histamine   Click here for help

GtoPdb Ligand ID: 1204

PDB Ligand Immunopharmacology Ligand
Compound class: Metabolite
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].
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2D Structure
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Physico-chemical Properties
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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
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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