Prephenic acid
Star0
Identification
- Generic Name
- Prephenic acid
- DrugBank Accession Number
- DB08427
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 226.1828
Monoisotopic: 226.047738052 - Chemical Formula
- C10H10O6
- Synonyms
- (1s,4s)-prephenic acid
- cis-1-Carboxy-4-hydroxy-alpha-oxo-2,5-cyclohexadiene-1-propanoic acid
- cis-prephenic acid
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UChorismate mutase AroH Not Available Bacillus subtilis (strain 168) - 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 gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Keto acids and derivatives
- Sub Class
- Gamma-keto acids and derivatives
- Direct Parent
- Gamma-keto acids and derivatives
- Alternative Parents
- Dicarboxylic acids and derivatives / Alpha-keto acids and derivatives / Alpha-hydroxy ketones / Secondary alcohols / Carboxylic acids / Organic oxides / Hydrocarbon derivatives
- Substituents
- Alcohol / Aliphatic homomonocyclic compound / Alpha-hydroxy ketone / Alpha-keto acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dicarboxylic acid or derivatives / Gamma-keto acid / Hydrocarbon derivative
- Molecular Framework
- Aliphatic homomonocyclic compounds
- External Descriptors
- prephenic acid (CHEBI:84387)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Z66B98Z97I
- CAS number
- 126-49-8
- InChI Key
- FPWMCUPFBRFMLH-XGAOUMNUSA-N
- InChI
- InChI=1S/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16)/t6-,10+
- IUPAC Name
- (1s,4s)-1-(2-carboxy-2-oxoethyl)-4-hydroxycyclohexa-2,5-diene-1-carboxylic acid
- SMILES
- [H][C@]1(O)C=C[C@](CC(=O)C(O)=O)(C=C1)C(O)=O
References
- General References
- Not Available
- External Links
- KEGG Compound
- C00254
- PubChem Compound
- 1028
- PubChem Substance
- 99444898
- ChemSpider
- 16735981
- ChEBI
- 84387
- ZINC
- ZINC000100036740
- PDBe Ligand
- PRE
- Wikipedia
- Prephenic_acid
- PDB Entries
- 1com / 3zp7 / 5j6f / 6al9
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 36.0 mg/mL ALOGPS logP -0.31 ALOGPS logP 0.061 Chemaxon logS -0.8 ALOGPS pKa (Strongest Acidic) 2.86 Chemaxon pKa (Strongest Basic) -2.1 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 111.9 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 53.55 m3·mol-1 Chemaxon Polarizability 19.73 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.8824 Blood Brain Barrier + 0.8557 Caco-2 permeable - 0.6835 P-glycoprotein substrate Non-substrate 0.6661 P-glycoprotein inhibitor I Non-inhibitor 0.9217 P-glycoprotein inhibitor II Non-inhibitor 0.9515 Renal organic cation transporter Non-inhibitor 0.9185 CYP450 2C9 substrate Non-substrate 0.848 CYP450 2D6 substrate Non-substrate 0.9213 CYP450 3A4 substrate Non-substrate 0.6495 CYP450 1A2 substrate Non-inhibitor 0.9847 CYP450 2C9 inhibitor Non-inhibitor 0.966 CYP450 2D6 inhibitor Non-inhibitor 0.9601 CYP450 2C19 inhibitor Non-inhibitor 0.968 CYP450 3A4 inhibitor Non-inhibitor 0.909 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.989 Ames test Non AMES toxic 0.9128 Carcinogenicity Non-carcinogens 0.8932 Biodegradation Not ready biodegradable 0.7547 Rat acute toxicity 1.6802 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9888 hERG inhibition (predictor II) Non-inhibitor 0.9778
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 155.3065853 predictedDarkChem Lite v0.1.0 [M-H]- 145.30647 predictedDeepCCS 1.0 (2019) [M+H]+ 155.1875853 predictedDarkChem Lite v0.1.0 [M+H]+ 147.70209 predictedDeepCCS 1.0 (2019) [M+Na]+ 155.2355853 predictedDarkChem Lite v0.1.0 [M+Na]+ 153.61461 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
1. DetailsChorismate mutase AroH
- Kind
- Protein
- Organism
- Bacillus subtilis (strain 168)
- Pharmacological action
- Unknown
- General Function
- Chorismate mutase activity
- Specific Function
- Catalyzes the Claisen rearrangement of chorismate to prephenate. Probably involved in the aromatic amino acid biosynthesis.
- Gene Name
- aroH
- Uniprot ID
- P19080
- Uniprot Name
- Chorismate mutase AroH
- Molecular Weight
- 14516.91 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at September 15, 2010 21:31 / Updated at June 12, 2020 16:52