Phloretic acid
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Identification
- Generic Name
- Phloretic acid
- DrugBank Accession Number
- DB03897
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 166.1739
Monoisotopic: 166.062994186 - Chemical Formula
- C9H10O3
- Synonyms
- 3-(4-Hydroxyphenyl)propionic acid
- 3-(p-hydroxyphenyl)propionic acid
- 4-Hydroxyphenylpropionic acid
- Desaminotyrosine
- Dihydro-p-coumaric acid
- Hydroxyphenyl propionic acid
- p-Hydroxyhydrocinnamic acid
- p-hydroxyphenylpropionic acid
- Phloretic acid
- Phloretinic acid
- β-(p-hydroxyphenyl)propionic acid
- External IDs
- NSC-40949
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UTyrosine phenol-lyase Not Available Citrobacter freundii UPrephenate dehydrogenase Not Available Aquifex aeolicus (strain VF5) UTyrosine phenol-lyase Not Available Escherichia intermedia - 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 phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Phenylpropanoic acids
- Sub Class
- Not Available
- Direct Parent
- Phenylpropanoic acids
- Alternative Parents
- 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 3-phenylpropanoic-acid / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Monocyclic benzene moiety
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- hydroxy monocarboxylic acid (CHEBI:32980)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 6QNC6P18SR
- CAS number
- 501-97-3
- InChI Key
- NMHMNPHRMNGLLB-UHFFFAOYSA-N
- InChI
- InChI=1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12)
- IUPAC Name
- 3-(4-hydroxyphenyl)propanoic acid
- SMILES
- OC(=O)CCC1=CC=C(O)C=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0002199
- KEGG Compound
- C01744
- PubChem Compound
- 10394
- PubChem Substance
- 46504920
- ChemSpider
- 9965
- BindingDB
- 231636
- ChEBI
- 32980
- ChEMBL
- CHEMBL1172560
- ZINC
- ZINC000008383206
- PDBe Ligand
- HPP
- Wikipedia
- Phloretic_acid
- PDB Entries
- 2tpl / 3ggp / 5sxf / 5whl
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 2.71 mg/mL ALOGPS logP 1.15 ALOGPS logP 1.75 Chemaxon logS -1.8 ALOGPS pKa (Strongest Acidic) 4.21 Chemaxon pKa (Strongest Basic) -6 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 57.53 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 43.95 m3·mol-1 Chemaxon Polarizability 16.97 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 + 0.9789 Blood Brain Barrier + 0.5264 Caco-2 permeable + 0.7259 P-glycoprotein substrate Non-substrate 0.6677 P-glycoprotein inhibitor I Non-inhibitor 0.976 P-glycoprotein inhibitor II Non-inhibitor 0.9753 Renal organic cation transporter Non-inhibitor 0.8951 CYP450 2C9 substrate Non-substrate 0.8217 CYP450 2D6 substrate Non-substrate 0.903 CYP450 3A4 substrate Non-substrate 0.7114 CYP450 1A2 substrate Non-inhibitor 0.944 CYP450 2C9 inhibitor Non-inhibitor 0.9796 CYP450 2D6 inhibitor Non-inhibitor 0.9731 CYP450 2C19 inhibitor Non-inhibitor 0.9212 CYP450 3A4 inhibitor Non-inhibitor 0.94 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9615 Ames test Non AMES toxic 0.9434 Carcinogenicity Non-carcinogens 0.9148 Biodegradation Ready biodegradable 0.8949 Rat acute toxicity 1.9895 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8951 hERG inhibition (predictor II) Non-inhibitor 0.9547
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 139.4078379 predictedDarkChem Lite v0.1.0 [M-H]- 139.1901379 predictedDarkChem Lite v0.1.0 [M-H]- 139.3075379 predictedDarkChem Lite v0.1.0 [M-H]- 132.4182 predictedDeepCCS 1.0 (2019) [M+H]+ 140.2175379 predictedDarkChem Lite v0.1.0 [M+H]+ 138.9740379 predictedDarkChem Lite v0.1.0 [M+H]+ 138.9689379 predictedDarkChem Lite v0.1.0 [M+H]+ 135.36142 predictedDeepCCS 1.0 (2019) [M+Na]+ 138.4594379 predictedDarkChem Lite v0.1.0 [M+Na]+ 138.6474379 predictedDarkChem Lite v0.1.0 [M+Na]+ 138.5315379 predictedDarkChem Lite v0.1.0 [M+Na]+ 144.8766 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsTyrosine phenol-lyase
- Kind
- Protein
- Organism
- Citrobacter freundii
- Pharmacological action
- Unknown
- General Function
- Tyrosine phenol-lyase activity
- Specific Function
- Not Available
- Gene Name
- tpl
- Uniprot ID
- P31013
- Uniprot Name
- Tyrosine phenol-lyase
- Molecular Weight
- 51499.525 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]
2. DetailsPrephenate dehydrogenase
- Kind
- Protein
- Organism
- Aquifex aeolicus (strain VF5)
- Pharmacological action
- Unknown
- General Function
- Prephenate dehydrogenase activity
- Specific Function
- Not Available
- Gene Name
- tyrA
- Uniprot ID
- O67636
- Uniprot Name
- Prephenate dehydrogenase
- Molecular Weight
- 34849.26 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]
3. DetailsTyrosine phenol-lyase
- Kind
- Protein
- Organism
- Escherichia intermedia
- Pharmacological action
- Unknown
- General Function
- Tyrosine phenol-lyase activity
- Specific Function
- Not Available
- Gene Name
- tpl
- Uniprot ID
- P31012
- Uniprot Name
- Tyrosine phenol-lyase
- Molecular Weight
- 51441.485 Da
References
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52