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Identification
YMDB IDYMDB00031
Name7-phospho-2-dehydro-3-deoxy-D-arabino-heptonic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description7-phospho-2-dehydro-3-deoxy-D-arabino-heptonic acid, also known as 2-dahp or 3-deoxy-arabino-heptulonate 7-phosphate, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Based on a literature review very few articles have been published on 7-phospho-2-dehydro-3-deoxy-D-arabino-heptonic acid.
Structure
Thumb
Synonyms
  • 2-Dahp
  • 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate
  • 2-dehydro-3-Deoxy-D-arabino-heptonic acid 7-phosphoric acid
  • 2-dehydro-3-Deoxy-D-arabino-heptulosonic acid-7-phosphate
  • 3-Deoxy-arabino-heptulonate 7-phosphate
  • 3-Deoxy-arabino-heptulonic acid 7-phosphoric acid
  • 3-Deoxy-D-arabino-2-heptulosonate 7-(dihydrogen phosphate)
  • 3-Deoxy-D-arabino-2-heptulosonic acid
  • 3-deoxy-D-arabino-2-heptulosonic acid 7-(dihydrogen phosphate)
  • 3-Deoxy-D-arabino-2-heptulosonic acid 7-(dihydrogen phosphoric acid)
  • 3-Deoxy-D-arabino-hept-2-ulosonate 7-phosphate
  • 3-Deoxy-D-arabino-hept-2-ulosonic acid 7-phosphoric acid
  • 3-Deoxy-D-arabino-heptulosonate 7-phosphate
  • 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-phosphoric acid
  • 3-Deoxyarabinoheptulosonate-7-phosphate
  • 7-phospho-2-keto-3-Deoxy-D-arabinoheptonate
  • DAHP
  • 7-Phospho-2-dehydro-3-deoxy-D-arabino-heptonate
CAS number2627-73-8
WeightAverage: 288.1459
Monoisotopic: 288.024633148
InChI KeyPJWIPEXIFFQAQZ-PUFIMZNGSA-N
InChIInChI=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
IUPAC Name(4R,5S,6R)-4,5,6-trihydroxy-2-oxo-7-(phosphonooxy)heptanoic acid
Traditional IUPAC NameDAHP
Chemical FormulaC7H13O10P
SMILESO[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
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
  • mitochondrion
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Phenylalanine, tyrosine and tryptophan biosynthesisec00400 Map00400
SMPDB ReactionsNot Available
KEGG Reactions
D-Erythrose 4-phosphate + Phosphoenolpyruvic acid + waterphosphate + 7-phospho-2-dehydro-3-deoxy-D-arabino-heptonic acid
7-phospho-2-dehydro-3-deoxy-D-arabino-heptonic acid3-Dehydroquinate + phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006w-6920000000-01ac7cd5df7cb6d11ab7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00du-1490000000-b500894b2362a345803fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-5930000000-a9d3893a2dec466630eeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00xr-9700000000-3199033968d25ee1d235JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002k-6940000000-98d2442ffe3031d309f1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9200000000-37861b420da4e96055acJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-0ba308fea596aa1da1c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-007c-1590000000-5032f9123dae327ae7fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fr2-9700000000-7ee2c3c29df5d7c3c466JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9100000000-5648242eb0703edfc1a4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-2090000000-303f8ce9daad2d0d8370JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9300000000-b3e39bf1c93cf778ae7cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9000000000-5c6f9eb036b780095d5aJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Konig, V., Pfeil, A., Braus, G. H., Schneider, T. R. (2004). "Substrate and metal complexes of 3-deoxy-D-arabino-heptulosonate-7-phosphate synthase from Saccharomyces cerevisiae provide new insights into the catalytic mechanism." J Mol Biol 337:675-690.15019786
  • Larimer, F. W., Morse, C. C., Beck, A. K., Cole, K. W., Gaertner, F. H. (1983). "Isolation of the ARO1 cluster gene of Saccharomyces cerevisiae." Mol Cell Biol 3:1609-1614.6355828
  • Teshiba, S., Furter, R., Niederberger, P., Braus, G., Paravicini, G., Hutter, R. (1986). "Cloning of the ARO3 gene of Saccharomyces cerevisiae and its regulation." Mol Gen Genet 205:353-357.2880280
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18150
HMDB IDHMDB0304124
Pubchem Compound ID160647
Kegg IDC04691
ChemSpider ID24785546
FOODB IDFDB030419
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in 3-dehydroquinate dehydratase activity
Specific function:
The AROM polypeptide catalyzes 5 consecutive enzymatic reactions in prechorismate polyaromatic amino acid biosynthesis
Gene Name:
ARO1
Uniprot ID:
P08566
Molecular weight:
174754.0
Reactions
3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate → 3-dehydroquinate + phosphate.
3-dehydroquinate → 3-dehydroshikimate + H(2)O.
Shikimate + NADP(+) → 3-dehydroshikimate + NADPH.
ATP + shikimate → ADP + shikimate 3-phosphate.
Phosphoenolpyruvate + 3-phosphoshikimate → phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate.
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:
ARO4
Uniprot ID:
P32449
Molecular weight:
39748.80078
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:
ARO3
Uniprot ID:
P14843
Molecular weight:
41069.5
Reactions
Phosphoenolpyruvate + D-erythrose 4-phosphate + H(2)O → 3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate + phosphate.