MM07   Click here for help

GtoPdb Ligand ID: 8523

Synonyms: cyclo[1-6]CRPRLCHKGPMPF
Comment: MM07, is a cyclic peptide agonist of the apelin receptor that is more stable than the endogenous apelin peptide. It acts as a biased agonist at the apelin receptor, that can preferentially stimulate the G protein pathway. It was hypothesised that this biased action could translate to improved efficacy in vitro by selectively stimulating vasodilatation and inotropic actions, whilst avoiding activation of detrimental β-arrestin-dependent pathways.

HELM annotation for MM07 is PEPTIDE1{C.R.P.R.L.C.H.K.G.P.M.P.F}$PEPTIDE1,PEPTIDE1,1:R3-6:R3$$$. We generated this and the SMILES for MM07 using HELM Editor v1.4 (from Pistoia Alliance). The IUPAC condensed nomenclature is H-Cys(1)-Arg-Pro-Arg-Leu-Cys(1)-His-Lys-Gly-Pro-Met-Pro-Phe-OH.
Click here for help
2D Structure
Click here for help
Click here for structure editor
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES NCCCCC(C(=O)NCC(=O)N1CCCC1C(=O)NC(C(=O)N1CCCC1C(=O)NC(C(=O)O)Cc1ccccc1)CCSC)NC(=O)C(Cc1c[nH]cn1)NC(=O)C1CSSCC(N)C(=O)NC(CCCNC(=N)N)C(=O)N2C(C(=O)NC(C(=O)NC(C(=O)N1)CC(C)C)CCCNC(=N)N)CCC2
Isomeric SMILES NCCCC[C@@H](C(=O)NCC(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)O)Cc1ccccc1)CCSC)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N2[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CC(C)C)CCCNC(=N)N)CCC2
InChI InChI=1S/C67H106N22O14S3/c1-38(2)30-46-57(94)86-49(36-106-105-35-41(69)54(91)81-44(18-10-25-76-67(72)73)63(100)88-27-12-20-51(88)61(98)80-43(56(93)83-46)17-9-24-75-66(70)71)59(96)84-47(32-40-33-74-37-78-40)58(95)79-42(16-7-8-23-68)55(92)77-34-53(90)87-26-11-19-50(87)60(97)82-45(22-29-104-3)64(101)89-28-13-21-52(89)62(99)85-48(65(102)103)31-39-14-5-4-6-15-39/h4-6,14-15,33,37-38,41-52H,7-13,16-32,34-36,68-69H2,1-3H3,(H,74,78)(H,77,92)(H,79,95)(H,80,98)(H,81,91)(H,82,97)(H,83,93)(H,84,96)(H,85,99)(H,86,94)(H,102,103)(H4,70,71,75)(H4,72,73,76)/t41-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-/m0/s1
InChI Key RKFGCZWTURNFPN-SVENNQHVSA-N
Classification Click here for help
Compound class Peptide or derivative
IUPAC Name Click here for help
L-cysteinyl-L-arginyl-L-prolyl-L-arginyl-L-leucyl-L-cysteinyl-L-histidyl-L-lysyl-glycyl-L-prolyl-L-methionyl-L-prolyl-L-phenylalanine (1->6)-disulfide
Synonyms Click here for help
cyclo[1-6]CRPRLCHKGPMPF
Database Links Click here for help
GtoPdb PubChem SID 252166725
PubChem CID 134828250
Search Google for chemical match using the InChIKey RKFGCZWTURNFPN-SVENNQHVSA-N
Search Google for chemicals with the same backbone RKFGCZWTURNFPN
Search UniChem for chemical match using the InChIKey RKFGCZWTURNFPN-SVENNQHVSA-N
Search UniChem for chemicals with the same backbone RKFGCZWTURNFPN

Product suppliers

View disclaimer

Tocris
MM 07
Cat. No. 7053