Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- FR221647
- DrugBank Accession Number
- DB02096
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for FR221647 (DB02096)
- Weight
- Average: 259.3037
Monoisotopic: 259.132076803 - Chemical Formula
- C14H17N3O2
- Synonyms
- 1-[(2R)-1-hydroxy-4-phenylbutan-2-yl]-1H-imidazole-4-carboxamide
- External IDs
- FR-221647
- FR221647
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism AAdenosine deaminase 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 2-heteroaryl carboxamides. These are compounds containing a heteroaromatic ring that carries a carboxamide group.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Carboxylic acid derivatives
- Direct Parent
- 2-heteroaryl carboxamides
- Alternative Parents
- Carbonylimidazoles / N-substituted imidazoles / Benzene and substituted derivatives / Vinylogous amides / Heteroaromatic compounds / Primary carboxylic acid amides / Azacyclic compounds / Primary alcohols / Organopnictogen compounds / Organonitrogen compounds show 2 more
- Substituents
- 2-heteroaryl carboxamide / Alcohol / Aromatic heteromonocyclic compound / Azacycle / Azole / Benzenoid / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Imidazole-4-carbonyl group show 12 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 4Z97161Z8Y
- CAS number
- 256461-28-6
- InChI Key
- ZUYUIKKHHBEVHL-GFCCVEGCSA-N
- InChI
- InChI=1S/C14H17N3O2/c15-14(19)13-8-17(10-16-13)12(9-18)7-6-11-4-2-1-3-5-11/h1-5,8,10,12,18H,6-7,9H2,(H2,15,19)/t12-/m1/s1
- IUPAC Name
- 1-[(2R)-1-hydroxy-4-phenylbutan-2-yl]-1H-imidazole-4-carboxamide
- SMILES
- [H][C@](CO)(CCC1=CC=CC=C1)N1C=NC(=C1)C(N)=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 447340
- PubChem Substance
- 46507568
- ChemSpider
- 394470
- ChEMBL
- CHEMBL329433
- PDBe Ligand
- FR2
- PDB Entries
- 1ndw
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 0.644 mg/mL ALOGPS logP 0.86 ALOGPS logP 1.14 Chemaxon logS -2.6 ALOGPS pKa (Strongest Acidic) 13.82 Chemaxon pKa (Strongest Basic) 3.24 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 81.14 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 72.55 m3·mol-1 Chemaxon Polarizability 27.66 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 + 0.9819 Blood Brain Barrier + 0.7375 Caco-2 permeable - 0.7253 P-glycoprotein substrate Non-substrate 0.6846 P-glycoprotein inhibitor I Non-inhibitor 0.9731 P-glycoprotein inhibitor II Non-inhibitor 0.8734 Renal organic cation transporter Non-inhibitor 0.7061 CYP450 2C9 substrate Non-substrate 0.8028 CYP450 2D6 substrate Non-substrate 0.8061 CYP450 3A4 substrate Non-substrate 0.7508 CYP450 1A2 substrate Non-inhibitor 0.8898 CYP450 2C9 inhibitor Non-inhibitor 0.8766 CYP450 2D6 inhibitor Non-inhibitor 0.8449 CYP450 2C19 inhibitor Non-inhibitor 0.8435 CYP450 3A4 inhibitor Non-inhibitor 0.8865 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8806 Ames test Non AMES toxic 0.5778 Carcinogenicity Non-carcinogens 0.9323 Biodegradation Not ready biodegradable 0.5342 Rat acute toxicity 1.8973 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9783 hERG inhibition (predictor II) Non-inhibitor 0.7896
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0006-5950000000-18b4f28870bad3c91ccb Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0090000000-bc8265061c450478722b Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-07d3-2970000000-ed1ec7eacb427e77b167 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0007-0790000000-27814076474040eff754 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-052o-4950000000-d3281766217b1d9d26b7 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-014r-1920000000-3487623a45bf4be0be4c Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9600000000-a34bea9cef01dc5b84df 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]- 153.94606 predictedDeepCCS 1.0 (2019) [M+H]+ 156.30406 predictedDeepCCS 1.0 (2019) [M+Na]+ 162.67838 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Catalyzes the hydrolytic deamination of adenosine and 2-deoxyadenosine (PubMed:16670267, PubMed:23193172, PubMed:26166670, PubMed:8452534, PubMed:9361033). Plays an important role in purine metabolism and in adenosine homeostasis. Modulates signaling by extracellular adenosine, and so contributes indirectly to cellular signaling events. Acts as a positive regulator of T-cell coactivation, by binding DPP4 (PubMed:20959412). Its interaction with DPP4 regulates lymphocyte-epithelial cell adhesion (PubMed:11772392). Enhances dendritic cell immunogenicity by affecting dendritic cell costimulatory molecule expression and cytokines and chemokines secretion (By similarity). Enhances CD4+ T-cell differentiation and proliferation (PubMed:20959412). Acts as a positive modulator of adenosine receptors ADORA1 and ADORA2A, by enhancing their ligand affinity via conformational change (PubMed:23193172). Stimulates plasminogen activation (PubMed:15016824). Plays a role in male fertility (PubMed:21919946, PubMed:26166670). Plays a protective role in early postimplantation embryonic development (By similarity)
- Specific Function
- 2'-deoxyadenosine deaminase activity
- Gene Name
- ADA
- Uniprot ID
- P00813
- Uniprot Name
- Adenosine deaminase
- Molecular Weight
- 40764.13 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 June 13, 2005 13:24 / Updated at August 26, 2024 19:22