You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
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 is an intermediate in phenylalanine, tyrosine and tryptophan biosynthesis pathway. [KEGG]
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
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
DescriptionThis compound belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassMedium-chain keto acids and derivatives
Direct ParentMedium-chain keto acids and derivatives
Alternative Parents
Substituents
  • Medium-chain keto acid
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Saccharide
  • Beta-hydroxy ketone
  • Beta-ketoaldehyde
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Polyol
  • Ketone
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • 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
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 IDNot Available
Pubchem Compound ID160647
Kegg IDC04691
ChemSpider ID24785546
FOODB IDNot Available
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.