Identification
- Generic Name
- (4aS)-5-[(2,4-diaminopteridin-6-yl)methyl]-4a,5-dihydro-2H-dibenzo[b,f]azepin-8-ol
- DrugBank Accession Number
- DB08448
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for (4aS)-5-[(2,4-diaminopteridin-6-yl)methyl]-4a,5-dihydro-2H-dibenzo[b,f]azepin-8-ol (DB08448)
- Weight
- Average: 385.4219
Monoisotopic: 385.165108265 - Chemical Formula
- C21H19N7O
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UDihydrofolate reductase 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.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 benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzazepines
- Sub Class
- Not Available
- Direct Parent
- Benzazepines
- Alternative Parents
- Pteridines and derivatives / Dialkylarylamines / Azepines / Aralkylamines / Aminopyrimidines and derivatives / 1-hydroxy-2-unsubstituted benzenoids / Pyrazines / Imidolactams / Heteroaromatic compounds / Azacyclic compounds show 4 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / Amine / Aminopyrimidine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azepine / Benzazepine / Benzenoid / Dialkylarylamine show 14 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
- PCBWLKUEKANDCL-INIZCTEOSA-N
- InChI
- InChI=1S/C21H19N7O/c22-19-18-20(27-21(23)26-19)24-10-14(25-18)11-28-16-4-2-1-3-12(16)5-6-13-9-15(29)7-8-17(13)28/h2-10,16,29H,1,11H2,(H4,22,23,24,26,27)/t16-/m0/s1
- IUPAC Name
- (1S)-2-[(2,4-diaminopteridin-6-yl)methyl]-2-azatricyclo[9.4.0.0^{3,8}]pentadeca-3,5,7,9,11,14-hexaen-6-ol
- SMILES
- [H][C@]12C=CCC=C1C=CC1=CC(O)=CC=C1N2CC1=NC2=C(N)N=C(N)N=C2N=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 46937152
- PubChem Substance
- 99444919
- ChemSpider
- 25058626
- ZINC
- ZINC000039112944
- PDBe Ligand
- Q22
- PDB Entries
- 3d80
Clinical Trials
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 0.188 mg/mL ALOGPS logP 2.44 ALOGPS logP 2.33 Chemaxon logS -3.3 ALOGPS pKa (Strongest Acidic) 10.16 Chemaxon pKa (Strongest Basic) 1.81 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 127.07 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 117.42 m3·mol-1 Chemaxon Polarizability 39.75 Å3 Chemaxon Number of Rings 5 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 + 0.9885 Blood Brain Barrier + 0.9074 Caco-2 permeable + 0.5094 P-glycoprotein substrate Substrate 0.7045 P-glycoprotein inhibitor I Non-inhibitor 0.8064 P-glycoprotein inhibitor II Inhibitor 0.5052 Renal organic cation transporter Inhibitor 0.5136 CYP450 2C9 substrate Non-substrate 0.8844 CYP450 2D6 substrate Non-substrate 0.7647 CYP450 3A4 substrate Non-substrate 0.5337 CYP450 1A2 substrate Non-inhibitor 0.5229 CYP450 2C9 inhibitor Non-inhibitor 0.693 CYP450 2D6 inhibitor Non-inhibitor 0.698 CYP450 2C19 inhibitor Non-inhibitor 0.7394 CYP450 3A4 inhibitor Non-inhibitor 0.6254 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5903 Ames test AMES toxic 0.5092 Carcinogenicity Non-carcinogens 0.9268 Biodegradation Not ready biodegradable 0.9941 Rat acute toxicity 2.5366 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6917 hERG inhibition (predictor II) Non-inhibitor 0.5676
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Nadph binding
- Specific Function
- Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA pre...
- Gene Name
- DHFR
- Uniprot ID
- P00374
- Uniprot Name
- Dihydrofolate reductase
- Molecular Weight
- 21452.61 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]
Drug created at September 15, 2010 21:31 / Updated at June 12, 2020 16:52