5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol
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Identification
- Generic Name
- 5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol
- DrugBank Accession Number
- DB08466
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 230.2592
Monoisotopic: 230.094294314 - Chemical Formula
- C14H14O3
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ALeukotriene A-4 hydrolase 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 stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Stilbenes
- Sub Class
- Not Available
- Direct Parent
- Stilbenes
- Alternative Parents
- Resorcinols / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Organooxygen compounds / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homomonocyclic compound / Benzenoid / Hydrocarbon derivative / Monocyclic benzene moiety / Organic oxygen compound / Organooxygen compound / Phenol / Resorcinol
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- stilbenol (CHEBI:4582) / Diphenyl ethers, biphenyls, dibenzyls and stilbenes, Bibenzyls (C10255) / Diphenyl ethers, biphenyls, dibenzyls and stilbenes (LMPK13090035)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- CBY43AY0TT
- CAS number
- Not Available
- InChI Key
- HITJFUSPLYBJPE-UHFFFAOYSA-N
- InChI
- InChI=1S/C14H14O3/c15-12-5-3-10(4-6-12)1-2-11-7-13(16)9-14(17)8-11/h3-9,15-17H,1-2H2
- IUPAC Name
- 5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol
- SMILES
- OC1=CC=C(CCC2=CC(O)=CC(O)=C2)C=C1
References
- General References
- Not Available
- External Links
- KEGG Compound
- C10255
- PubChem Compound
- 185914
- PubChem Substance
- 99444937
- ChemSpider
- 161607
- BindingDB
- 50085531
- ChEBI
- 4582
- ChEMBL
- CHEMBL111234
- ZINC
- ZINC000000899123
- PDBe Ligand
- RE2
- PDB Entries
- 3ftu / 3ftx
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 0.0812 mg/mL ALOGPS logP 2.45 ALOGPS logP 3.6 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 9.3 Chemaxon pKa (Strongest Basic) -5.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 60.69 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 66.34 m3·mol-1 Chemaxon Polarizability 24.87 Å3 Chemaxon Number of Rings 2 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 + 0.9503 Blood Brain Barrier + 0.6823 Caco-2 permeable + 0.8604 P-glycoprotein substrate Non-substrate 0.6206 P-glycoprotein inhibitor I Non-inhibitor 0.9594 P-glycoprotein inhibitor II Non-inhibitor 0.7697 Renal organic cation transporter Non-inhibitor 0.7676 CYP450 2C9 substrate Non-substrate 0.7256 CYP450 2D6 substrate Non-substrate 0.8981 CYP450 3A4 substrate Non-substrate 0.6629 CYP450 1A2 substrate Inhibitor 0.7749 CYP450 2C9 inhibitor Inhibitor 0.742 CYP450 2D6 inhibitor Non-inhibitor 0.8326 CYP450 2C19 inhibitor Inhibitor 0.8434 CYP450 3A4 inhibitor Inhibitor 0.7201 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8114 Ames test Non AMES toxic 0.8553 Carcinogenicity Non-carcinogens 0.8488 Biodegradation Not ready biodegradable 0.8105 Rat acute toxicity 1.6999 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7667 hERG inhibition (predictor II) Non-inhibitor 0.8962
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0adi-3920000000-719fe242334d208b9ba6 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0089-2970000000-b3b2c01ab0c78026797d Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0090000000-93bf716daaf8ff05e995 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0pdi-2930000000-f718c92dcbd0493230c9 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00bl-3950000000-8e9126057af3baa7251d Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-7900000000-3cda1b5d4a1ec992711c Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00kf-5900000000-4c33b1b9690d81a560b4 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]- 162.9737984 predictedDarkChem Lite v0.1.0 [M-H]- 152.19347 predictedDeepCCS 1.0 (2019) [M+H]+ 165.6007984 predictedDarkChem Lite v0.1.0 [M+H]+ 154.57365 predictedDeepCCS 1.0 (2019) [M+Na]+ 162.0817984 predictedDarkChem Lite v0.1.0 [M+Na]+ 160.6446 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsLeukotriene A-4 hydrolase
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Bifunctional zinc metalloenzyme that comprises both epoxide hydrolase (EH) and aminopeptidase activities. Acts as an epoxide hydrolase to catalyze the conversion of LTA4 to the pro-inflammatory mediator leukotriene B4 (LTB4) (PubMed:11917124, PubMed:12207002, PubMed:15078870, PubMed:18804029, PubMed:1897988, PubMed:1975494, PubMed:2244921). Has also aminopeptidase activity, with high affinity for N-terminal arginines of various synthetic tripeptides (PubMed:18804029, PubMed:20813919). In addition to its pro-inflammatory EH activity, may also counteract inflammation by its aminopeptidase activity, which inactivates by cleavage another neutrophil attractant, the tripeptide Pro-Gly-Pro (PGP), a bioactive fragment of collagen generated by the action of matrix metalloproteinase-9 (MMP9) and prolylendopeptidase (PREPL) (PubMed:20813919, PubMed:24591641). Involved also in the biosynthesis of resolvin E1 and 18S-resolvin E1 from eicosapentaenoic acid, two lipid mediators that show potent anti-inflammatory and pro-resolving actions (PubMed:21206090)
- Specific Function
- aminopeptidase activity
- Gene Name
- LTA4H
- Uniprot ID
- P09960
- Uniprot Name
- Leukotriene A-4 hydrolase
- Molecular Weight
- 69284.64 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 21:32 / Updated at August 26, 2024 19:22