nor-NOHA
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Explore a selection of our essential drug information below, or:
Overview
- DrugBank ID
- DB02381
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 1
- Phase 2
- 0
- Phase 3
- 0
- Phase 4
- 0
- Mechanism of Action
- Arginase-2, mitochondrialInhibitor
- Arginase-2, mitochondrial
Identification
- Generic Name
- nor-NOHA
- DrugBank Accession Number
- DB02381
- Background
N-Hydroxy-nor-L-arginine (nor-NOHA) is under investigation in clinical trial NCT02009527 (Arginase Inhibition in Ischemia-reperfusion Injury).
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 176.1738
Monoisotopic: 176.09094027 - Chemical Formula
- C5H12N4O3
- Synonyms
- (2S)-2-amino-4-(((hydroxyamino)iminomethyl)amino)butanoic acid
- N-hydroxy-nor-arginine
- N-hydroxy-nor-L-arginine
- Nomega-Hydroxy-nor-L-arginine
- External IDs
- J842.499C
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AArginase-2, mitochondrial inhibitorHumans UArginase-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 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
- N-hydroxyguanidines / Fatty acids and conjugates / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Carboximidamides / Organopnictogen compounds / Organic oxides / Monoalkylamines / Imines show 2 more
- Substituents
- Aliphatic acyclic compound / Amine / Amino acid / Carbonyl group / Carboximidamide / Carboxylic acid / Fatty acid / Guanidine / Hydrocarbon derivative / Imine show 11 more
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- U0F1149OFR
- CAS number
- 189302-40-7
- InChI Key
- KOBHCUDVWOTEKO-VKHMYHEASA-N
- InChI
- InChI=1S/C5H12N4O3/c6-3(4(10)11)1-2-8-5(7)9-12/h3,12H,1-2,6H2,(H,10,11)(H3,7,8,9)/t3-/m0/s1
- IUPAC Name
- (2S)-2-amino-4-(N'-hydroxycarbamimidamido)butanoic acid
- SMILES
- N[C@@H](CCNC(=N)NO)C(O)=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 446124
- PubChem Substance
- 46505343
- ChemSpider
- 393563
- BindingDB
- 50008099
- ChEMBL
- CHEMBL1234777
- ZINC
- ZINC000002244322
- PDBe Ligand
- NNH
- PDB Entries
- 1hqh / 3kv2 / 4iu1 / 4q3u / 7xmn
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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 2.24 mg/mL ALOGPS logP -3.6 ALOGPS logP -3.7 Chemaxon logS -1.9 ALOGPS pKa (Strongest Acidic) 2.08 Chemaxon pKa (Strongest Basic) 10.56 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 131.46 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 61.54 m3·mol-1 Chemaxon Polarizability 16.73 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 + 0.9049 Blood Brain Barrier + 0.5644 Caco-2 permeable - 0.6693 P-glycoprotein substrate Non-substrate 0.6016 P-glycoprotein inhibitor I Non-inhibitor 0.9533 P-glycoprotein inhibitor II Non-inhibitor 0.9435 Renal organic cation transporter Non-inhibitor 0.8299 CYP450 2C9 substrate Non-substrate 0.7866 CYP450 2D6 substrate Non-substrate 0.7585 CYP450 3A4 substrate Non-substrate 0.7623 CYP450 1A2 substrate Non-inhibitor 0.8796 CYP450 2C9 inhibitor Non-inhibitor 0.8783 CYP450 2D6 inhibitor Non-inhibitor 0.8968 CYP450 2C19 inhibitor Non-inhibitor 0.8421 CYP450 3A4 inhibitor Non-inhibitor 0.8323 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9857 Ames test AMES toxic 0.7725 Carcinogenicity Non-carcinogens 0.8281 Biodegradation Ready biodegradable 0.6976 Rat acute toxicity 2.1334 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9613 hERG inhibition (predictor II) Non-inhibitor 0.9325
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0543-9300000000-985429ac21264690caca Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-1900000000-f034cfe5346e722f66d6 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0gb9-1900000000-48e51f39c0b5d20eee02 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0pdi-9700000000-85f33c5a401e1dff3c22 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0f6x-9700000000-4bafe0001c6d7e53a27b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4l-9200000000-03511d2aa0350a03f08a Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9000000000-8f6233dcf511512ed61e 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]- 146.7367723 predictedDarkChem Lite v0.1.0 [M-H]- 131.28825 predictedDeepCCS 1.0 (2019) [M+H]+ 147.0873723 predictedDarkChem Lite v0.1.0 [M+H]+ 135.11559 predictedDeepCCS 1.0 (2019) [M+Na]+ 147.1780723 predictedDarkChem Lite v0.1.0 [M+Na]+ 144.42111 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsArginase-2, mitochondrial
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- May play a role in the regulation of extra-urea cycle arginine metabolism and also in down-regulation of nitric oxide synthesis. Extrahepatic arginase functions to regulate L-arginine bioavailability to nitric oxid synthase (NOS). Arginine metabolism is a critical regulator of innate and adaptive immune responses. Seems to be involved in negative regulation of the survival capacity of activated CD4(+) and CD8(+) T cells (PubMed:27745970). May suppress inflammation-related signaling in asthmatic airway epithelium (PubMed:27214549). May contribute to the immune evasion of H.pylori by restricting M1 macrophage activation and polyamine metabolism (By similarity). In fetal dendritic cells may play a role in promoting immune suppression and T cell TNF-alpha production during gestation (PubMed:28614294). Regulates RPS6KB1 signaling, which promotes endothelial cell senescence and inflammation and implicates NOS3/eNOS dysfunction (PubMed:22928666). Can inhibit endothelial autophagy independently of its enzymatic activity implicating mTORC2 signaling (PubMed:25484082). Involved in vascular smooth muscle cell senescence and apoptosis independently of its enzymatic activity (PubMed:23832324). Since NOS is found in the penile corpus cavernosum smooth muscle, the clitoral corpus cavernosum and the vagina, arginase-2 plays a role in both male and female sexual arousal (PubMed:12859189)
- Specific Function
- arginase activity
- Gene Name
- ARG2
- Uniprot ID
- P78540
- Uniprot Name
- Arginase-2, mitochondrial
- Molecular Weight
- 38577.515 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
2. DetailsArginase-1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Key element of the urea cycle converting L-arginine to urea and L-ornithine, which is further metabolized into metabolites proline and polyamides that drive collagen synthesis and bioenergetic pathways critical for cell proliferation, respectively; the urea cycle takes place primarily in the liver and, to a lesser extent, in the kidneys
- Specific Function
- arginase activity
- Gene Name
- ARG1
- Uniprot ID
- P05089
- Uniprot Name
- Arginase-1
- Molecular Weight
- 34734.655 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 August 26, 2024 19:22