oxytocin   

GtoPdb Ligand ID: 2174

Abbreviated name: OT
Synonyms: Otx | Pitocin® | Syntocinon®
oxytocin is an approved drug (FDA (1980))
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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2D Structure
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SMILES / InChI / InChIKey
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
Natural/Endogenous Targets
Target
OT receptor
V1A receptor
V1B receptor
V2 receptor
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
OT receptor Hs Agonist Full agonist 8.2 – 9.6 pKi - 1,3-5,8-9
pKi 8.2 – 9.6 [1,3-5,8-9]
OT receptor Rn Agonist Full agonist 8.7 pKi - 5
pKi 8.7 [5]
V1A receptor Hs Agonist Full agonist 6.9 – 8.3 pKi - 1,5,13-14,16-19
pKi 6.9 – 8.3 [1,5,13-14,16-19]
V1B receptor Hs Agonist Full agonist 5.7 – 7.0 pKi - 8,14,16-17,19
pKi 5.7 – 7.0 [8,14,16-17,19]
V2 receptor Hs Agonist Full agonist 5.4 – 6.8 pKi - 3,5,14,16-17,19
pKi 5.4 – 6.8 [3,5,14,16-17,19]
V1A receptor Rn Agonist Full agonist 6.1 pKi - 3
pKi 6.1 [3]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Targets where the ligand is described in the comment field
Target Comment
Ligand mentioned in the following text fields