N-{(4s)-4-Amino-5-[(2-Aminoethyl)Amino]Pentyl}-N'-Nitroguanidine

Identification

Name
N-{(4s)-4-Amino-5-[(2-Aminoethyl)Amino]Pentyl}-N'-Nitroguanidine
Accession Number
DB02027  (EXPT01253)
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: 247.298
Monoisotopic: 247.175672951
Chemical Formula
C8H21N7O2
InChI Key
RMSWBHUVFNFNIZ-ZETCQYMHSA-N
InChI
InChI=1S/C8H21N7O2/c9-3-5-12-6-7(10)2-1-4-13-8(11)14-15(16)17/h7,12H,1-6,9-10H2,(H3,11,13,14)/t7-/m0/s1
IUPAC Name
3-[(4S)-4-amino-5-[(2-aminoethyl)amino]pentyl]-1-nitroguanidine
SMILES
NCCNC[[email protected]@H](N)CCCNC(=N)N[N+]([O-])=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
656911
PubChem Substance
46504827
ChemSpider
571160
BindingDB
21960
ChEMBL
CHEMBL227937
HET
DP3
PDB Entries
1p6i / 1p6m

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 Solubility0.338 mg/mLALOGPS
logP-1.4ALOGPS
logP-2.4ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)10.3ChemAxon
pKa (Strongest Basic)9.72ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area157.8 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity75.42 m3·mol-1ChemAxon
Polarizability25.98 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7614
Blood Brain Barrier+0.7658
Caco-2 permeable-0.5863
P-glycoprotein substrateSubstrate0.5366
P-glycoprotein inhibitor INon-inhibitor0.9295
P-glycoprotein inhibitor IINon-inhibitor0.9405
Renal organic cation transporterNon-inhibitor0.7153
CYP450 2C9 substrateNon-substrate0.8917
CYP450 2D6 substrateNon-substrate0.7677
CYP450 3A4 substrateNon-substrate0.7287
CYP450 1A2 substrateNon-inhibitor0.838
CYP450 2C9 inhibitorNon-inhibitor0.8482
CYP450 2D6 inhibitorNon-inhibitor0.9005
CYP450 2C19 inhibitorNon-inhibitor0.8375
CYP450 3A4 inhibitorNon-inhibitor0.9418
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9763
Ames testAMES toxic0.858
CarcinogenicityNon-carcinogens0.6753
BiodegradationNot ready biodegradable0.586
Rat acute toxicity2.4278 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.8309
hERG inhibition (predictor II)Non-inhibitor0.8151
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 nitroguanidines. These are organonitrogen compounds containing a nitro group, which is N-linked to a guanidine.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Guanidines
Direct Parent
Nitroguanidines
Alternative Parents
Nitramines / Propargyl-type 1,3-dipolar organic compounds / Dialkylamines / Carboximidamides / Organopnictogen compounds / Organic zwitterions / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
Substituents
Nitroguanidine / Nitramine / Organic nitro compound / Secondary aliphatic amine / Secondary amine / Carboximidamide / Allyl-type 1,3-dipolar organic compound / Propargyl-type 1,3-dipolar organic compound / Organic 1,3-dipolar compound / Organic zwitterion
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 14:52