histamine   Click here for help

GtoPdb Ligand ID: 1204

PDB Ligand Immunopharmacology Ligand
Compound class: Metabolite or derivative
Comment: Histamine is a potent pro-inflammatory mediator that is principally released from mast cells. It is also involved in regulating physiological function in the gut, and acts as a neurotransmitter.
Histamine activates carbonic anhydrases, and is most potent at the CA5A and CA1 isoforms (KA values 10 and 2100 nM respectively) [21].
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: histamine

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 2
Hydrogen bond donors 2
Rotatable bonds 2
Topological polar surface area 54.7
Molecular weight 111.08
XLogP -0.75
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 NCCc1cnc[nH]1
Isomeric SMILES NCCc1cnc[nH]1
InChI InChI=1S/C5H9N3/c6-2-1-5-3-7-4-8-5/h3-4H,1-2,6H2,(H,7,8)
InChI Key NTYJJOPFIAHURM-UHFFFAOYSA-N
Natural/Endogenous Targets
Target
H1 receptor
H2 receptor
H3 receptor
H4 receptor
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
Histidine decarboxylase
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
Vesicular monoamine transporter 1 6
Vesicular monoamine transporter 2 6
Organic cation transporter 2 8
Plasma membrane monoamine transporter 5,23
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
H3 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 7.8 – 8.3 pKi - 4,9-10,12,14,24
⤷ pKi 7.8 – 8.3 [4,9-10,12,14,24]
H4 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 7.8 – 8.3 pKi - 7,11-13,17,22,26
⤷ pKi 7.8 – 8.3 [7,11-13,17,22,26]
H3 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 7.2 – 7.9 pKi - 10,14,16
⤷ pKi 7.2 – 7.9 [10,14,16]
H3 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 7.1 – 7.8 pKi - 3,19
⤷ pKi 7.1 – 7.8 [3,19]
H4 receptor Ligand is endogenous in the given species Mm Agonist Full agonist 7.4 pKi - 13
⤷ pKi 7.4 [13]
H4 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 7.2 pKi - 13
⤷ pKi 7.2 [13]
H1 receptor Ligand is endogenous in the given species Hs Agonist Full agonist 4.7 – 5.9 pKi - 2,15,18,20,25
⤷ pKi 4.7 – 5.9 [2,15,18,20,25]
H2 receptor Ligand is endogenous in the given species Rn Agonist Full agonist 3.8 pKi - 1
⤷ pKi 3.8 [1]
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
carbonic anhydrase 1 Hs Activator Activation - - - 21
⤷ KA of 2100 nM. [21]
carbonic anhydrase 7 Hs Activator Activation - - - 21
⤷ KA 37500 nM. [21]
carbonic anhydrase 5A Hs Activator Activation - - - 21
⤷ KA 10 nM. [21]
Ligand mentioned in the following text fields
Histamine receptors overview
Voltage-gated proton channel (Hv1) comments