[3H]AVP (human, mouse, rat)   Click here for help

GtoPdb Ligand ID: 2175

Synonyms: [3H]arginine vasopressin
 Ligand is labelled  Ligand is radioactive
Compound class: Peptide
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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
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 SCC(C(=O)N1CCCC1C(=O)NC(C(=O)NCC(=O)N)CCCN=C(N)N)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(CS)N)Cc1ccc(cc1)O)Cc1ccccc1)CCC(=O)N)CC(=O)N
Isomeric SMILES NC(=O)CC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](N)CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O
InChI InChI=1S/C46H67N15O12S2/c47-27(22-74)38(66)57-30(19-25-10-12-26(62)13-11-25)42(70)58-31(18-24-6-2-1-3-7-24)41(69)55-29(14-15-35(48)63)40(68)59-32(20-36(49)64)43(71)60-33(23-75)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/h1-3,6-7,10-13,27-34,62,74-75H,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 MIFHTMACYGHZKT-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/)
References
1. Breton C, Chellil H, Kabbaj-Benmansour M, Carnazzi E, Seyer R, Phalipou S, Morin D, Durroux T, Zingg H, Barberis C et al.. (2001)
Direct identification of human oxytocin receptor-binding domains using a photoactivatable cyclic peptide antagonist: comparison with the human V1a vasopressin receptor.
J Biol Chem, 276 (29): 26931-41. [PMID:11337500]
2. Chini B, Mouillac B, Ala Y, Balestre MN, Trumpp-Kallmeyer S, Hoflack J, Elands J, Hibert M, Manning M, Jard S et al.. (1995)
Tyr115 is the key residue for determining agonist selectivity in the V1a vasopressin receptor.
EMBO J, 14 (10): 2176-82. [PMID:7774575]
3. Cotte N, Balestre MN, Phalipou S, Hibert M, Manning M, Barberis C, Mouillac B. (1998)
Identification of residues responsible for the selective binding of peptide antagonists and agonists in the V2 vasopressin receptor.
J Biol Chem, 273 (45): 29462-8. [PMID:9792651]
4. Derick S, Cheng LL, Voirol MJ, Stoev S, Giacomini M, Wo NC, Szeto HH, Ben Mimoun M, Andres M, Gaillard RC et al.. (2002)
[1-deamino-4-cyclohexylalanine] arginine vasopressin: a potent and specific agonist for vasopressin V1b receptors.
Endocrinology, 143 (12): 4655-64. [PMID:12446593]
5. Nakamura S, Yamamura Y, Itoh S, Hirano T, Tsujimae K, Aoyama M, Kondo K, Ogawa H, Shinohara T, Kan K et al.. (2000)
Characterization of a novel nonpeptide vasopressin V(2)-agonist, OPC-51803, in cells transfected human vasopressin receptor subtypes.
Br J Pharmacol, 129 (8): 1700-6. [PMID:10780976]
6. Saito M, Tahara A, Sugimoto T. (1997)
1-desamino-8-D-arginine vasopressin (DDAVP) as an agonist on V1b vasopressin receptor.
Biochem Pharmacol, 53: 1711-1717. [PMID:9264324]
7. Tahara A, Saito M, Sugimoto T, Tomura Y, Wada K, Kusayama T, Tsukada J, Ishii N, Yatsu T, Uchida W et al.. (1998)
Pharmacological characterization of YM087, a potent, nonpeptide human vasopressin V1A and V2 receptor antagonist.
Naunyn Schmiedebergs Arch Pharmacol, 357 (1): 63-9. [PMID:9459574]
8. Tahara A, Saito M, Sugimoto T, Tomura Y, Wada K, Kusayama T, Tsukada J, Ishii N, Yatsu T, Uchida W et al.. (1998)
Pharmacological characterization of the human vasopressin receptor subtypes stably expressed in Chinese hamster ovary cells.
Br J Pharmacol, 125 (7): 1463-70. [PMID:9884074]
9. Thibonnier M, Auzan C, Madhun Z, Wilkins P, Berti-Mattera L, Clauser E. (1994)
Molecular cloning, sequencing, and functional expression of a cDNA encoding the human V1a vasopressin receptor.
J Biol Chem, 269 (5): 3304-10. [PMID:8106369]
10. Thibonnier M, Preston JA, Dulin N, Wilkins PL, Berti-Mattera LN, Mattera R. (1997)
The human V3 pituitary vasopressin receptor: ligand binding profile and density-dependent signaling pathways.
Endocrinology, 138 (10): 4109-22. [PMID:9322919]
11. Yamamura Y, Nakamura S, Itoh S, Hirano T, Onogawa T, Yamashita T, Yamada Y, Tsujimae K, Aoyama M, Kotosai K et al.. (1998)
OPC-41061, a highly potent human vasopressin V2-receptor antagonist: pharmacological profile and aquaretic effect by single and multiple oral dosing in rats.
J Pharmacol Exp Ther, 287 (3): 860-7. [PMID:9864265]