nor-NOHA

Identification

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Name
nor-NOHA
Accession Number
DB02381  (EXPT02371, DB12913)
Type
Small Molecule
Groups
Investigational
Description

N-Hydroxy-nor-L-arginine (nor-NOHA) is under investigation in clinical trial NCT02009527 (Arginase Inhibition in Ischemia-reperfusion Injury).

Structure
Thumb
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
Categories
Not Available
UNII
U0F1149OFR
CAS number
189302-40-7
Weight
Average: 176.1738
Monoisotopic: 176.09094027
Chemical Formula
C5H12N4O3
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-(1-hydroxycarbamimidamido)butanoic acid
SMILES
N[C@@H](CCNC(=N)NO)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UArginase-1Not AvailableHumans
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
446124
PubChem Substance
46505343
ChemSpider
393563
BindingDB
50008099
ChEMBL
CHEMBL1234777
HET
NNH
PDB Entries
1hqh / 3kv2 / 4iu1 / 4q3u

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedBasic ScienceCoronary Artery Disease / Type 2 Diabetes Mellitus1

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
PropertyValueSource
Water Solubility2.24 mg/mLALOGPS
logP-3.6ALOGPS
logP-3.7ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)2.08ChemAxon
pKa (Strongest Basic)10.57ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area131.46 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity61.54 m3·mol-1ChemAxon
Polarizability16.73 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9049
Blood Brain Barrier+0.5644
Caco-2 permeable-0.6693
P-glycoprotein substrateNon-substrate0.6016
P-glycoprotein inhibitor INon-inhibitor0.9533
P-glycoprotein inhibitor IINon-inhibitor0.9435
Renal organic cation transporterNon-inhibitor0.8299
CYP450 2C9 substrateNon-substrate0.7866
CYP450 2D6 substrateNon-substrate0.7585
CYP450 3A4 substrateNon-substrate0.7623
CYP450 1A2 substrateNon-inhibitor0.8796
CYP450 2C9 inhibitorNon-inhibitor0.8783
CYP450 2D6 inhibitorNon-inhibitor0.8968
CYP450 2C19 inhibitorNon-inhibitor0.8421
CYP450 3A4 inhibitorNon-inhibitor0.8323
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9857
Ames testAMES toxic0.7725
CarcinogenicityNon-carcinogens0.8281
BiodegradationReady biodegradable0.6976
Rat acute toxicity2.1334 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9613
hERG inhibition (predictor II)Non-inhibitor0.9325
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
L-alpha-amino acid / N-hydroxyguanidine / Fatty acid / Guanidine / Amino acid / Carboxylic acid / Monocarboxylic acid or derivatives / Carboximidamide / Amine / Hydrocarbon derivative
show 11 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Manganese ion binding
Specific Function
Not Available
Gene Name
ARG1
Uniprot ID
P05089
Uniprot Name
Arginase-1
Molecular Weight
34734.655 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. 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. [PubMed:17016423]
  3. 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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on June 04, 2019 05:33