vasopressin   Click here for help

GtoPdb Ligand ID: 2168

Abbreviated name: AVP
Synonyms: ADH | antidiuretic hormone | arginine vasopressin | argipressin
Approved drug
vasopressin is an approved drug (FDA (date of approval not specified))
Compound class: Endogenous peptide in human, mouse or rat
Comment: The approved drug is administered as an injection, as indicated by the INN.

As with all large peptide molecules, there is some ambiguity in representations of the stereochemistry of vasopressin, therefore the chemical structure shown here may differ slightly from that shown on other resouces linked to from the table above.
Species: Human, Mouse, Rat
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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

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View more information in the IUPHAR Pharmacology Education Project: vasopressin

vasopressin is commercially available from our sponsors

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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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 NC(=O)CC1NC(=O)C(CCC(=O)N)NC(=O)C(Cc2ccccc2)NC(=O)C(Cc2ccc(cc2)O)NC(=O)C(CSSCC(NC1=O)C(=O)N1CCCC1C(=O)NC(C(=O)NCC(=O)N)CCCN=C(N)N)N
Isomeric SMILES NC(=O)C[C@@H]1NC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@H](CSSC[C@H](NC1=O)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)NCC(=O)N)CCCN=C(N)N)N
InChI InChI=1S/C46H65N15O12S2/c47-27-22-74-75-23-33(45(73)61-17-5-9-34(61)44(72)56-28(8-4-16-53-46(51)52)39(67)54-21-37(50)65)60-43(71)32(20-36(49)64)59-40(68)29(14-15-35(48)63)55-41(69)31(18-24-6-2-1-3-7-24)58-42(70)30(57-38(27)66)19-25-10-12-26(62)13-11-25/h1-3,6-7,10-13,27-34,62H,4-5,8-9,14-23,47H2,(H2,48,63)(H2,49,64)(H2,50,65)(H,54,67)(H,55,69)(H,56,72)(H,57,66)(H,58,70)(H,59,68)(H,60,71)(H4,51,52,53)/t27-,28-,29-,30-,31-,32-,33-,34-/m0/s1
InChI Key KBZOIRJILGZLEJ-LGYYRGKSSA-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/)
Natural/Endogenous Targets
Target
OT receptor
V1A receptor
V1B receptor
V2 receptor
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
OATP3A1
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
V1B receptor Ligand is endogenous in the given species Rn Agonist Full agonist 9.9 pKi - 15
⤷ pKi 9.9 [15]
V1B receptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Full agonist 9.0 – 9.5 pKi - 1,3,8-9,12,15,17-18,20-21
⤷ pKi 9.0 – 9.5 [1,3,8-9,12,15,17-18,20-21]
V1A receptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Full agonist 8.5 – 9.3 pKi - 1,3,7-8,12,14-15,17-21
⤷ pKi 8.5 – 9.3 [1,3,7-8,12,14-15,17-21]
V2 receptor Primary target of this compound Ligand is endogenous in the given species Hs Agonist Full agonist 7.9 – 9.1 pKi - 1,3-4,8,12,15-18,20-21
⤷ pKi 7.9 – 9.1 [1,3-4,8,12,15-18,20-21]
V1A receptor Ligand is endogenous in the given species Rn Agonist Full agonist 8.4 pKi - 4
⤷ pKi 8.4 [4]
OT receptor Ligand is endogenous in the given species Hs Agonist Partial agonist 7.3 – 9.3 pKi - 1-5,8-10
⤷ pKi 7.3 – 9.3 [1-5,8-10]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Potency order of endogenous ligands at V1A receptor vasopressin (AVP, P01185) > oxytocin (OXT, P01178) 1,3,7,12,15,18-19
Potency order of endogenous ligands at V1B receptor vasopressin (AVP, P01185) > oxytocin (OXT, P01178) 1,3,8-9,12,15,18,20
Potency order of endogenous ligands at V2 receptor vasopressin (AVP, P01185) > oxytocin (OXT, P01178) 1,3-4,13,16,18,21
Potency order of endogenous ligands at OT receptor oxytocin (OXT, P01178) > vasopressin (AVP, P01185) 1,4-6,9-11
Targets where the ligand is described in the comment field
Target Comment
Leucyl-cysteinyl aminopeptidase This enzyme hydrolyses vasopressin (AVP, P01185), oxytocin (OXT, P01178), kallidin (KNG1, P01042), [Met]enkephalin (PENK, P01210), dynorphin A (PDYN, P01213).
Ligand mentioned in the following text fields
Vasopressin and oxytocin receptors overview