-6164
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-006w-6920000000-01ac7cd5df7cb6d11ab7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-00du-1490000000-b500894b2362a345803f View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0006-5930000000-a9d3893a2dec466630ee View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-00xr-9700000000-3199033968d25ee1d235 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-002k-6940000000-98d2442ffe3031d309f1 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9200000000-37861b420da4e96055ac View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-0ba308fea596aa1da1c2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-007c-1590000000-5032f9123dae327ae7fd View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0fr2-9700000000-7ee2c3c29df5d7c3c466 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0002-9100000000-5648242eb0703edfc1a4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00kr-2090000000-303f8ce9daad2d0d8370 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0002-9300000000-b3e39bf1c93cf778ae7c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004j-9000000000-5c6f9eb036b780095d5a 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:	Duewel, H. S., Woodard, R. W. (2000). "A metal bridge between two enzyme families. 3-deoxy-D-manno-octulosonate-8-phosphate synthase from Aquifex aeolicus requires a divalent metal for activity." J Biol Chem 275:22824-22831. Pubmed: 10811802 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 Park, O. K., Bauerle, R. (1999). "Metal-catalyzed oxidation of phenylalanine-sensitive 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase from Escherichia coli: inactivation and destabilization by oxidation of active-site cysteines." J Bacteriol 181:1636-1642. Pubmed: 10049398 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 Wu, J., Howe, D. L., Woodard, R. W. (2003). "Thermotoga maritima 3-deoxy-D-arabino-heptulosonate 7-phosphate (DAHP) synthase: the ancestral eubacterial DAHP synthase?" J Biol Chem 278:27525-27531. Pubmed: 12743122 Xu, J., Hu, C., Shen, S., Wang, W., Jiang, P., Huang, W. (2004). "Requirement of the N-terminus for dimer formation of phenylalanine-sensitive 3-deoxy-D-arabino-heptulosonate synthase AroG of Escherichia coli." J Basic Microbiol 44:400-406. Pubmed: 15378531
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 18150 HMDB ID HMDB0304124 Pubchem Compound ID 160647 Kegg ID C04691 ChemSpider ID 80 Wikipedia ID Not Available BioCyc ID 3-DEOXY-D-ARABINO-HEPTULOSONATE-7-P EcoCyc ID 3-DEOXY-D-ARABINO-HEPTULOSONATE-7-P

Enzymes