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
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 IDNot Available
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.