N-{(3R,4S)-4-[(6-amino-4-methylpyridin-2-yl)methyl]pyrrolidin-3-yl}-N'-(3-chlorobenzyl)ethane-1,2-diamine

Identification

Name
N-{(3R,4S)-4-[(6-amino-4-methylpyridin-2-yl)methyl]pyrrolidin-3-yl}-N'-(3-chlorobenzyl)ethane-1,2-diamine
Accession Number
DB08019
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: 373.923
Monoisotopic: 373.203323628
Chemical Formula
C20H28ClN5
InChI Key
VWCMAGONQJHIJZ-LPHOPBHVSA-N
InChI
InChI=1S/C20H28ClN5/c1-14-7-18(26-20(22)8-14)10-16-12-24-13-19(16)25-6-5-23-11-15-3-2-4-17(21)9-15/h2-4,7-9,16,19,23-25H,5-6,10-13H2,1H3,(H2,22,26)/t16-,19-/m0/s1
IUPAC Name
6-{[(3S,4R)-4-[(2-{[(3-chlorophenyl)methyl]amino}ethyl)amino]pyrrolidin-3-yl]methyl}-4-methylpyridin-2-amine
SMILES
[H][[email protected]]1(CC2=NC(N)=CC(C)=C2)CNC[[email protected]]1([H])NCCNCC1=CC(Cl)=CC=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNitric oxide synthase, brainNot AvailableHuman
UNitric oxide synthase, endothelialNot 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
25021186
PubChem Substance
99444490
ChemSpider
24721145
BindingDB
29235
ChEMBL
CHEMBL526688
HET
JI7
PDB Entries
3b3p / 3dqt

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 Solubility0.00759 mg/mLALOGPS
logP1.44ALOGPS
logP2.35ChemAxon
logS-4.7ALOGPS
pKa (Strongest Basic)10.19ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area75 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity108.71 m3·mol-1ChemAxon
Polarizability42.89 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9597
Blood Brain Barrier+0.7937
Caco-2 permeable-0.5898
P-glycoprotein substrateSubstrate0.7817
P-glycoprotein inhibitor INon-inhibitor0.8462
P-glycoprotein inhibitor IINon-inhibitor0.8188
Renal organic cation transporterInhibitor0.5842
CYP450 2C9 substrateNon-substrate0.8486
CYP450 2D6 substrateNon-substrate0.7762
CYP450 3A4 substrateNon-substrate0.5661
CYP450 1A2 substrateInhibitor0.5754
CYP450 2C9 inhibitorNon-inhibitor0.8085
CYP450 2D6 inhibitorInhibitor0.5337
CYP450 2C19 inhibitorNon-inhibitor0.8442
CYP450 3A4 inhibitorNon-inhibitor0.7587
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8926
Ames testNon AMES toxic0.6711
CarcinogenicityNon-carcinogens0.894
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7365 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5099
hERG inhibition (predictor II)Inhibitor0.7484
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 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 phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylmethylamines
Direct Parent
Phenylmethylamines
Alternative Parents
Benzylamines / Methylpyridines / Chlorobenzenes / Aralkylamines / Aminopyridines and derivatives / Imidolactams / Aryl chlorides / Pyrrolidines / Heteroaromatic compounds / Dialkylamines
show 5 more
Substituents
Benzylamine / Phenylmethylamine / Aminopyridine / Chlorobenzene / Halobenzene / Aralkylamine / Methylpyridine / Imidolactam / Pyridine / Aryl halide
show 16 more
Molecular Framework
Aromatic 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 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. 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 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. 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 September 15, 2010 15:27 / Updated on December 01, 2017 15:59