L-N(Omega)-Nitroarginine-(4r)-Amino-L-Proline Amide

Identification

Name
L-N(Omega)-Nitroarginine-(4r)-Amino-L-Proline Amide
Accession Number
DB02077  (EXPT01254)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 330.3436
Monoisotopic: 330.176401232
Chemical Formula
C11H22N8O4
InChI Key
IUFRDGFKAVLPFZ-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[[email protected]@H](CCCNC(=N)N[N+]([O-])=O)C(=O)N[[email protected]]1CN[[email protected]@H](C1)C(N)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNitric oxide synthase, endothelialNot AvailableHuman
UNitric oxide synthase, brainNot AvailableHuman
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
656912
PubChem Substance
46507698
ChemSpider
571161
BindingDB
50138976
ChEMBL
CHEMBL228077
HET
DP9
PDB Entries
1p6j / 1p6n / 1zzq / 1zzr / 1zzs / 1zzt

Clinical Trials

Clinical Trials
Not Available

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 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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

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 proline and derivatives. These are compounds containing proline or a derivative thereof resulting from reaction of proline 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
Proline and derivatives
Alternative Parents
Alpha amino acid amides / Pyrrolidinecarboxamides / Nitroguanidines / N-acyl amines / Nitramines / Secondary carboxylic acid amides / Primary carboxylic acid amides / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Carboximidamides
show 7 more
Substituents
Proline or derivatives / Alpha-amino acid amide / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine-2-carboxamide / Nitroguanidine / Fatty amide / N-acyl-amine / Fatty acyl / Nitramine / Pyrrolidine
show 26 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not 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)-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. [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. 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. [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 December 01, 2017 14:52