N-{(4S)-4-Amino-5-[(2-aminoethyl)amino]pentyl}-N'-nitroguanidine
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Identification
- Generic Name
- N-{(4S)-4-Amino-5-[(2-aminoethyl)amino]pentyl}-N'-nitroguanidine
- DrugBank Accession Number
- DB02027
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 247.298
Monoisotopic: 247.175672951 - Chemical Formula
- C8H21N7O2
- Synonyms
- 1-{(4S)-4-Amino-5-[(2-aminoethyl)amino]pentyl}-3-nitroguanidine
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UNitric oxide synthase, endothelial Not Available Humans UNitric oxide synthase, brain 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 nitroguanidines. These are organonitrogen compounds containing a nitro group, which is N-linked to a guanidine.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Guanidines
- Direct Parent
- Nitroguanidines
- Alternative Parents
- Nitramines / Propargyl-type 1,3-dipolar organic compounds / Dialkylamines / Carboximidamides / Organopnictogen compounds / Organic zwitterions / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
- Substituents
- Aliphatic acyclic compound / Allyl-type 1,3-dipolar organic compound / Amine / Carboximidamide / Hydrocarbon derivative / Nitramine / Nitroguanidine / Organic 1,3-dipolar compound / Organic nitro compound / Organic oxide
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- 357965-98-1
- InChI Key
- RMSWBHUVFNFNIZ-ZETCQYMHSA-N
- InChI
- InChI=1S/C8H21N7O2/c9-3-5-12-6-7(10)2-1-4-13-8(11)14-15(16)17/h7,12H,1-6,9-10H2,(H3,11,13,14)/t7-/m0/s1
- IUPAC Name
- N'-[(4S)-4-amino-5-[(2-aminoethyl)amino]pentyl]-N-nitroguanidine
- SMILES
- NCCNC[C@@H](N)CCCNC(=N)N[N+]([O-])=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 656911
- PubChem Substance
- 46504827
- ChemSpider
- 571160
- BindingDB
- 21960
- ChEMBL
- CHEMBL227937
- ZINC
- ZINC000001662969
- PDBe Ligand
- DP3
- PDB Entries
- 1p6i / 1p6m
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 0.338 mg/mL ALOGPS logP -1.4 ALOGPS logP -2.5 Chemaxon logS -2.9 ALOGPS pKa (Strongest Acidic) 10.98 Chemaxon pKa (Strongest Basic) 9.94 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 155.12 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 74.42 m3·mol-1 Chemaxon Polarizability 25.97 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7614 Blood Brain Barrier + 0.7658 Caco-2 permeable - 0.5863 P-glycoprotein substrate Substrate 0.5366 P-glycoprotein inhibitor I Non-inhibitor 0.9295 P-glycoprotein inhibitor II Non-inhibitor 0.9405 Renal organic cation transporter Non-inhibitor 0.7153 CYP450 2C9 substrate Non-substrate 0.8917 CYP450 2D6 substrate Non-substrate 0.7677 CYP450 3A4 substrate Non-substrate 0.7287 CYP450 1A2 substrate Non-inhibitor 0.838 CYP450 2C9 inhibitor Non-inhibitor 0.8482 CYP450 2D6 inhibitor Non-inhibitor 0.9005 CYP450 2C19 inhibitor Non-inhibitor 0.8375 CYP450 3A4 inhibitor Non-inhibitor 0.9418 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9763 Ames test AMES toxic 0.858 Carcinogenicity Non-carcinogens 0.6753 Biodegradation Not ready biodegradable 0.586 Rat acute toxicity 2.4278 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.8309 hERG inhibition (predictor II) Non-inhibitor 0.8151
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0uk9-4900000000-c7302880b27b1b01fb24 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]- 164.918137 predictedDarkChem Lite v0.1.0 [M-H]- 148.85039 predictedDeepCCS 1.0 (2019) [M+H]+ 165.347937 predictedDarkChem Lite v0.1.0 [M+H]+ 152.20506 predictedDeepCCS 1.0 (2019) [M+Na]+ 165.285237 predictedDarkChem Lite v0.1.0 [M+Na]+ 160.41734 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsNitric oxide synthase, endothelial
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Tetrahydrobiopterin binding
- Specific Function
- Produces nitric oxide (NO) which is implicated in vascular smooth muscle relaxation through a cGMP-mediated signal transduction pathway. NO mediates vascular endothelial growth factor (VEGF)-induce...
- Gene Name
- NOS3
- Uniprot ID
- P29474
- Uniprot Name
- Nitric oxide synthase, endothelial
- Molecular Weight
- 133287.62 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]
2. DetailsNitric oxide synthase, brain
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Tetrahydrobiopterin binding
- Specific Function
- Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In the brain and peripheral nervous system, NO displays many properties of a neurotransmitter. P...
- Gene Name
- NOS1
- Uniprot ID
- P29475
- Uniprot Name
- Nitric oxide synthase, brain
- Molecular Weight
- 160969.095 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