L-homoarginine
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Identification
- Generic Name
- L-homoarginine
- DrugBank Accession Number
- DB03974
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 188.2275
Monoisotopic: 188.127325776 - Chemical Formula
- C7H16N4O2
- Synonyms
- Homo-L-arginine
- Homoarginine
- N6-(Aminoiminomethyl)-L-lysine
- N6-amidino-L-Lysine
- N6-amidino-Lysine
- External IDs
- NSC 27429
- NSC 88868
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UNitric oxide synthase, endothelial 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
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- L-alpha-amino acids
- Alternative Parents
- Medium-chain fatty acids / Amino fatty acids / Guanidines / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Carboximidamides / Organopnictogen compounds / Organic oxides / Monoalkylamines show 3 more
- Substituents
- Aliphatic acyclic compound / Amine / Amino acid / Amino fatty acid / Carbonyl group / Carboximidamide / Carboxylic acid / Fatty acid / Fatty acyl / Guanidine show 13 more
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- non-proteinogenic L-alpha-amino acid, L-lysine derivative, homoarginine (CHEBI:27747)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- JF751CK38I
- CAS number
- 156-86-5
- InChI Key
- QUOGESRFPZDMMT-YFKPBYRVSA-N
- InChI
- InChI=1S/C7H16N4O2/c8-5(6(12)13)3-1-2-4-11-7(9)10/h5H,1-4,8H2,(H,12,13)(H4,9,10,11)/t5-/m0/s1
- IUPAC Name
- (2S)-2-amino-6-carbamimidamidohexanoic acid
- SMILES
- N[C@@H](CCCCNC(N)=N)C(O)=O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000670
- KEGG Compound
- C01924
- PubChem Compound
- 9085
- PubChem Substance
- 46506308
- ChemSpider
- 8732
- BindingDB
- 50309588
- ChEBI
- 27747
- ChEMBL
- CHEMBL589752
- ZINC
- ZINC000001529320
- PDBe Ligand
- HRG
- PDB Entries
- 1dm7 / 2vdn / 3diq / 4m2e / 5ijr / 5vbl / 5vlk / 5vlp / 5wxf / 5wxo … show 12 more
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 1.58 mg/mL ALOGPS logP -3.7 ALOGPS logP -2.7 Chemaxon logS -2.1 ALOGPS pKa (Strongest Acidic) 2.49 Chemaxon pKa (Strongest Basic) 12.3 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 125.22 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 58.52 m3·mol-1 Chemaxon Polarizability 20.04 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.6941 Blood Brain Barrier + 0.6076 Caco-2 permeable - 0.7228 P-glycoprotein substrate Substrate 0.5 P-glycoprotein inhibitor I Non-inhibitor 0.9889 P-glycoprotein inhibitor II Non-inhibitor 0.8674 Renal organic cation transporter Non-inhibitor 0.7721 CYP450 2C9 substrate Non-substrate 0.787 CYP450 2D6 substrate Non-substrate 0.704 CYP450 3A4 substrate Non-substrate 0.8101 CYP450 1A2 substrate Non-inhibitor 0.8129 CYP450 2C9 inhibitor Non-inhibitor 0.9003 CYP450 2D6 inhibitor Non-inhibitor 0.925 CYP450 2C19 inhibitor Non-inhibitor 0.7873 CYP450 3A4 inhibitor Non-inhibitor 0.9295 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9937 Ames test AMES toxic 0.7175 Carcinogenicity Non-carcinogens 0.9257 Biodegradation Ready biodegradable 0.9261 Rat acute toxicity 1.7827 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.93 hERG inhibition (predictor II) Non-inhibitor 0.9541
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 152.2251149 predictedDarkChem Lite v0.1.0 [M-H]- 152.3503149 predictedDarkChem Lite v0.1.0 [M-H]- 137.66222 predictedDeepCCS 1.0 (2019) [M+H]+ 152.5343149 predictedDarkChem Lite v0.1.0 [M+H]+ 152.7294149 predictedDarkChem Lite v0.1.0 [M+H]+ 141.01003 predictedDeepCCS 1.0 (2019) [M+Na]+ 152.4737149 predictedDarkChem Lite v0.1.0 [M+Na]+ 152.4139149 predictedDarkChem Lite v0.1.0 [M+Na]+ 150.47005 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]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52