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Identification
NameN-{(3R,4S)-4-[(6-amino-4-methylpyridin-2-yl)methyl]pyrrolidin-3-yl}-N'-(3-chlorobenzyl)ethane-1,2-diamine
Accession NumberDB08019
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: 373.923
Monoisotopic: 373.203323628
Chemical FormulaC20H28ClN5
InChI KeyVWCMAGONQJHIJZ-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][C@]1(CC2=NC(N)=CC(C)=C2)CNC[C@]1([H])NCCNCC1=CC(Cl)=CC=C1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Nitric oxide synthase, brainProteinunknownNot AvailableHumanP29475 details
Nitric oxide synthase, endothelialProteinunknownNot AvailableHumanP29474 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 EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylmethylamines
Direct ParentPhenylmethylamines
Alternative Parents
Substituents
  • Phenylmethylamine
  • Benzylamine
  • Methylpyridine
  • Aralkylamine
  • Halobenzene
  • Chlorobenzene
  • Aminopyridine
  • Imidolactam
  • Pyridine
  • Primary aromatic amine
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Pyrrolidine
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic 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 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. 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)-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. 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 September 15, 2010 15:27 / Updated on August 17, 2016 12:24