NAV

N(5)-[(hydroxyamino)(imino)methyl]-L-ornithine

Identification

Generic Name
N(5)-[(hydroxyamino)(imino)methyl]-L-ornithine
DrugBank Accession Number
DB03144
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 190.2004
Monoisotopic: 190.106590334
Chemical Formula
C6H14N4O3
Synonyms
  • N-omega-hydroxy-L-arginine
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNitric oxide synthase, endothelialNot AvailableHumans
UNitric oxide synthase oxygenaseNot AvailableBacillus subtilis (strain 168)
UNitric oxide synthase, inducibleNot AvailableHumans
UArginase-1Not AvailableHumans
UNitric oxide synthase, brainNot 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

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Arginine: Glycine Amidinotransferase Deficiency (AGAT Deficiency)Disease
Creatine Deficiency, Guanidinoacetate Methyltransferase DeficiencyDisease
Hyperornithinemia with Gyrate Atrophy (HOGA)Disease
Prolidase Deficiency (PD)Disease
Prolinemia Type IIDisease
Ornithine Aminotransferase Deficiency (OAT Deficiency)Disease
Hyperornithinemia-Hyperammonemia-Homocitrullinuria [HHH-syndrome]Disease
Arginine and Proline MetabolismMetabolic
Guanidinoacetate Methyltransferase Deficiency (GAMT Deficiency)Disease
Hyperprolinemia Type IIDisease
Hyperprolinemia Type IDisease
L-Arginine:Glycine Amidinotransferase DeficiencyDisease
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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 arginine and derivatives. These are compounds containing arginine or a derivative thereof resulting from reaction of arginine 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
Arginine and derivatives
Alternative Parents
L-alpha-amino acids / N-hydroxyguanidines / Fatty acids and conjugates / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Carboximidamides / Organopnictogen compounds / Organic oxides / Monoalkylamines
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Substituents
Aliphatic acyclic compound / Alpha-amino acid / Amine / Amino acid / Arginine or derivatives / Carbonyl group / Carboximidamide / Carboxylic acid / Fatty acid / Guanidine
show 13 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
N(omega)-hydroxy-L-arginine, N(5)-[(hydroxyamino)(imino)methyl]ornithine (CHEBI:43088)
Affected organisms
Not Available

Chemical Identifiers

UNII
J2FGL272NZ
CAS number
Not Available
InChI Key
FQWRAVYMZULPNK-BYPYZUCNSA-N
InChI
InChI=1S/C6H14N4O3/c7-4(5(11)12)2-1-3-9-6(8)10-13/h4,13H,1-3,7H2,(H,11,12)(H3,8,9,10)/t4-/m0/s1
IUPAC Name
(2S)-2-amino-5-(N'-hydroxycarbamimidamido)pentanoic acid
SMILES
N[C@@H](CCCNC(=N)NO)C(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0004224
PubChem Compound
123895
PubChem Substance
46506099
ChemSpider
110427
BindingDB
50230418
ChEBI
43088
ChEMBL
CHEMBL260629
ZINC
ZINC000004096974
PDBe Ligand
HAR
PDB Entries
1dwv / 1dww / 1dwx / 1hqf / 1lzx / 1m7z / 2fbz / 2fc2 / 3hsn / 3hso …
show 9 more

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

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 Solubility1.49 mg/mLALOGPS
logP-3.6ALOGPS
logP-3.3Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)2.2Chemaxon
pKa (Strongest Basic)10.48Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area131.46 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity66.18 m3·mol-1Chemaxon
Polarizability19.04 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9361
Blood Brain Barrier+0.7575
Caco-2 permeable-0.6781
P-glycoprotein substrateNon-substrate0.5869
P-glycoprotein inhibitor INon-inhibitor0.9666
P-glycoprotein inhibitor IINon-inhibitor0.9664
Renal organic cation transporterNon-inhibitor0.8227
CYP450 2C9 substrateNon-substrate0.8154
CYP450 2D6 substrateNon-substrate0.7636
CYP450 3A4 substrateNon-substrate0.7751
CYP450 1A2 substrateNon-inhibitor0.9086
CYP450 2C9 inhibitorNon-inhibitor0.8906
CYP450 2D6 inhibitorNon-inhibitor0.9196
CYP450 2C19 inhibitorNon-inhibitor0.8547
CYP450 3A4 inhibitorNon-inhibitor0.8345
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9905
Ames testAMES toxic0.809
CarcinogenicityNon-carcinogens0.8161
BiodegradationReady biodegradable0.6516
Rat acute toxicity2.0835 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9437
hERG inhibition (predictor II)Non-inhibitor0.9485
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-MSsplash10-00dl-9300000000-c0d34ab8e133be65558a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00r6-3900000000-fcc8f79a2cde4b716e2f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-d5382a1ec67a04c738c7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9200000000-028d5bbf0dff5e143de6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ox-8900000000-d881fd22d407081f8e76
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-9000000000-cf1fd19619b616122b27
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-9000000000-6ad3e9fed753b48e6e11
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-136.04979
predicted
DeepCCS 1.0 (2019)
[M+H]+139.35197
predicted
DeepCCS 1.0 (2019)
[M+Na]+148.81676
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Nitric 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]
  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. [Article]
Details2. Nitric oxide synthase oxygenase
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
Nitric-oxide synthase activity
Specific Function
Catalyzes the production of nitric oxide.
Gene Name
nos
Uniprot ID
O34453
Uniprot Name
Nitric oxide synthase oxygenase
Molecular Weight
41902.9 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. [Article]
  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. [Article]
Details3. Nitric oxide synthase, inducible
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 macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity ...
Gene Name
NOS2
Uniprot ID
P35228
Uniprot Name
Nitric oxide synthase, inducible
Molecular Weight
131116.3 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. [Article]
  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. [Article]
  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. [Article]
Details4. Arginase-1
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. [Article]
  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. [Article]
  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. [Article]
Details5. Nitric 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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52