Shikimate-3-Phosphate

Identification

Name
Shikimate-3-Phosphate
Accession Number
DB04328  (EXPT02832)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 254.1312
Monoisotopic: 254.01915384
Chemical Formula
C7H11O8P
InChI Key
QYOJSKGCWNAKGW-PBXRRBTRSA-N
InChI
InChI=1S/C7H11O8P/c8-4-1-3(7(10)11)2-5(6(4)9)15-16(12,13)14/h2,4-6,8-9H,1H2,(H,10,11)(H2,12,13,14)/t4-,5-,6+/m1/s1
IUPAC Name
(3R,4S,5R)-4,5-dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid
SMILES
O[[email protected]@H]1CC(=C[[email protected]@H](OP(O)(O)=O)[[email protected]]1O)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U3-phosphoshikimate 1-carboxyvinyltransferaseNot AvailableEscherichia coli (strain K12)
U3-phosphoshikimate 1-carboxyvinyltransferaseNot AvailableStreptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C03175
PubChem Compound
121947
PubChem Substance
46504914
ChemSpider
108789
BindingDB
100283
ChEBI
17052
ChEMBL
CHEMBL95193
HET
S3P
PDB Entries
1g6s / 1g6t / 1mi4 / 1rf6 / 2gg6 / 2gga / 2ggd / 2iyy / 2iyz / 2o0b
show 14 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility21.0 mg/mLALOGPS
logP-2.1ALOGPS
logP-1.8ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.83 m3·mol-1ChemAxon
Polarizability20.46 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7268
Blood Brain Barrier+0.7203
Caco-2 permeable-0.7061
P-glycoprotein substrateNon-substrate0.601
P-glycoprotein inhibitor INon-inhibitor0.7215
P-glycoprotein inhibitor IINon-inhibitor0.9962
Renal organic cation transporterNon-inhibitor0.9484
CYP450 2C9 substrateNon-substrate0.8686
CYP450 2D6 substrateNon-substrate0.8494
CYP450 3A4 substrateNon-substrate0.5926
CYP450 1A2 substrateNon-inhibitor0.8924
CYP450 2C9 inhibitorNon-inhibitor0.8975
CYP450 2D6 inhibitorNon-inhibitor0.9019
CYP450 2C19 inhibitorNon-inhibitor0.8622
CYP450 3A4 inhibitorNon-inhibitor0.9806
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9869
Ames testNon AMES toxic0.8483
CarcinogenicityNon-carcinogens0.8581
BiodegradationReady biodegradable0.6473
Rat acute toxicity2.3244 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9337
hERG inhibition (predictor II)Non-inhibitor0.9158
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-2290000000-396028b52ce4cedbe2bb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05n0-0490000000-529105b5a87b738ed617
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-6900000000-1e7071aa820eeb1c46ba
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-3190000000-efb4ce7028884fa42743
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9320000000-de7c749cb1ef8f00a7c2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-5ea8917f66ef1d382869

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
Organic acids and derivatives
Class
Organic phosphoric acids and derivatives
Sub Class
Phosphate esters
Direct Parent
Monoalkyl phosphates
Alternative Parents
Cyclitols and derivatives / Secondary alcohols / 1,2-diols / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Monoalkyl phosphate / Cyclitol or derivatives / Secondary alcohol / 1,2-diol / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organic oxide / Hydrocarbon derivative
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
phosphoshikimic acid (CHEBI:17052)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
3-phosphoshikimate 1-carboxyvinyltransferase activity
Specific Function
Catalyzes the transfer of the enolpyruvyl moiety of phosphoenolpyruvate (PEP) to the 5-hydroxyl of shikimate-3-phosphate (S3P) to produce enolpyruvyl shikimate-3-phosphate and inorganic phosphate.
Gene Name
aroA
Uniprot ID
P0A6D3
Uniprot Name
3-phosphoshikimate 1-carboxyvinyltransferase
Molecular Weight
46095.29 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
Unknown
General Function
3-phosphoshikimate 1-carboxyvinyltransferase activity
Specific Function
Catalyzes the transfer of the enolpyruvyl moiety of phosphoenolpyruvate (PEP) to the 5-hydroxyl of shikimate-3-phosphate (S3P) to produce enolpyruvyl shikimate-3-phosphate and inorganic phosphate.
Gene Name
aroA
Uniprot ID
Q9S400
Uniprot Name
3-phosphoshikimate 1-carboxyvinyltransferase
Molecular Weight
45765.42 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:26