1-Allyl-3-Butyl-8-(N-Acetyl-4-Aminobenzyl)-Xanthine
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Identification
- Generic Name
- 1-Allyl-3-Butyl-8-(N-Acetyl-4-Aminobenzyl)-Xanthine
- DrugBank Accession Number
- DB03267
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 395.4549
Monoisotopic: 395.195739691 - Chemical Formula
- C21H25N5O3
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UPhosphoenolpyruvate carboxykinase, cytosolic [GTP] Not Available Humans - 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 xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Imidazopyrimidines
- Sub Class
- Purines and purine derivatives
- Direct Parent
- Xanthines
- Alternative Parents
- 6-oxopurines / Acetanilides / N-acetylarylamines / Alkaloids and derivatives / Pyrimidones / Vinylogous amides / Acetamides / Imidazoles / Heteroaromatic compounds / Ureas show 7 more
- Substituents
- 6-oxopurine / Acetamide / Acetanilide / Alkaloid or derivatives / Anilide / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Carbonyl group show 22 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- XFOWZKUTPKXWIE-UHFFFAOYSA-N
- InChI
- InChI=1S/C21H25N5O3/c1-4-6-12-25-19-18(20(28)26(11-5-2)21(25)29)23-17(24-19)13-15-7-9-16(10-8-15)22-14(3)27/h5,7-10H,2,4,6,11-13H2,1,3H3,(H,22,27)(H,23,24)
- IUPAC Name
- N-(4-{[3-butyl-2,6-dioxo-1-(prop-2-en-1-yl)-2,3,6,7-tetrahydro-1H-purin-8-yl]methyl}phenyl)acetamide
- SMILES
- CCCCN1C2=C(NC(CC3=CC=C(NC(C)=O)C=C3)=N2)C(=O)N(CC=C)C1=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 447076
- PubChem Substance
- 46504813
- ChemSpider
- 394269
- ChEMBL
- CHEMBL120293
- ZINC
- ZINC000015677757
- PDBe Ligand
- TSX
- PDB Entries
- 1m51
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 0.16 mg/mL ALOGPS logP 2.69 ALOGPS logP 2.48 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 7.86 Chemaxon pKa (Strongest Basic) -0.69 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 98.4 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 112 m3·mol-1 Chemaxon Polarizability 42.91 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.8599 Caco-2 permeable - 0.6304 P-glycoprotein substrate Substrate 0.8144 P-glycoprotein inhibitor I Inhibitor 0.721 P-glycoprotein inhibitor II Non-inhibitor 0.6069 Renal organic cation transporter Non-inhibitor 0.7531 CYP450 2C9 substrate Non-substrate 0.7628 CYP450 2D6 substrate Non-substrate 0.8442 CYP450 3A4 substrate Substrate 0.5466 CYP450 1A2 substrate Non-inhibitor 0.7565 CYP450 2C9 inhibitor Non-inhibitor 0.5934 CYP450 2D6 inhibitor Non-inhibitor 0.8871 CYP450 2C19 inhibitor Non-inhibitor 0.5 CYP450 3A4 inhibitor Inhibitor 0.6629 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6336 Ames test Non AMES toxic 0.5898 Carcinogenicity Non-carcinogens 0.8618 Biodegradation Not ready biodegradable 0.996 Rat acute toxicity 2.9272 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6528 hERG inhibition (predictor II) Non-inhibitor 0.714
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0009000000-bac5468f58533009debc Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0029000000-506fa25ac8558f8507bc Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0udj-0009000000-89c3b6bab1173b08218f Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0ikl-0019000000-3cfe5526343758f3ac19 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0v4r-0039000000-08fcb20149250a2bc2fe Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0w91-2095000000-6cbe03d92f0285674389 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]- 196.57861 predictedDeepCCS 1.0 (2019) [M+H]+ 198.9366 predictedDeepCCS 1.0 (2019) [M+Na]+ 205.6083 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Cytosolic phosphoenolpyruvate carboxykinase that catalyzes the reversible decarboxylation and phosphorylation of oxaloacetate (OAA) and acts as the rate-limiting enzyme in gluconeogenesis (PubMed:24863970, PubMed:26971250, PubMed:28216384, PubMed:30193097). Regulates cataplerosis and anaplerosis, the processes that control the levels of metabolic intermediates in the citric acid cycle (PubMed:24863970, PubMed:26971250, PubMed:28216384, PubMed:30193097). At low glucose levels, it catalyzes the cataplerotic conversion of oxaloacetate to phosphoenolpyruvate (PEP), the rate-limiting step in the metabolic pathway that produces glucose from lactate and other precursors derived from the citric acid cycle (PubMed:30193097). At high glucose levels, it catalyzes the anaplerotic conversion of phosphoenolpyruvate to oxaloacetate (PubMed:30193097). Acts as a regulator of formation and maintenance of memory CD8(+) T-cells: up-regulated in these cells, where it generates phosphoenolpyruvate, via gluconeogenesis (By similarity). The resultant phosphoenolpyruvate flows to glycogen and pentose phosphate pathway, which is essential for memory CD8(+) T-cells homeostasis (By similarity). In addition to the phosphoenolpyruvate carboxykinase activity, also acts as a protein kinase when phosphorylated at Ser-90: phosphorylation at Ser-90 by AKT1 reduces the binding affinity to oxaloacetate and promotes an atypical serine protein kinase activity using GTP as donor (PubMed:32322062). The protein kinase activity regulates lipogenesis: upon phosphorylation at Ser-90, translocates to the endoplasmic reticulum and catalyzes phosphorylation of INSIG proteins (INSIG1 and INSIG2), thereby disrupting the interaction between INSIG proteins and SCAP and promoting nuclear translocation of SREBP proteins (SREBF1/SREBP1 or SREBF2/SREBP2) and subsequent transcription of downstream lipogenesis-related genes (PubMed:32322062)
- Specific Function
- carboxylic acid binding
- Gene Name
- PCK1
- Uniprot ID
- P35558
- Uniprot Name
- Phosphoenolpyruvate carboxykinase, cytosolic [GTP]
- Molecular Weight
- 69193.975 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52