(2S)-2-(biphenyl-4-yloxy)-3-phenylpropanoic acid
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Identification
- Generic Name
- (2S)-2-(biphenyl-4-yloxy)-3-phenylpropanoic acid
- DrugBank Accession Number
- DB08121
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 318.3658
Monoisotopic: 318.125594442 - Chemical Formula
- C21H18O3
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism APeroxisome proliferator-activated receptor gamma inhibitorHumans - 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
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Biphenyls and derivatives
- Direct Parent
- Biphenyls and derivatives
- Alternative Parents
- Phenylpropanoic acids / Phenoxyacetic acid derivatives / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- 3-phenylpropanoic-acid / Alkyl aryl ether / Aromatic homomonocyclic compound / Biphenyl / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Ether / Hydrocarbon derivative / Monocarboxylic acid or derivatives
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- TZTPJJNNACUQQR-FQEVSTJZSA-N
- InChI
- InChI=1S/C21H18O3/c22-21(23)20(15-16-7-3-1-4-8-16)24-19-13-11-18(12-14-19)17-9-5-2-6-10-17/h1-14,20H,15H2,(H,22,23)/t20-/m0/s1
- IUPAC Name
- (2S)-2-{[1,1'-biphenyl]-4-yloxy}-3-phenylpropanoic acid
- SMILES
- [H][C@@](CC1=CC=CC=C1)(OC1=CC=C(C=C1)C1=CC=CC=C1)C(O)=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 11483970
- PubChem Substance
- 99444592
- ChemSpider
- 9658790
- BindingDB
- 28759
- ChEMBL
- CHEMBL191275
- ZINC
- ZINC000013671695
- PDBe Ligand
- LRG
- PDB Entries
- 3b3k / 3d6d / 4l96 / 4l98 / 8hhp
Clinical Trials
- Clinical Trials
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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 0.00112 mg/mL ALOGPS logP 4.5 ALOGPS logP 5.17 Chemaxon logS -5.4 ALOGPS pKa (Strongest Acidic) 4 Chemaxon pKa (Strongest Basic) -4.9 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.53 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 92.85 m3·mol-1 Chemaxon Polarizability 34.71 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9958 Blood Brain Barrier + 0.8563 Caco-2 permeable + 0.6069 P-glycoprotein substrate Non-substrate 0.7156 P-glycoprotein inhibitor I Non-inhibitor 0.7009 P-glycoprotein inhibitor II Non-inhibitor 0.5739 Renal organic cation transporter Non-inhibitor 0.8692 CYP450 2C9 substrate Non-substrate 0.7895 CYP450 2D6 substrate Non-substrate 0.9228 CYP450 3A4 substrate Non-substrate 0.68 CYP450 1A2 substrate Non-inhibitor 0.8034 CYP450 2C9 inhibitor Non-inhibitor 0.8134 CYP450 2D6 inhibitor Non-inhibitor 0.974 CYP450 2C19 inhibitor Non-inhibitor 0.7567 CYP450 3A4 inhibitor Non-inhibitor 0.9626 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7523 Ames test Non AMES toxic 0.9434 Carcinogenicity Non-carcinogens 0.845 Biodegradation Not ready biodegradable 0.612 Rat acute toxicity 2.3025 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9797 hERG inhibition (predictor II) Non-inhibitor 0.8952
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00dl-8911000000-52ff9c209ec3ad8bfaf9 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00xr-0986000000-266b067ae287a090f526 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-01b9-1985000000-b13ed7db058729de3d81 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0g4i-0923000000-1009adbef0991ae75a86 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0uk9-1911000000-d014a2f96fdb56fee061 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0910000000-2066e48d62ddc6f08f93 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0uxr-0900000000-33fb4cc67ced58889ec8 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]- 171.35823 predictedDeepCCS 1.0 (2019) [M+H]+ 173.7162 predictedDeepCCS 1.0 (2019) [M+Na]+ 180.68755 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE) and modulates the transcription of its target genes, such as acyl-CoA oxidase. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis. ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer. Acts as a critical regulator of gut homeostasis by suppressing NF-kappa-B-mediated pro-inflammatory responses. Plays a role in the regulation of cardiovascular circadian rhythms by regulating the transcription of BMAL1 in the blood vessels (By similarity)
- Specific Function
- alpha-actinin binding
- Gene Name
- PPARG
- Uniprot ID
- P37231
- Uniprot Name
- Peroxisome proliferator-activated receptor gamma
- Molecular Weight
- 57619.58 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]
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at September 15, 2010 21:28 / Updated at August 26, 2024 19:22