thiamine   Click here for help

GtoPdb Ligand ID: 4629

Synonyms: vitamin B1
PDB Ligand
Compound class: Metabolite or derivative
Comment: Approved as a nutraceutical by the FDA as thiamine hydrochloride in 1972, no prior history available.
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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.

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View interactive charts of activity data across species
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 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.

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Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 4
Topological polar surface area 104.15
Molecular weight 265.11
XLogP 0.38
No. Lipinski's rules broken 0
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.

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Canonical SMILES OCCc1sc[n+](c1C)Cc1cnc(nc1N)C
Isomeric SMILES OCCc1sc[n+](c1C)Cc1cnc(nc1N)C
InChI InChI=1S/C12H17N4OS/c1-8-11(3-4-17)18-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7,17H,3-4,6H2,1-2H3,(H2,13,14,15)/q+1
InChI Key JZRWCGZRTZMZEH-UHFFFAOYSA-N
Classification Click here for help
Compound class Metabolite or derivative
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
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium
International Nonproprietary Names Click here for help
INN number INN
432 thiamine
Synonyms Click here for help
vitamin B1
Database Links Click here for help
BitterDB Ligand 68
CAS Registry No. 59-43-8 (source: Scifinder)
ChEMBL Ligand CHEMBL1547
DrugBank Ligand DB00152
DrugCentral Ligand 2832
GtoPdb PubChem SID 178101347
PubChem CID 1130
RCSB PDB Ligand VIB
Search Google for chemical match using the InChIKey JZRWCGZRTZMZEH-UHFFFAOYSA-N
Search Google for chemicals with the same backbone JZRWCGZRTZMZEH
Search PubMed clinical trials thiamine
Search PubMed titles thiamine
Search PubMed titles/abstracts thiamine
UniChem Compound Search for chemical match using the InChIKey JZRWCGZRTZMZEH-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey JZRWCGZRTZMZEH-UHFFFAOYSA-N
Wikipedia Thiamine