ECMDB: 2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate (ECMDB20039) (M2MDB000888)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)XML

Proteins (1013)

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

MOL SDF PDB SMILES InChI

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

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 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	53.15 m³·mol⁻¹	ChemAxon
Polarizability	22.37 Å³	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:

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

Protein Details

1. Phospho-2-dehydro-3-deoxyheptonate aldolase, Trp-sensitive

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.

Protein Details

2. Phospho-2-dehydro-3-deoxyheptonate aldolase, Tyr-sensitive

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.

Protein Details

3. 3-dehydroquinate synthase

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.

Protein Details

4. Phospho-2-dehydro-3-deoxyheptonate aldolase, Phe-sensitive

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.

2-Dehydro-3-deoxy-D-arabino-heptonate 7-phosphate (ECMDB20039) (M2MDB000888)

Structure for #<Compound:0xaa39df14>

Enzymes

Reactions

Reactions

Reactions

Reactions