cibinetide   Click here for help

GtoPdb Ligand ID: 9677

Synonyms: ARA 290 | ARA-290 | PH-BSP | PHBSP
Immunopharmacology Ligand
Compound class: Peptide or derivative
Comment: Cibinetide (ARA 290) is an engineered peptide that mimics the 3 dimensional structure of the helix B surface domain of erythropoietin (EPO). It is designed to bind selectively to the non-hematopoietic EPO receptor (sometimes referred to as the innate repair receptor or IRR), that is believed to be a heterodimer of EPOR and the cytokine family beta common receptor (βCR, CD131) [1-2]. Non-hematopoietic EPO ligands have potential tissue protective and anti-inflammatory actions [4-6,8-10]. The IRR is suggested to be a point of integration between the immune system and pain signalling (via nociception) [11].
Cibinetide is SEQ ID NO. 282 (and peptide ID) as claimed in patent WO2009094172 [3].
2D Structure
Click here for help

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.

✖
Click here for structure editor
SMILES / InChI / InChIKey
Click here for help

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.

✖
Canonical SMILES OCC(C(=O)NC(C(=O)O)CO)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C1CCC(=O)N1)CCC(=O)O)CCC(=O)N)CC(C)C)CCC(=O)O)CCCN=C(N)N)C)CC(C)C)CC(=O)N
Isomeric SMILES OC[C@@H](C(=O)N[C@H](C(=O)O)CO)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]1CCC(=O)N1)CCC(=O)O)CCC(=O)N)CC(C)C)CCC(=O)O)CCCN=C(N)N)C)CC(C)C)CC(=O)N
InChI InChI=1S/C51H84N16O21/c1-22(2)17-30(47(84)65-32(19-36(53)71)48(85)66-33(20-68)49(86)67-34(21-69)50(87)88)63-40(77)24(5)57-41(78)25(7-6-16-56-51(54)55)59-43(80)29(11-15-39(75)76)62-46(83)31(18-23(3)4)64-45(82)27(8-12-35(52)70)60-44(81)28(10-14-38(73)74)61-42(79)26-9-13-37(72)58-26/h22-34,68-69H,6-21H2,1-5H3,(H2,52,70)(H2,53,71)(H,57,78)(H,58,72)(H,59,80)(H,60,81)(H,61,79)(H,62,83)(H,63,77)(H,64,82)(H,65,84)(H,66,85)(H,67,86)(H,73,74)(H,75,76)(H,87,88)(H4,54,55,56)/t24-,25-,26-,27-,28-,29-,30-,31-,32-,33-,34-/m0/s1
InChI Key WZTIQQBMSJTRBR-WYKNNRPVSA-N
Peptide Sequence Click here for help
XEQLERALNSS
H-Pyr-Glu-Gln-Leu-Glu-Arg-Ala-Leu-Asn-Ser-Ser-OH
HELM Notation Click here for help
PEPTIDE1{[Glp].E.Q.L.E.R.A.L.N.S.S}$$$$
Chemical Modification
X in the one letter sequence is pyroglutamate (pGlu).
Download 2D Structure Click here for help
Canonical SMILES Download
Isomeric SMILES Download
InChI standard identifier Download
InChI standard key Download

Molecular structure representations generated using Open Babel