oxytocin   Click here for help

GtoPdb Ligand ID: 2174

Abbreviated name: OT
Synonyms: Otx | Pitocin® | Syntocinon®
Approved drug
oxytocin is an approved drug (FDA (1980))
Compound class: Endogenous peptide in human, mouse or rat
Comment: Endogenous oxytocin is a hormone and neuropeptide, which plays a role in social bonding, sexual reproduction and is required during and after childbirth. Purified oxytocin is used clinically.
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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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 CCC(C1NC(=O)C(Cc2ccc(cc2)O)NC(=O)C(N)CSSCC(NC(=O)C(NC(=O)C(NC1=O)CCC(=O)N)CC(=O)N)C(=O)N1CCCC1C(=O)NC(C(=O)NCC(=O)N)CC(C)C)C
Isomeric SMILES CC[C@@H]([C@@H]1NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@@H](N)CSSC[C@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)CCC(=O)N)CC(=O)N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)NCC(=O)N)CC(C)C)C
InChI InChI=1S/C43H66N12O12S2/c1-5-22(4)35-42(66)49-26(12-13-32(45)57)38(62)51-29(17-33(46)58)39(63)53-30(20-69-68-19-25(44)36(60)50-28(40(64)54-35)16-23-8-10-24(56)11-9-23)43(67)55-14-6-7-31(55)41(65)52-27(15-21(2)3)37(61)48-18-34(47)59/h8-11,21-22,25-31,35,56H,5-7,12-20,44H2,1-4H3,(H2,45,57)(H2,46,58)(H2,47,59)(H,48,61)(H,49,66)(H,50,60)(H,51,62)(H,52,65)(H,53,63)(H,54,64)/t22-,25-,26-,27-,28-,29-,30-,31-,35-/m0/s1
InChI Key XNOPRXBHLZRZKH-DSZYJQQASA-N
Classification Click here for help
Compound class Endogenous peptide in human, mouse or rat
Ligand families/groups Neuropeptides
Approved drug? Yes (FDA (1980))
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
(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-[(2S)-butan-2-yl]-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]pyrrolidine-2-carboxamide
International Nonproprietary Names Click here for help
INN number INN
1480 oxytocin
Synonyms Click here for help
Otx | Pitocin® | Syntocinon®
Gene/Precursor Click here for help
Gene symbol Gene name Species Precursor protein name Synonyms
OXT oxytocin/neurophysin I prepropeptide Human prepro-OXT-NP I (prepro-oxytocin-neurophysin I) neurophysin I, OT, oxytocin, prepro- (neurophysin I), oxytocin, prepropeptide
Oxt oxytocin Mouse prepro-OXT-NP I (prepro-oxytocin-neurophysin I) Oxy
Oxt oxytocin/neurophysin I prepropeptide Rat prepro-OXT-NP I (prepro-oxytocin-neurophysin I) OT-NPI, oxcytocin, oxytocin, Oxytocin/neurophysin, oxytocin-neurophysin 1, oxytocin/neurophysin 1 prepropeptide, oxytocin/neurophysin (Oxt) gene, complete gene, complete cds, oxytocin, prepropeptide, Rat oxytocin/neurophysin (Oxt) gene complete gene complete cds
Database Links Click here for help
Specialist databases
GPCRdb Ligand oxytocin
Other databases
CAS Registry No. 50-56-6
CATH/Gene3D 2.60.9.10
ChEBI CHEBI:7872
ChEMBL Ligand CHEMBL395429
DrugBank Ligand DB00107
DrugCentral Ligand 2042
Ensembl Gene ENSRNOG00000021225 (Rn), ENSMUSG00000027301 (Mm), ENSG00000101405 (Hs)
GtoPdb PubChem SID 135651848
Human Protein Atlas ENSG00000101405 (Hs)
PubChem CID 439302
Search Google for chemical match using the InChIKey XNOPRXBHLZRZKH-DSZYJQQASA-N
Search Google for chemicals with the same backbone XNOPRXBHLZRZKH
Search PubMed clinical trials oxytocin
Search PubMed titles oxytocin
Search PubMed titles/abstracts oxytocin
UniChem Compound Search for chemical match using the InChIKey XNOPRXBHLZRZKH-DSZYJQQASA-N
UniChem Connectivity Search for chemical match using the InChIKey XNOPRXBHLZRZKH-DSZYJQQASA-N
UniProtKB P01178 (Hs), P01179 (Rn), P35454 (Mm)
Wikipedia Oxytocin

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Tocris
Oxytocin (links to external site)
Cat. No. 1910