nortriptyline   Click here for help

GtoPdb Ligand ID: 2404

Synonyms: Aventyl® | nortriptyline hydrochloride | Pamelor®
Approved drug PDB Ligand
nortriptyline is an approved drug (FDA (1964))
Compound class: Synthetic organic
Comment: Nortriptyline is a second-generation tricyclic antidepressant (TCA).
Click here for help

Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

✖

View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: nortriptyline

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 12.03
Molecular weight 263.17
XLogP 4.69
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES CNCCC=C1c2ccccc2CCc2c1cccc2
Isomeric SMILES CNCCC=C1c2ccccc2CCc2c1cccc2
InChI InChI=1S/C19H21N/c1-20-14-6-11-19-17-9-4-2-7-15(17)12-13-16-8-3-5-10-18(16)19/h2-5,7-11,20H,6,12-14H2,1H3
InChI Key PHVGLTMQBUFIQQ-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1964))
IUPAC Name Click here for help
methyl({3-[(2E)-tricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-2-ylidene]propyl})amine
International Nonproprietary Names Click here for help
INN number INN
1328 nortriptyline
Synonyms Click here for help
Aventyl® | nortriptyline hydrochloride | Pamelor®
Database Links Click here for help
BindingDB Ligand 50020710
CAS Registry No. 72-69-5 (source: DrugBank)
ChEBI CHEBI:7640
ChEMBL Ligand CHEMBL445
DrugBank Ligand DB00540
DrugCentral Ligand 1971
GtoPdb PubChem SID 135650736
PubChem CID 4543
RCSB PDB Ligand 21B
Search Google for chemical match using the InChIKey PHVGLTMQBUFIQQ-UHFFFAOYSA-N
Search Google for chemicals with the same backbone PHVGLTMQBUFIQQ
Search PubMed clinical trials nortriptyline
Search PubMed titles nortriptyline
Search PubMed titles/abstracts nortriptyline
UniChem Compound Search for chemical match using the InChIKey PHVGLTMQBUFIQQ-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey PHVGLTMQBUFIQQ-UHFFFAOYSA-N
Wikipedia Nortriptyline