L-N(omega)-nitroarginine-(4R)-amino-L-proline amide
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Identification
- Generic Name
- L-N(omega)-nitroarginine-(4R)-amino-L-proline amide
- DrugBank Accession Number
- DB02077
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 330.3436
Monoisotopic: 330.176401232 - Chemical Formula
- C11H22N8O4
- Synonyms
- Not Available
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 proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Proline and derivatives
- Alternative Parents
- Alpha amino acid amides / Pyrrolidinecarboxamides / Nitroguanidines / N-acyl amines / Nitramines / Secondary carboxylic acid amides / Primary carboxylic acid amides / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Carboximidamides show 7 more
- Substituents
- Aliphatic heteromonocyclic compound / Allyl-type 1,3-dipolar organic compound / Alpha-amino acid amide / Amine / Azacycle / Carbonyl group / Carboxamide group / Carboximidamide / Fatty acyl / Fatty amide show 26 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- IUFRDGFKAVLPFZ-CSMHCCOUSA-N
- InChI
- InChI=1S/C11H22N8O4/c12-7(2-1-3-15-11(14)18-19(22)23)10(21)17-6-4-8(9(13)20)16-5-6/h6-8,16H,1-5,12H2,(H2,13,20)(H,17,21)(H3,14,15,18)/t6-,7+,8+/m1/s1
- IUPAC Name
- (2S,4R)-4-[(2S)-2-amino-5-[(E)-[amino(nitroamino)methylidene]amino]pentanamido]pyrrolidine-2-carboxamide
- SMILES
- N[C@@H](CCC\N=C(/N)N[N+]([O-])=O)C(=O)N[C@H]1CN[C@@H](C1)C(N)=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 656912
- PubChem Substance
- 46507698
- ChemSpider
- 571161
- BindingDB
- 50138976
- ChEMBL
- CHEMBL228077
- ZINC
- ZINC000013531446
- PDBe Ligand
- DP9
- PDB Entries
- 1p6j / 1p6n / 1zzq / 1zzr / 1zzs / 1zzt
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 0.424 mg/mL ALOGPS logP -2 ALOGPS logP -3.6 Chemaxon logS -2.9 ALOGPS pKa (Strongest Acidic) 10.82 Chemaxon pKa (Strongest Basic) 8.99 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 9 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 203.79 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 79.27 m3·mol-1 Chemaxon Polarizability 32.56 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 0 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 - 0.8817 Blood Brain Barrier + 0.7548 Caco-2 permeable - 0.6381 P-glycoprotein substrate Substrate 0.5934 P-glycoprotein inhibitor I Non-inhibitor 0.9314 P-glycoprotein inhibitor II Non-inhibitor 0.9417 Renal organic cation transporter Non-inhibitor 0.838 CYP450 2C9 substrate Non-substrate 0.8241 CYP450 2D6 substrate Non-substrate 0.8017 CYP450 3A4 substrate Non-substrate 0.6534 CYP450 1A2 substrate Non-inhibitor 0.795 CYP450 2C9 inhibitor Non-inhibitor 0.8259 CYP450 2D6 inhibitor Non-inhibitor 0.8964 CYP450 2C19 inhibitor Non-inhibitor 0.7849 CYP450 3A4 inhibitor Non-inhibitor 0.8707 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9694 Ames test AMES toxic 0.7612 Carcinogenicity Non-carcinogens 0.866 Biodegradation Ready biodegradable 0.8775 Rat acute toxicity 2.5363 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8174 hERG inhibition (predictor II) Non-inhibitor 0.7411
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0h7r-9870000000-b7e7caf0bae462434092 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]- 160.2751 predictedDeepCCS 1.0 (2019) [M+H]+ 162.56258 predictedDeepCCS 1.0 (2019) [M+Na]+ 170.37129 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