Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- 5,6-Dihydro-Benzo[H]Cinnolin-3-Ylamine
- DrugBank Accession Number
- DB04069
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for 5,6-Dihydro-Benzo[H]Cinnolin-3-Ylamine (DB04069)
- Weight
- Average: 197.2358
Monoisotopic: 197.095297367 - Chemical Formula
- C12H11N3
- 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
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Not Available
- Mechanism of action
Target Actions Organism UDeath-associated protein kinase 1 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 naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Naphthalenes
- Sub Class
- Not Available
- Direct Parent
- Naphthalenes
- Alternative Parents
- Aminopyridazines / Imidolactams / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Amine / Aminopyridazine / Aromatic heteropolycyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam / Naphthalene / Organic nitrogen compound / Organoheterocyclic compound
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- QKVREUJWFZJEJK-UHFFFAOYSA-N
- InChI
- InChI=1S/C12H11N3/c13-11-7-9-6-5-8-3-1-2-4-10(8)12(9)15-14-11/h1-4,7H,5-6H2,(H2,13,14)
- IUPAC Name
- 5H,6H-benzo[h]cinnolin-3-amine
- SMILES
- NC1=NN=C2C(CCC3=CC=CC=C23)=C1
References
- General References
- Not Available
- External Links
- PDB Entries
- 1p4f
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 1.8 mg/mL ALOGPS logP 1.76 ALOGPS logP 2.14 Chemaxon logS -2 ALOGPS pKa (Strongest Basic) 4.88 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 51.8 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 61.82 m3·mol-1 Chemaxon Polarizability 21.47 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 No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9862 Blood Brain Barrier + 0.9844 Caco-2 permeable + 0.6876 P-glycoprotein substrate Non-substrate 0.6089 P-glycoprotein inhibitor I Non-inhibitor 0.9259 P-glycoprotein inhibitor II Non-inhibitor 0.9479 Renal organic cation transporter Non-inhibitor 0.7228 CYP450 2C9 substrate Non-substrate 0.8882 CYP450 2D6 substrate Non-substrate 0.8684 CYP450 3A4 substrate Non-substrate 0.7437 CYP450 1A2 substrate Inhibitor 0.8944 CYP450 2C9 inhibitor Non-inhibitor 0.7931 CYP450 2D6 inhibitor Non-inhibitor 0.8195 CYP450 2C19 inhibitor Non-inhibitor 0.616 CYP450 3A4 inhibitor Non-inhibitor 0.5487 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5 Ames test AMES toxic 0.8051 Carcinogenicity Non-carcinogens 0.9159 Biodegradation Not ready biodegradable 0.9913 Rat acute toxicity 2.8383 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8892 hERG inhibition (predictor II) Non-inhibitor 0.8211
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00l7-0900000000-292e9078d8736b64db93 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0900000000-fbf3876178598004988b Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0900000000-648a0801864f3271d9ea Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0900000000-364077cd56b4613efd4d Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-0900000000-1447b64c469d6b2395f8 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0f6x-0900000000-b5aa572c062d1a11b352 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0fbc-1900000000-a41d3eda9e4ba75ebb0e 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]- 147.9130093 predictedDarkChem Lite v0.1.0 [M-H]- 143.40836 predictedDeepCCS 1.0 (2019) [M+H]+ 147.6186093 predictedDarkChem Lite v0.1.0 [M+H]+ 145.80392 predictedDeepCCS 1.0 (2019) [M+Na]+ 148.5533093 predictedDarkChem Lite v0.1.0 [M+Na]+ 152.25478 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Calcium/calmodulin-dependent serine/threonine kinase involved in multiple cellular signaling pathways that trigger cell survival, apoptosis, and autophagy. Regulates both type I apoptotic and type II autophagic cell deaths signal, depending on the cellular setting. The former is caspase-dependent, while the latter is caspase-independent and is characterized by the accumulation of autophagic vesicles. Phosphorylates PIN1 resulting in inhibition of its catalytic activity, nuclear localization, and cellular function. Phosphorylates TPM1, enhancing stress fiber formation in endothelial cells. Phosphorylates STX1A and significantly decreases its binding to STXBP1. Phosphorylates PRKD1 and regulates JNK signaling by binding and activating PRKD1 under oxidative stress. Phosphorylates BECN1, reducing its interaction with BCL2 and BCL2L1 and promoting the induction of autophagy. Phosphorylates TSC2, disrupting the TSC1-TSC2 complex and stimulating mTORC1 activity in a growth factor-dependent pathway. Phosphorylates RPS6, MYL9 and DAPK3. Acts as a signaling amplifier of NMDA receptors at extrasynaptic sites for mediating brain damage in stroke. Cerebral ischemia recruits DAPK1 into the NMDA receptor complex and it phosphorylates GRINB at Ser-1303 inducing injurious Ca(2+) influx through NMDA receptor channels, resulting in an irreversible neuronal death. Required together with DAPK3 for phosphorylation of RPL13A upon interferon-gamma activation which is causing RPL13A involvement in transcript-selective translation inhibition
- Specific Function
- ATP binding
- Gene Name
- DAPK1
- Uniprot ID
- P53355
- Uniprot Name
- Death-associated protein kinase 1
- Molecular Weight
- 160044.615 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