nitroglycerin   Click here for help

GtoPdb Ligand ID: 7053

Synonyms: glyceryl trinitrate | Glytrin® | Minitran® | Rectogesic®
Approved drug PDB Ligand
nitroglycerin is an approved drug (FDA (no history prior to 1981))
Compound class: Synthetic organic
Comment: Nitroglycerin acts as a vasodilator.
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View more information in the IUPHAR Pharmacology Education Project: nitroglycerin

2D Structure
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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.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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.

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Hydrogen bond acceptors 0
Hydrogen bond donors 0
Rotatable bonds 8
Topological polar surface area 157.11
Molecular weight 227
XLogP 0.98
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES [O-][N+](=O)OC(CO[N+](=O)[O-])CO[N+](=O)[O-]
Isomeric SMILES [O-][N+](=O)OC(CO[N+](=O)[O-])CO[N+](=O)[O-]
InChI InChI=1S/C3H5N3O9/c7-4(8)13-1-3(15-6(11)12)2-14-5(9)10/h3H,1-2H2
InChI Key SNIOPGDIGTZGOP-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (no history prior to 1981))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
1,3-dinitrooxypropan-2-yl nitrate
Synonyms Click here for help
glyceryl trinitrate | Glytrin® | Minitran® | Rectogesic®
Database Links Click here for help
CAS Registry No. 55-63-0 (source: Scifinder)
ChEMBL Ligand CHEMBL730
DrugBank Ligand DB00727
DrugCentral Ligand 1952
GtoPdb PubChem SID 178103632
PubChem CID 4510
RCSB PDB Ligand TNG
Search Google for chemical match using the InChIKey SNIOPGDIGTZGOP-UHFFFAOYSA-N
Search Google for chemicals with the same backbone SNIOPGDIGTZGOP
UniChem Compound Search for chemical match using the InChIKey SNIOPGDIGTZGOP-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey SNIOPGDIGTZGOP-UHFFFAOYSA-N
Wikipedia Nitroglycerin