Shikimate-3-Phosphate
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Identification
- Generic Name
- Shikimate-3-Phosphate
- DrugBank Accession Number
- DB04328
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 254.1312
Monoisotopic: 254.01915384 - Chemical Formula
- C7H11O8P
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism U3-phosphoshikimate 1-carboxyvinyltransferase Not Available Escherichia coli (strain K12) U3-phosphoshikimate 1-carboxyvinyltransferase Not Available Streptococcus 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,2-diol / Alcohol / Aliphatic homomonocyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Cyclitol or derivatives / Hydrocarbon derivative / Monoalkyl phosphate / Monocarboxylic acid or derivatives
- Molecular Framework
- Aliphatic homomonocyclic compounds
- External Descriptors
- phosphoshikimic acid (CHEBI:17052)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- 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[C@@H]1CC(=C[C@@H](OP(O)(O)=O)[C@H]1O)C(O)=O
References
- General References
- Not Available
- External Links
- KEGG Compound
- C03175
- PubChem Compound
- 121947
- PubChem Substance
- 46504914
- ChemSpider
- 108789
- BindingDB
- 100283
- ChEBI
- 17052
- ChEMBL
- CHEMBL95193
- ZINC
- ZINC000003870237
- PDBe Ligand
- S3P
- PDB Entries
- 1g6s / 1g6t / 1mi4 / 1rf6 / 2gg6 / 2gga / 2ggd / 2iyy / 2iyz / 2o0b … show 12 more
Clinical Trials
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
Property Value Source Water Solubility 21.0 mg/mL ALOGPS logP -2.1 ALOGPS logP -1.8 Chemaxon logS -1.1 ALOGPS pKa (Strongest Acidic) 1.32 Chemaxon pKa (Strongest Basic) -3.2 Chemaxon Physiological Charge -3 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 144.52 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 49.83 m3·mol-1 Chemaxon Polarizability 20.57 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.7268 Blood Brain Barrier + 0.7203 Caco-2 permeable - 0.7061 P-glycoprotein substrate Non-substrate 0.601 P-glycoprotein inhibitor I Non-inhibitor 0.7215 P-glycoprotein inhibitor II Non-inhibitor 0.9962 Renal organic cation transporter Non-inhibitor 0.9484 CYP450 2C9 substrate Non-substrate 0.8686 CYP450 2D6 substrate Non-substrate 0.8494 CYP450 3A4 substrate Non-substrate 0.5926 CYP450 1A2 substrate Non-inhibitor 0.8924 CYP450 2C9 inhibitor Non-inhibitor 0.8975 CYP450 2D6 inhibitor Non-inhibitor 0.9019 CYP450 2C19 inhibitor Non-inhibitor 0.8622 CYP450 3A4 inhibitor Non-inhibitor 0.9806 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9869 Ames test Non AMES toxic 0.8483 Carcinogenicity Non-carcinogens 0.8581 Biodegradation Ready biodegradable 0.6473 Rat acute toxicity 2.3244 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9337 hERG inhibition (predictor II) Non-inhibitor 0.9158
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0002-9420000000-24bff48841e0db52f23d Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-014r-0690000000-1d3dc1d2fa049f9bfcc7 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0ufr-5090000000-74a682f15606326217ff Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0fba-9330000000-82585cc26a617dbeed34 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4r-1920000000-533253d07da109ca065b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004j-9200000000-3b05837ce32ecaf5feea Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00li-9300000000-6392322b27a3c4301251 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 144.5109 predictedDeepCCS 1.0 (2019) [M+H]+ 146.90645 predictedDeepCCS 1.0 (2019) [M+Na]+ 152.81898 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- 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
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52