P. aeruginosa Metabolome Database: 5-O-(1-Carboxyvinyl)-3-phosphoshikimate (PAMDB000954)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000954

Identification

Name:

5-O-(1-Carboxyvinyl)-3-phosphoshikimate

Description:

5-o-(1-carboxyvinyl)-3-phosphoshikimate is a member of the chemical class known as Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group. The shikimate pathway enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS) is the target of the broad spectrum herbicide glyphosate. (PMID 19211556) 5-Enolpyruvylshikimate-3-phosphate (EPSP) synthase (AroA) is a key enzyme in the aromatic amino acid biosynthetic pathway in microorganisms and plants, and is the target of the herbicide glyphosate. (PMID 16469313)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

3-Enolpyruvyl-shikimate-5-P
3-Enolpyruvyl-shikimate-5-phosphate
3-Enolpyruvyl-shikimic acid-5-P
3-Enolpyruvyl-shikimic acid-5-phosphoric acid
5-ENOLPYRUVYLSHIKIMATE-3-PHOSPHATE
5-ENOLPYRUVYLSHIKIMic acid-3-phosphoric acid
5-O-(1-Carboxyvinyl)-3-phosphoshikimate
5-O-(1-Carboxyvinyl)-3-phosphoshikimic acid
5EPS3P
EPS
EPSP
O5-(1-carboxyvinyl)-3-phosphate shikimate
O5-(1-Carboxyvinyl)-3-phosphoric acid shikimic acid
O5-(1-carboxyvinyl)-3-phosphoshikimate
O5-(1-carboxyvinyl)-3-phosphoshikimic acid

Chemical Formula:

C₁₀H₁₃O₁₀P

Average Molecular Weight:

324.178

Monoisotopic Molecular Weight:

324.024633148

InChI Key:

QUTYKIXIUDQOLK-PRJMDXOYSA-N

InChI:

InChI=1S/C10H13O10P/c1-4(9(12)13)19-6-2-5(10(14)15)3-7(8(6)11)20-21(16,17)18/h3,6-8,11H,1-2H2,(H,12,13)(H,14,15)(H2,16,17,18)/t6-,7-,8+/m1/s1

CAS number:

89771-75-5

IUPAC Name:

(3R,4S,5R)-5-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid

Traditional IUPAC Name:

(3R,4S,5R)-5-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid

SMILES:

O[C@H]1[C@@H](CC(=C[C@H]1OP(O)(O)=O)C(O)=O)OC(=C)C(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.

Kingdom

Organic compounds

Super Class

Organophosphorus compounds

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Monoalkyl phosphates

Alternative Parents

Substituents

Monoalkyl phosphate
Organic phosphate
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

dicarboxylic acid (CHEBI:16257 )
phosphoshikimic acid (CHEBI:16257 )

Physical Properties

State:

Not Available

Charge:

-4

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	5.63 mg/mL	ALOGPS
logP	-0.83	ALOGPS
logP	-1.1	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.31	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.82 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	65.58 m³·mol^-1	ChemAxon
Polarizability	26.13 Å³	ChemAxon
Number of Rings	1	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:

5-O-(1-Carboxyvinyl)-3-phosphoshikimate <> Chorismate + Phosphate
Shikimate 3-phosphate + Phosphoenolpyruvic acid <> 5-O-(1-Carboxyvinyl)-3-phosphoshikimate + Phosphate
Phosphoenolpyruvic acid + Shikimate 3-phosphate > Inorganic phosphate + 5-O-(1-Carboxyvinyl)-3-phosphoshikimate
5-O-(1-Carboxyvinyl)-3-phosphoshikimate > Chorismate + Inorganic phosphate

Pathways:

Metabolic pathways pae01100
Phenylalanine, tyrosine and tryptophan biosynthesis pae00400

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6r-3079000000-4fc890f00ff2a2c1037e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-2092000000-1d9cc5b2cadb3db98046	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ac1-8930000000-4ff9712d95c3009d70c3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00fr-6059000000-24817ec47586471218ad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9051000000-6520d5fbd79bb20ba04a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-07abacf74b9ddf9a73c8	View in MoNA

References

References:

Funke, T., Yang, Y., Han, H., Healy-Fried, M., Olesen, S., Becker, A., Schonbrunn, E. (2009). "Structural basis of glyphosate resistance resulting from the double mutation Thr97 -> Ile and Pro101 -> Ser in 5-enolpyruvylshikimate-3-phosphate synthase from Escherichia coli." J Biol Chem 284:9854-9860. Pubmed: 19211556
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
Sun, Y. C., Li, Y., Zhang, H., Yan, H. Q., Dowling, D. N., Wang, Y. P. (2006). "Reconstitution of the enzyme AroA and its glyphosate tolerance by fragment complementation." FEBS Lett 580:1521-1527. Pubmed: 16469313
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	16257
HMDB ID	Not Available
Pubchem Compound ID	439463
Kegg ID	C01269
ChemSpider ID	388567
Wikipedia ID	Not Available
BioCyc ID	3-ENOLPYRUVYL-SHIKIMATE-5P
EcoCyc ID	3-ENOLPYRUVYL-SHIKIMATE-5P
Ligand Expo	EPS

5-O-(1-Carboxyvinyl)-3-phosphoshikimate (PAMDB000954)

Structure for 5-O-(1-Carboxyvinyl)-3-phosphoshikimate (PAMDB000954)