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Identification
NameL-N(Omega)-Nitroarginine-(4r)-Amino-L-Proline Amide
Accession NumberDB02077  (EXPT01254)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers 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
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 330.3436
Monoisotopic: 330.176401232
Chemical FormulaC11H22N8O4
InChI KeyIUFRDGFKAVLPFZ-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-(1-nitrocarbamimidamido)pentanamido]pyrrolidine-2-carboxamide
SMILES
N[C@@H](CCCNC(=N)N[N+]([O-])=O)C(=O)N[[email protected]]1CN[C@@H](C1)C(N)=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, 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
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot 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
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8817
Blood Brain Barrier+0.7548
Caco-2 permeable-0.6381
P-glycoprotein substrateSubstrate0.5934
P-glycoprotein inhibitor INon-inhibitor0.9314
P-glycoprotein inhibitor IINon-inhibitor0.9417
Renal organic cation transporterNon-inhibitor0.838
CYP450 2C9 substrateNon-substrate0.8241
CYP450 2D6 substrateNon-substrate0.8017
CYP450 3A4 substrateNon-substrate0.6534
CYP450 1A2 substrateNon-inhibitor0.795
CYP450 2C9 inhibitorNon-inhibitor0.8259
CYP450 2D6 inhibitorNon-inhibitor0.8964
CYP450 2C19 inhibitorNon-inhibitor0.7849
CYP450 3A4 inhibitorNon-inhibitor0.8707
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9694
Ames testAMES toxic0.7612
CarcinogenicityNon-carcinogens0.866
BiodegradationReady biodegradable0.8775
Rat acute toxicity2.5363 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8174
hERG inhibition (predictor II)Non-inhibitor0.7411
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.297 mg/mLALOGPS
logP-2ALOGPS
logP-3.5ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)10.06ChemAxon
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.97 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity90.57 m3·mol-1ChemAxon
Polarizability32.54 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine carboxylic acid or derivatives
  • Fatty acyl
  • N-acyl-amine
  • Fatty amide
  • Pyrrolidine
  • Nitramine
  • Organic nitro compound
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Guanidine
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Allyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Secondary amine
  • Secondary aliphatic amine
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organic salt
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Imine
  • Carbonyl group
  • Amine
  • Organic zwitterion
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available

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
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23