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

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: vasopressin

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.

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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
Classification Click here for help
Compound class Endogenous peptide in human, mouse or rat
Ligand families/groups Neuropeptides
Approved drug? Yes (FDA (date of approval not specified))
IUPAC Name Click here for help
(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-13-(phenylmethyl)1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]pyrrolidine-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
2144 vasopressin injection
Synonyms Click here for help
ADH | antidiuretic hormone | arginine vasopressin | argipressin
Gene/Precursor Click here for help
Gene symbol Gene name Species Precursor protein name Synonyms
AVP arginine vasopressin Human prepro-AVP-NP II (prepro-arginine-vasopressin-neurophysin II) ADH, antidiuretic hormone, ARVP, diabetes insipidus, neurohypophyseal, neurophysin II
Avp arginine vasopressin Mouse prepro-AVP-NP II (prepro-arginine-vasopressin-neurophysin II) Vp, Vsp
Avp arginine vasopressin Rat prepro-AVP-NP II (prepro-arginine-vasopressin-neurophysin II) Arginine vasopressin (Diabetes insipidus), arginine vasopressin (Diabetes insipidus) same as Di (conflicting physical mapping), arginine vasopressin (Diabetes insipidus), same as Di (conflicting physical mapping), Arginine vasopressin (Diabetes insipidus) same as Di (conflicting physical mapping), AVP-NPII, DI, prepropressophysin, preprovasopressin-neurophysin, Vas, vasopressin-neurophysin 2-copeptin, vasopressin-neurophysin prepropeptide
Database Links Click here for help
Specialist databases
GPCRdb Ligand vasopressin
Other databases
CAS Registry No. 50-56-6
CATH/Gene3D 2.60.9.10
ChEBI CHEBI:34543
ChEMBL Ligand CHEMBL373742
DrugBank Ligand DB00067
DrugCentral Ligand 2810
Ensembl Gene ENSG00000101200 (Hs), ENSMUSG00000037727 (Mm), ENSRNOG00000021229 (Rn)
GtoPdb PubChem SID 135651625
Human Protein Atlas ENSG00000101200 (Hs)
PubChem CID 644077
Search Google for chemical match using the InChIKey KBZOIRJILGZLEJ-LGYYRGKSSA-N
Search Google for chemicals with the same backbone KBZOIRJILGZLEJ
Search PubMed clinical trials vasopressin injection
Search PubMed titles vasopressin injection
Search PubMed titles/abstracts vasopressin injection
UniChem Compound Search for chemical match using the InChIKey KBZOIRJILGZLEJ-LGYYRGKSSA-N
UniChem Connectivity Search for chemical match using the InChIKey KBZOIRJILGZLEJ-LGYYRGKSSA-N
UniProtKB P01186 (Rn), P35455 (Mm), P01185 (Hs)
Wikipedia Vasopressin