NAV

N-{(3S,4S)-4-[(6-AMINO-4-METHYLPYRIDIN-2-YL)METHYL]PYRROLIDIN-3-YL}-N'-(4-CHLOROBENZYL)ETHANE-1,2-DIAMINE

Identification

Generic Name
N-{(3S,4S)-4-[(6-AMINO-4-METHYLPYRIDIN-2-YL)METHYL]PYRROLIDIN-3-YL}-N'-(4-CHLOROBENZYL)ETHANE-1,2-DIAMINE
DrugBank Accession Number
DB08018
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 373.923
Monoisotopic: 373.203323628
Chemical Formula
C20H28ClN5
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNitric oxide synthase, brainNot AvailableHumans
UNitric oxide synthase, endothelialNot AvailableHumans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
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
Amine / Aminopyridine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzylamine / Chlorobenzene / Halobenzene
show 16 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
JDRSQGJWTVRNGM-QFBILLFUSA-N
InChI
InChI=1S/C20H28ClN5/c1-14-8-18(26-20(22)9-14)10-16-12-24-13-19(16)25-7-6-23-11-15-2-4-17(21)5-3-15/h2-5,8-9,16,19,23-25H,6-7,10-13H2,1H3,(H2,22,26)/t16-,19+/m0/s1
IUPAC Name
6-{[(3S,4S)-4-[(2-{[(4-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=C(Cl)C=C1

References

General References
Not Available
PubChem Compound
24798097
PubChem Substance
99444489
ChemSpider
24697467
BindingDB
29234
ChEMBL
CHEMBL474637
ZINC
ZINC000039036155
PDBe Ligand
JI3
PDB Entries
3b3o / 3dqs

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.00739 mg/mLALOGPS
logP1.44ALOGPS
logP2.35Chemaxon
logS-4.7ALOGPS
pKa (Strongest Basic)10.18Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area75 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity108.71 m3·mol-1Chemaxon
Polarizability42.49 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/MSsplash10-00di-0009000000-776e25fe73797571e793
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-a1468b8e02d21d6b718a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9004000000-37bb5d5633bf66f7ad62
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-067i-0596000000-3b5bbf971d7fd223754b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9422000000-4cfd7bf5ab6159d415f8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0hr0-1972000000-a07b28bb2f0fc90e31a9
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-187.1122
predicted
DeepCCS 1.0 (2019)
[M+H]+189.50775
predicted
DeepCCS 1.0 (2019)
[M+Na]+195.4203
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Nitric oxide synthase, brain
Kind
Protein
Organism
Humans
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. [Article]
Details2. Nitric oxide synthase, endothelial
Kind
Protein
Organism
Humans
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. [Article]

Drug created at September 15, 2010 21:27 / Updated at June 12, 2020 16:52