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Identification
- Generic Name
- 9-Butyl-8-(3-Methoxybenzyl)-9h-Purin-6-Amine
- DrugBank Accession Number
- DB03809
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 9-Butyl-8-(3-Methoxybenzyl)-9h-Purin-6-Amine (DB03809)
- Weight
- Average: 311.3815
Monoisotopic: 311.174610319 - Chemical Formula
- C17H21N5O
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism AHeat shock protein HSP 90-alpha 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 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Imidazopyrimidines
- Sub Class
- Purines and purine derivatives
- Direct Parent
- 6-aminopurines
- Alternative Parents
- Phenoxy compounds / Methoxybenzenes / Anisoles / Aminopyrimidines and derivatives / Alkyl aryl ethers / N-substituted imidazoles / Imidolactams / Heteroaromatic compounds / Azacyclic compounds / Primary amines show 2 more
- Substituents
- 6-aminopurine / Alkyl aryl ether / Amine / Aminopyrimidine / Anisole / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Ether show 16 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
- BWLWUGBHOXIUBP-UHFFFAOYSA-N
- InChI
- InChI=1S/C17H21N5O/c1-3-4-8-22-14(10-12-6-5-7-13(9-12)23-2)21-15-16(18)19-11-20-17(15)22/h5-7,9,11H,3-4,8,10H2,1-2H3,(H2,18,19,20)
- IUPAC Name
- 9-butyl-8-[(3-methoxyphenyl)methyl]-9H-purin-6-amine
- SMILES
- CCCCN1C(CC2=CC=CC(OC)=C2)=NC2=C(N)N=CN=C12
References
- General References
- Not Available
- External Links
- PubChem Compound
- 5289228
- PubChem Substance
- 46506776
- ChemSpider
- 4451231
- BindingDB
- 15376
- ChEMBL
- CHEMBL109612
- ZINC
- ZINC000012503928
- PDBe Ligand
- PU5
- PDB Entries
- 1uy8
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 0.0724 mg/mL ALOGPS logP 3 ALOGPS logP 2.82 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 18.56 Chemaxon pKa (Strongest Basic) 3.71 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 78.85 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 91 m3·mol-1 Chemaxon Polarizability 34.49 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 + 0.9775 Caco-2 permeable + 0.5659 P-glycoprotein substrate Substrate 0.7469 P-glycoprotein inhibitor I Non-inhibitor 0.6931 P-glycoprotein inhibitor II Inhibitor 0.6909 Renal organic cation transporter Inhibitor 0.6605 CYP450 2C9 substrate Non-substrate 0.8664 CYP450 2D6 substrate Non-substrate 0.6237 CYP450 3A4 substrate Substrate 0.633 CYP450 1A2 substrate Inhibitor 0.7795 CYP450 2C9 inhibitor Non-inhibitor 0.6808 CYP450 2D6 inhibitor Inhibitor 0.8703 CYP450 2C19 inhibitor Non-inhibitor 0.5351 CYP450 3A4 inhibitor Inhibitor 0.7671 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8101 Ames test AMES toxic 0.5063 Carcinogenicity Non-carcinogens 0.9429 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6360 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5902 hERG inhibition (predictor II) Inhibitor 0.6415
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0009000000-7e5739642227c7ccadaf Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0249000000-f86c6ccfd3b158759b43 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0019000000-d5a8e797786b0542f681 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0920000000-41bfe95d89d344cd446b Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-01pa-0590000000-f580726c4350339581df Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0019-1930000000-a836ea235eb50a1c7a15 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]- 174.48463 predictedDeepCCS 1.0 (2019) [M+H]+ 176.84262 predictedDeepCCS 1.0 (2019) [M+Na]+ 182.93578 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Molecular chaperone that promotes the maturation, structural maintenance and proper regulation of specific target proteins involved for instance in cell cycle control and signal transduction. Undergoes a functional cycle that is linked to its ATPase activity which is essential for its chaperone activity. This cycle probably induces conformational changes in the client proteins, thereby causing their activation. Interacts dynamically with various co-chaperones that modulate its substrate recognition, ATPase cycle and chaperone function (PubMed:11274138, PubMed:12526792, PubMed:15577939, PubMed:15937123, PubMed:27353360, PubMed:29127155). Engages with a range of client protein classes via its interaction with various co-chaperone proteins or complexes, that act as adapters, simultaneously able to interact with the specific client and the central chaperone itself (PubMed:29127155). Recruitment of ATP and co-chaperone followed by client protein forms a functional chaperone. After the completion of the chaperoning process, properly folded client protein and co-chaperone leave HSP90 in an ADP-bound partially open conformation and finally, ADP is released from HSP90 which acquires an open conformation for the next cycle (PubMed:26991466, PubMed:27295069). Plays a critical role in mitochondrial import, delivers preproteins to the mitochondrial import receptor TOMM70 (PubMed:12526792). Apart from its chaperone activity, it also plays a role in the regulation of the transcription machinery. HSP90 and its co-chaperones modulate transcription at least at three different levels (PubMed:25973397). In the first place, they alter the steady-state levels of certain transcription factors in response to various physiological cues (PubMed:25973397). Second, they modulate the activity of certain epigenetic modifiers, such as histone deacetylases or DNA methyl transferases, and thereby respond to the change in the environment (PubMed:25973397). Third, they participate in the eviction of histones from the promoter region of certain genes and thereby turn on gene expression (PubMed:25973397). Binds bacterial lipopolysaccharide (LPS) and mediates LPS-induced inflammatory response, including TNF secretion by monocytes (PubMed:11276205). Antagonizes STUB1-mediated inhibition of TGF-beta signaling via inhibition of STUB1-mediated SMAD3 ubiquitination and degradation (PubMed:24613385). Mediates the association of TOMM70 with IRF3 or TBK1 in mitochondrial outer membrane which promotes host antiviral response (PubMed:20628368, PubMed:25609812)
- Specific Function
- ATP binding
- Gene Name
- HSP90AA1
- Uniprot ID
- P07900
- Uniprot Name
- Heat shock protein HSP 90-alpha
- Molecular Weight
- 84659.015 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