Record Information
Version2.0
Creation Date2012-05-31 14:24:15 -0600
Update Date2015-06-03 17:19:10 -0600
Secondary Accession Numbers
  • ECMDB20039
Identification
Name:2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate
Description2-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
Thumb
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide phosphates
Alternative Parents
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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility14.1 g/LALOGPS
logP-2.5ALOGPS
logP-2.5ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)1.47ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area181.82 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity53.15 m³·mol⁻¹ChemAxon
Polarizability22.37 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Metabolic pathways eco01100
  • Phenylalanine, tyrosine and tryptophan biosynthesis ec00400
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006w-6920000000-01ac7cd5df7cb6d11ab7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00du-1490000000-b500894b2362a345803fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-5930000000-a9d3893a2dec466630eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-9700000000-3199033968d25ee1d235View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002k-6940000000-98d2442ffe3031d309f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-37861b420da4e96055acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-0ba308fea596aa1da1c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-007c-1590000000-5032f9123dae327ae7fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fr2-9700000000-7ee2c3c29df5d7c3c466View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9100000000-5648242eb0703edfc1a4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-2090000000-303f8ce9daad2d0d8370View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9300000000-b3e39bf1c93cf778ae7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9000000000-5c6f9eb036b780095d5aView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView 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
External Links:
ResourceLink
CHEBI ID18150
HMDB IDHMDB0304124
Pubchem Compound ID160647
Kegg IDC04691
ChemSpider ID80
Wikipedia IDNot Available
BioCyc ID3-DEOXY-D-ARABINO-HEPTULOSONATE-7-P
EcoCyc ID3-DEOXY-D-ARABINO-HEPTULOSONATE-7-P

Enzymes

General function:
Involved in catalytic activity
Specific function:
Stereospecific condensation of phosphoenolpyruvate (PEP) and D-erythrose-4-phosphate (E4P) giving rise to 3-deoxy-D- arabino-heptulosonate-7-phosphate (DAHP)
Gene Name:
aroH
Uniprot ID:
P00887
Molecular weight:
38735
Reactions
Phosphoenolpyruvate + D-erythrose 4-phosphate + H(2)O = 3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate + phosphate.
General function:
Involved in catalytic activity
Specific function:
Stereospecific condensation of phosphoenolpyruvate (PEP) and D-erythrose-4-phosphate (E4P) giving rise to 3-deoxy-D- arabino-heptulosonate-7-phosphate (DAHP)
Gene Name:
aroF
Uniprot ID:
P00888
Molecular weight:
38804
Reactions
Phosphoenolpyruvate + D-erythrose 4-phosphate + H(2)O = 3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate + phosphate.
General function:
Involved in 3-dehydroquinate synthase activity
Specific function:
3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate = 3-dehydroquinate + phosphate
Gene Name:
aroB
Uniprot ID:
P07639
Molecular weight:
38881
Reactions
3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate = 3-dehydroquinate + phosphate.
General function:
Involved in catalytic activity
Specific function:
Stereospecific condensation of phosphoenolpyruvate (PEP) and D-erythrose-4-phosphate (E4P) giving rise to 3-deoxy-D- arabino-heptulosonate-7-phosphate (DAHP)
Gene Name:
aroG
Uniprot ID:
P0AB91
Molecular weight:
38009
Reactions
Phosphoenolpyruvate + D-erythrose 4-phosphate + H(2)O = 3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate + phosphate.