L-N(Omega)-Nitroarginine-2,4-L-Diaminobutyric Amide

Identification

Name
L-N(Omega)-Nitroarginine-2,4-L-Diaminobutyric Amide
Accession Number
DB01821  (EXPT01252)
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: 318.3329
Monoisotopic: 318.176401232
Chemical Formula
C10H22N8O4
InChI Key
KUZKVXUOMSVPOA-BQBZGAKWSA-N
InChI
InChI=1S/C10H22N8O4/c11-4-3-7(8(13)19)16-9(20)6(12)2-1-5-15-10(14)17-18(21)22/h6-7H,1-5,11-12H2,(H2,13,19)(H,16,20)(H3,14,15,17)/t6-,7-/m0/s1
IUPAC Name
(2S)-2-amino-N-[(1S)-3-amino-1-(C-hydroxycarbonimidoyl)propyl]-5-(1-nitrocarbamimidamido)pentanimidic acid
SMILES
[H][[email protected]](N)(CCCNC(=N)NN(=O)=O)C(O)=N[[email protected]@]([H])(CCN)C(O)=N

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
656910
PubChem Substance
46509184
ChemSpider
571159
BindingDB
22030
ChEMBL
CHEMBL44833
HET
DP1
PDB Entries
1p6h / 1p6k / 1p6l / 1q2o / 1zzu

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 Solubility0.249 mg/mLALOGPS
logP-1.2ALOGPS
logP-7.1ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)-1.3ChemAxon
pKa (Strongest Basic)12.9ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area222.44 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity99.55 m3·mol-1ChemAxon
Polarizability31.54 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9032
Blood Brain Barrier+0.6975
Caco-2 permeable-0.6424
P-glycoprotein substrateNon-substrate0.5199
P-glycoprotein inhibitor INon-inhibitor0.8885
P-glycoprotein inhibitor IINon-inhibitor0.943
Renal organic cation transporterNon-inhibitor0.8714
CYP450 2C9 substrateNon-substrate0.8088
CYP450 2D6 substrateNon-substrate0.7956
CYP450 3A4 substrateNon-substrate0.6677
CYP450 1A2 substrateNon-inhibitor0.8585
CYP450 2C9 inhibitorNon-inhibitor0.8358
CYP450 2D6 inhibitorNon-inhibitor0.9102
CYP450 2C19 inhibitorNon-inhibitor0.8036
CYP450 3A4 inhibitorNon-inhibitor0.8751
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9723
Ames testAMES toxic0.8454
CarcinogenicityNon-carcinogens0.7712
BiodegradationReady biodegradable0.8824
Rat acute toxicity2.5862 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8737
hERG inhibition (predictor II)Non-inhibitor0.8449
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 dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Nitroguanidines / N-acyl amines / Nitramines / Secondary carboxylic acid amides / Primary carboxylic acid amides / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Organopnictogen compounds
show 5 more
Substituents
Alpha-dipeptide / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / Nitroguanidine / Fatty amide / N-acyl-amine / Fatty acyl / Nitramine
show 23 more
Molecular Framework
Aliphatic acyclic 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 14:49