NAV

5-(1-Carboxy-1-Phosphonooxy-Ethoxyl)-Shikimate-3-Phosphate

Identification

Generic Name
5-(1-Carboxy-1-Phosphonooxy-Ethoxyl)-Shikimate-3-Phosphate
DrugBank Accession Number
DB03116
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 422.1732
Monoisotopic: 422.001528244
Chemical Formula
C10H16O14P2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U3-phosphoshikimate 1-carboxyvinyltransferaseNot AvailableEscherichia coli (strain K12)
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
QUQKBSPZUVNKIF-JQCUSGDOSA-N
InChI
InChI=1S/C10H16O14P2/c1-10(9(14)15,24-26(19,20)21)22-5-2-4(8(12)13)3-6(7(5)11)23-25(16,17)18/h3,5-7,11H,2H2,1H3,(H,12,13)(H,14,15)(H2,16,17,18)(H2,19,20,21)/t5-,6-,7+,10+/m1/s1
IUPAC Name
(3R,4S,5R)-5-[(1S)-1-carboxy-1-(phosphonooxy)ethoxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid
SMILES
[H][C@]1(CC(=C[C@@]([H])(OP(O)(O)=O)[C@@]1([H])O)C(O)=O)O[C@@](C)(OP(O)(O)=O)C(O)=O

References

General References
Not Available
PubChem Compound
5289376
PubChem Substance
46505941
ChemSpider
4451362
ZINC
ZINC000016052263
PDBe Ligand
SKP
PDB Entries
1q36 / 2o0x

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility7.87 mg/mLALOGPS
logP-1.3ALOGPS
logP-1.6Chemaxon
logS-1.7ALOGPS
pKa (Strongest Acidic)0.72Chemaxon
pKa (Strongest Basic)-3.6Chemaxon
Physiological Charge-6Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count7Chemaxon
Polar Surface Area237.58 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity77.74 m3·mol-1Chemaxon
Polarizability32.55 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5233
Blood Brain Barrier+0.8083
Caco-2 permeable-0.654
P-glycoprotein substrateNon-substrate0.6199
P-glycoprotein inhibitor INon-inhibitor0.5851
P-glycoprotein inhibitor IINon-inhibitor0.9841
Renal organic cation transporterNon-inhibitor0.921
CYP450 2C9 substrateNon-substrate0.8238
CYP450 2D6 substrateNon-substrate0.8519
CYP450 3A4 substrateNon-substrate0.5326
CYP450 1A2 substrateNon-inhibitor0.8872
CYP450 2C9 inhibitorNon-inhibitor0.8809
CYP450 2D6 inhibitorNon-inhibitor0.905
CYP450 2C19 inhibitorNon-inhibitor0.85
CYP450 3A4 inhibitorNon-inhibitor0.9817
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9689
Ames testNon AMES toxic0.8309
CarcinogenicityNon-carcinogens0.8162
BiodegradationNot ready biodegradable0.5947
Rat acute toxicity2.4515 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9192
hERG inhibition (predictor II)Non-inhibitor0.9131
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-MSsplash10-0002-9213100000-63ad8faf4e59c6088f06
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-056r-0039300000-4ff2b7252e863f03fa6d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9164000000-a4aee377e97cd388349c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9122400000-fc529823019e87daf42f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-1920000000-5dc649a0c4080a30a8e7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-1424ae2e341b1d2485ec
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-5920000000-e751f127f054e13ab194
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-158.6137
predicted
DeepCCS 1.0 (2019)
[M+H]+160.89537
predicted
DeepCCS 1.0 (2019)
[M+Na]+166.80789
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 3-phosphoshikimate 1-carboxyvinyltransferase
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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52