Identification
NameN-Omega-Hydroxy-L-Arginine
Accession NumberDB03144  (EXPT01692)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIINot Available
CAS numberNot Available
WeightAverage: 190.2004
Monoisotopic: 190.106590334
Chemical FormulaC6H14N4O3
InChI KeyFQWRAVYMZULPNK-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-(1-hydroxycarbamimidamido)pentanoic acid
SMILES
N[C@@H](CCCNC(=N)NO)C(O)=O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Nitric oxide synthase, endothelialProteinunknownNot AvailableHumanP29474 details
Nitric oxide synthase oxygenaseProteinunknownNot AvailableBacillus subtilis (strain 168)O34453 details
Nitric oxide synthase, inducibleProteinunknownNot AvailableHumanP35228 details
Arginase-1ProteinunknownNot AvailableHumanP05089 details
Nitric oxide synthase, brainProteinunknownNot AvailableHumanP29475 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentArginine and derivatives
Alternative ParentsL-alpha-amino acids / N-hydroxyguanidines / Fatty acids and conjugates / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Carboximidamides / Organopnictogen compounds / Organic oxides / Monoalkylamines
SubstituentsArginine or derivatives / Alpha-amino acid / L-alpha-amino acid / Fatty acid / N-hydroxyguanidine / Guanidine / Amino acid / Carboxylic acid / Monocarboxylic acid or derivatives / Carboximidamide
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsN(omega)-hydroxy-L-arginine, N(5)-[(hydroxyamino)(imino)methyl]ornithine (CHEBI:43088 )

Targets

Kind
Protein
Organism
Human
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)-induced angiogenesis in coronary vessels and promotes blood clotting through the activation of platelets.Isoform eNOS13C: Lacks eNOS activity, dominant-negative form that may down-regulate eNOS activity by ...
Gene Name:
NOS3
Uniprot ID:
P29474
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. [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 ]
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
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. [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 ]
Kind
Protein
Organism
Human
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 and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2. As component of the iNOS-S100A8/9 transnitrosylase complex involved in the selective inflammatory stimulus-dependent S-n...
Gene Name:
NOS2
Uniprot ID:
P35228
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. [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 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Manganese ion binding
Specific Function:
Not Available
Gene Name:
ARG1
Uniprot ID:
P05089
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 ]
Kind
Protein
Organism
Human
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. Probably has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such SRR.
Gene Name:
NOS1
Uniprot ID:
P29475
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. [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 11, 2017 20:45