(2S)-2-(biphenyl-4-yloxy)-3-phenylpropanoic acid

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
TargetActionsOrganism
UPeroxisome proliferator-activated receptor gammaNot AvailableHumans
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
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
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
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 Solubility0.00112 mg/mLALOGPS
logP4.5ALOGPS
logP5.17Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)4Chemaxon
pKa (Strongest Basic)-4.9Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area46.53 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity92.85 m3·mol-1Chemaxon
Polarizability34.71 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9958
Blood Brain Barrier+0.8563
Caco-2 permeable+0.6069
P-glycoprotein substrateNon-substrate0.7156
P-glycoprotein inhibitor INon-inhibitor0.7009
P-glycoprotein inhibitor IINon-inhibitor0.5739
Renal organic cation transporterNon-inhibitor0.8692
CYP450 2C9 substrateNon-substrate0.7895
CYP450 2D6 substrateNon-substrate0.9228
CYP450 3A4 substrateNon-substrate0.68
CYP450 1A2 substrateNon-inhibitor0.8034
CYP450 2C9 inhibitorNon-inhibitor0.8134
CYP450 2D6 inhibitorNon-inhibitor0.974
CYP450 2C19 inhibitorNon-inhibitor0.7567
CYP450 3A4 inhibitorNon-inhibitor0.9626
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7523
Ames testNon AMES toxic0.9434
CarcinogenicityNon-carcinogens0.845
BiodegradationNot ready biodegradable0.612
Rat acute toxicity2.3025 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9797
hERG inhibition (predictor II)Non-inhibitor0.8952
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-MSsplash10-00dl-8911000000-52ff9c209ec3ad8bfaf9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00xr-0986000000-266b067ae287a090f526
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01b9-1985000000-b13ed7db058729de3d81
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0g4i-0923000000-1009adbef0991ae75a86
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uk9-1911000000-d014a2f96fdb56fee061
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0910000000-2066e48d62ddc6f08f93
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uxr-0900000000-33fb4cc67ced58889ec8
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]-171.35823
predicted
DeepCCS 1.0 (2019)
[M+H]+173.7162
predicted
DeepCCS 1.0 (2019)
[M+Na]+180.68755
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific 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...
Gene Name
PPARG
Uniprot ID
P37231
Uniprot Name
Peroxisome proliferator-activated receptor gamma
Molecular Weight
57619.58 Da
References
  1. 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 21:28 / Updated at June 12, 2020 16:52