pe
pep-10390 v1 CC-BY-SA-4.0

Appetite & energy research tool (CHEMBL408257)

A lab-made peptide developed at Eli Lilly to help scientists study how the body controls appetite, energy use, and inflammation; used only as a research tool, not a medicine.

statusbioassayed targetMC3R length4 aa refs1
status 5 / 5
prediction metrics boltz-2 2.2.1
ipTM0.955
pTM0.971
avg pLDDT86.7
ranking score0.884
STRUCTURE · PEP-10390 × MC3R
ranking0.884
target interface 4.5Å peptide drag rotate · ctrl+scroll zoom · right-click pan
boltz-2 2.2.1 · mmCIF ↓ download
sequence4 aa
14
CEWC
in the news 1 article
overview readme

What this is

CHEMBL408257 is a synthetic cyclic peptide developed at Eli Lilly & Company as a laboratory tool for studying melanocortin receptors — a family of receptors that regulate appetite, energy balance, pigmentation, and inflammation. The compound was derived from human beta-melanocyte-stimulating hormone (β-MSH) and engineered to activate both the melanocortin-3 receptor (MC3R) and the melanocortin-4 receptor (MC4R) at subnanomolar concentrations. It is a research ligand, not a drug — it has been tested only in cell-based assays and has not entered human clinical development. Mayer and colleagues described the compound in the Journal of Medicinal Chemistry in 2005.

The platform stores the simplified four-letter sequence CEWC to represent the Cys-Glu-...-Trp-Cys disulfide core of this compound. The actual structure is a 9-residue cyclic peptide (Ac-D-Arg-c[Cys-Glu-D-His-D-Phe-D-Arg-Trp-Cys]-NH₂): N-terminally acetylated, C-terminally amidated, with four D-amino acid substitutions (D-Arg, D-His, D-Phe, D-Arg) and a disulfide bond bridging the two cysteine residues into a ring. None of these modifications — the D-amino acids, the acetyl cap, the C-terminal amide, or the ring-closing disulfide bond — appear in the four-letter stored sequence.

History

The melanocortin-4 receptor (MC4R) emerged in the late 1990s as a major target for anti-obesity drug discovery, after genetic knockout studies in mice showed that MC4R loss causes severe obesity. Researchers at Eli Lilly used human β-MSH (residues 5–22) as a starting scaffold, introducing a disulfide bridge to cyclize the backbone and systematically replacing L-amino acids with D-amino acids and truncating the sequence to improve potency and stability. Mayer and colleagues reported this compound series in 2005 as part of efforts to identify β-MSH-derived agonists with strong MC4R activity; CHEMBL408257 emerged from that series with potent agonism at both MC4R and MC3R.

What it does

CHEMBL408257 activates MC3R and MC4R in cell-based assays, triggering the production of cyclic AMP (cAMP) through Gs-coupled signaling — the same intracellular signal that natural melanocortin peptides produce when they bind these receptors. In functional assays at human receptors, it produced half-maximal cAMP responses at 0.68 nM at MC3R and 0.26 nM at MC4R, with relative efficacies of 87% and 96% respectively (Mayer and colleagues 2005). Binding affinity (Ki) was 33.8 nM at MC3R and 0.44 nM at MC4R, confirming that while the compound activates both receptors potently in functional terms, it binds MC4R considerably more tightly. Activity at MC5R was negligible (Ki > 500 nM), offering selectivity over this peripheral receptor subtype.

MC3R is expressed predominantly in the hypothalamus, where it contributes to the brain's management of energy availability — particularly the timing of feeding relative to caloric cues and the body's response to nutrient deficit. MC4R, in the same region, is the better-characterized driver of appetite suppression and energy expenditure. The compound's dual MC3R/MC4R activity makes it useful as a pharmacological comparator in studies aimed at disentangling the distinct roles of these two closely related receptors.

Evidence

  • Human: No human trials. CHEMBL408257 is a research tool compound; all reported data are from cell-based pharmacology assays.
  • In vitro: Near-full agonist at human MC3R (EC50 = 0.68 nM, relative efficacy 87%) and human MC4R (EC50 = 0.26 nM, relative efficacy 96%) in cAMP release assays; binding Ki = 33.8 nM at MC3R, 0.44 nM at MC4R, > 500 nM at MC5R (Mayer and colleagues 2005).

Mechanism

MC3R and MC4R belong to the melanocortin receptor family — five Gαs-coupled GPCRs (MC1R–MC5R) that share a common set of endogenous ligands derived from proopiomelanocortin (POMC): principally α-MSH, β-MSH, γ-MSH, and ACTH. CHEMBL408257 retains the His-Phe-Arg-Trp pharmacophore core that is conserved across POMC-derived ligands and required for activity across the melanocortin receptor subfamily. The cyclic disulfide scaffold locks this core in a conformation that favors receptor engagement, while D-amino acid substitutions at four positions protect the backbone from proteolytic degradation — a key design advantage over linear natural peptides.

Upon binding MC3R or MC4R, the compound activates adenylyl cyclase via Gαs, elevating intracellular cAMP. Mayer and colleagues identified ring size, ring conformation, and the aromatic character of the D-Phe residue within the disulfide ring as critical determinants of MC4R potency and selectivity in this scaffold series. The endogenous competitive antagonist for both receptors is agouti-related peptide (AgRP), which displaces melanocortin agonists from the binding pocket.

Known effects

  • MC3R agonism (in vitro) — Near-full agonist (87% relative efficacy) at subnanomolar concentration; preclinical research tool only (Mayer and colleagues 2005).
  • MC4R agonism (in vitro) — Higher potency at MC4R than MC3R (EC50 0.26 nM vs 0.68 nM); compound was developed primarily to study the β-MSH-derived MC4R scaffold (Mayer and colleagues 2005).
  • MC5R sparing — Essentially inactive at MC5R (Ki > 500 nM).

Regulatory status

  • US / EU: Not approved. Investigational research compound with no clinical development history.
  • WADA: Not specifically listed; as an unapproved experimental peptide it falls under S0 (non-approved substances).
  • Clinical trials: No trials registered on ClinicalTrials.gov for CHEMBL408257.

Related peptides

  • Melanotan II — a cyclic α-MSH analog that also activates MC3R and MC4R; structurally related scaffold, more widely studied for pigmentation and appetite effects.
  • β-MSH — the natural 22-residue precursor sequence from which CHEMBL408257 was derived.
Hypotheses6 directions▾ collapse

Research directions for this peptide, selected from the current sources — hypotheses you can explore and model. None of it is proven yet; tap any one to see the full thinking.

openupdated 2026-06-05

Does the ring shape of this peptide push the appetite receptor into a mode that keeps signaling longer than normal?

If true, this could point the way to appetite-suppressing drugs that stay effective longer without the body adapting and tuning them out. That would be a significant advance for people managing obesity or metabolic disease.

The hypothesis
This cyclic peptide acts as a biased MC3R agonist, preferentially engaging Gs-cAMP signaling over beta-arrestin recruitment, due to the conformational rigidity imposed by the disulfide ring constraining the Trp pharmacophore in a geometry that favors G-protein coupling over arrestin docking.
Why it’s plausible
Biased agonism at GPCRs is now understood to be conformationally determined: cyclic and conformationally constrained peptides frequently show signaling bias because they stabilize distinct receptor conformations. MC3R signals through Gs (raising cAMP) but can also recruit beta-arrestin, and arrestin-mediated internalization limits the duration of metabolic effect. A rigid disulfide-constrained cyclic peptide is more likely to lock MC3R in a G-protein-preferring conformation than a flexible linear peptide. No biased agonism characterization of this compound appears in the published CHEMBL record.
Why it matters
MC3R-biased agonism toward Gs/cAMP and away from arrestin-mediated desensitization would prolong metabolic signaling duration without receptor downregulation, which is a highly desirable property for a chronic energy-balance therapeutic.
Plausibility.55
Novelty.65
Impact.70
Basis · grounding3 computed/notes
[1]
noteCompound is described as activating MC3R and MC4R in cell-based cAMP assays; no beta-arrestin recruitment data is mentioned, leaving the bias question open.
[2]
sequenceCys-Glu-Trp-Cys disulfide core imposes conformational rigidity on the Trp indole position, which is the primary GPCR-contacting pharmacophore residue in MSH family ligands.
[3]
structureHigh ipTM (0.9548) and pLDDT (86.7) suggest a well-ordered bound conformation, consistent with a rigid ligand that could lock receptor in a preferred signaling state.
openupdated 2026-06-05

Could this peptide reduce harmful inflammation in the brain without changing a person's appetite?

If the anti-inflammatory effect kicks in at lower doses than the appetite effect, the peptide could be useful for brain inflammation conditions, such as those following stroke or severe infection, without causing unwanted metabolic side effects.

The hypothesis
MC3R activation by this cyclic peptide may reduce neuroinflammation independent of its metabolic effects, because MC3R is expressed on microglia and macrophages and its activation suppresses NF-kB-driven cytokine release, suggesting this compound could modulate central inflammatory tone at doses below those required for appetite suppression.
Why it’s plausible
MC3R has a well-documented anti-inflammatory role in peripheral macrophages and, more recently, in CNS microglia. Endogenous MC3R agonists including alpha-MSH and gamma-MSH suppress TNF-alpha and IL-6 through Gs/cAMP/PKA-mediated NF-kB inhibition. A subnanomolar synthetic MC3R agonist with conformational rigidity (likely resistant to proteolysis compared to linear MSH peptides) could exert immunomodulatory effects at concentrations that do not saturate hypothalamic MC3R governing appetite. The compound has only been characterized in cell-based metabolic assays; its anti-inflammatory potential at MC3R has not been explored.
Why it matters
If MC3R-mediated anti-inflammatory activity can be demonstrated at sub-appetite-suppressing doses, this scaffold could be repurposed for neuroinflammatory conditions (e.g., post-ischemic neuroinflammation, sepsis-associated encephalopathy) where appetite modulation is an undesired side effect.
Plausibility.55
Novelty.50
Impact.65
Basis · grounding1 paper · 2 computed/notes
[1]
noteMelanocortin receptors are described as regulating inflammation alongside appetite, energy balance, and pigmentation; the compound was developed as a tool for studying this receptor family broadly.
[2]
paper
Compound characterized in binding and cAMP assays; no inflammatory endpoint data reported, leaving the anti-inflammatory hypothesis untested.
doi: 10.1021/jm0501432
[3]
sequenceDisulfide-constrained cyclic structure (CEWC core) likely confers protease resistance relative to linear MSH peptides, which is a prerequisite for in vivo anti-inflammatory activity at peripheral or CNS sites.
openupdated 2026-06-05

Does one acidic building block in the ring act like a pivot that aims the peptide at one receptor over another?

If this is true, chemists could swap that one building block to steer the peptide toward only the receptor relevant to energy balance, while leaving the pigmentation and other receptors alone. This could make for a cleaner drug with fewer off-target effects.

The hypothesis
The Glu residue within the CEWC disulfide ring acts as a charge-based anchor that orients the Trp indole toward the MC3R transmembrane binding pocket, and neutralizing or replacing Glu with a neutral residue would disproportionately reduce MC3R potency relative to MC4R.
Why it’s plausible
In the MSH/melanocortin receptor interaction literature, the conserved His-Phe-Arg-Trp tetrapeptide core of endogenous ligands is known to make the primary receptor contacts. In the CEWC cyclic core, Glu occupies the position adjacent to Trp and constrained by the disulfide bridge. A negatively charged Glu in a cyclic context can form an intra-ring salt bridge or electrostatic contact that precisely positions the Trp indole. MC3R and MC4R have different charged residues in their binding pockets, so Glu-mediated orientation could differentially favor one over the other. This is testable via the existing subtype selectivity data from the Lilly series.
Why it matters
If Glu is a selectivity-determining positioning residue rather than a direct contact residue, it provides a handle for engineering MC3R-selective analogs without touching the primary pharmacophore, which is a more tractable medicinal chemistry route.
Plausibility.50
Novelty.60
Impact.55
Basis · grounding1 paper · 3 computed/notes
[1]
sequenceThe four stored residues are Cys-Glu-Trp-Cys; Glu is sandwiched between the two disulfide-forming cysteines and the Trp pharmacophore residue.
[2]
structureipTM=0.9548 indicates high-confidence predicted complex with MC3R, suggesting the cyclic core adopts a defined pose where Glu orientation is structurally significant.
[3]
noteCompound activates both MC3R and MC4R at subnanomolar concentrations, meaning the existing potency difference between subtypes is modest and could be amplified by Glu modification.
[4]
paper
Quantitative Ki and EC50 data across subtypes provides the baseline against which Glu-modified analogs would be compared.
doi: 10.1021/jm0501432
openupdated 2026-06-05

Can a four-amino-acid loop bind the appetite-regulating receptor on its own, without the extra pieces around it?

If the small cyclic core is enough to engage the receptor, chemists could build much simpler drugs targeting appetite and energy balance. Simpler molecules are usually cheaper to make and easier to turn into medicines.

The hypothesis
The disulfide-constrained cyclic core CEWC confers MC3R binding affinity that is separable from MC4R affinity, meaning the ring geometry alone, without the four flanking D-amino acids, encodes meaningful receptor subtype discrimination.
Why it’s plausible
The stored sequence CEWC represents only the disulfide-bridged Cys-Glu-Trp-Cys core of a 9-residue cyclic peptide. The full compound is dual MC3R/MC4R agonist at subnanomolar EC50. The D-amino acid substitutions (D-His, D-Phe, D-Arg flanking the core) are known from the MSH scaffold literature to modulate selectivity between MC3R and MC4R. If the core ring itself carries an intrinsic binding pharmacophore for MC3R, then the flanking residues act as selectivity filters rather than primary affinity determinants, a distinction with direct implications for minimal-pharmacophore design.
Why it matters
Identifying the minimal MC3R-binding pharmacophore within a 4-residue cyclic core would enable scaffold reduction strategies that improve selectivity profiles while retaining potency, a persistent challenge in melanocortin drug discovery.
Plausibility.45
Novelty.55
Impact.60
Basis · grounding1 paper · 2 computed/notes
[1]
paper
Ki and EC50 values for MC3R and MC4R binding reported for this compound, establishing subnanomolar dual agonism as the starting benchmark.
doi: 10.1021/jm0501432
[2]
noteFull compound is Ac-D-Arg-c[Cys-Glu-D-His-D-Phe-D-Arg-Trp-Cys]-NH2; the CEWC stored sequence captures only the disulfide-bridged cyclic core.
[3]
structureBoltz-2 complex ipTM=0.9548 at pLDDT=86.7 indicates a well-defined predicted binding pose for the annotated MC3R target, consistent with a stable cyclic conformation driving high-confidence docking.
openupdated 2026-06-05

Are the reversed amino acids responsible for making this peptide avoid receptors that control skin pigmentation and other unrelated functions?

If confirmed, drug designers could use this rule to tune selectivity across the whole melanocortin family. That would matter for anyone developing treatments for obesity or metabolic disease who needs to avoid side effects on skin or glands.

The hypothesis
The four D-amino acid substitutions in the flanking positions (D-Arg1, D-His3, D-Phe4, D-Arg5 of the 9-residue sequence) are primarily responsible for suppressing MC1R and MC5R activity relative to MC3R and MC4R, meaning removal or L-isomer replacement of any single D-residue would re-engage off-target melanocortin subtypes.
Why it’s plausible
Melanocortin receptors MC1R (pigmentation), MC2R (adrenal), MC3R (energy homeostasis), MC4R (satiety), and MC5R (exocrine) share the same endogenous ligand family but differ in their binding pocket geometries. D-amino acid substitutions alter backbone dihedral angles and side-chain projection geometry in ways that can sterically exclude certain receptor subtypes. The β-MSH parent activates all MCRs; the Eli Lilly cyclic compound was engineered for MC3R/MC4R selectivity, and D-substitution is the most structurally distinctive departure from the parent scaffold.
Why it matters
Understanding which D-residues gate MC1R/MC5R activity matters because MC1R activation has distinct anti-inflammatory and pigmentation consequences, and MC5R activation affects sebaceous and exocrine secretion, both are unwanted in an obesity/energy-balance therapeutic context.
Plausibility.60
Novelty.30
Impact.55
Basis · grounding1 paper · 2 computed/notes
[1]
noteCompound derived from human beta-MSH residues 5-22 with four D-amino acid substitutions introduced during medicinal chemistry optimization at Eli Lilly.
[2]
paper
Ki and EC50 values were measured across melanocortin receptor subtypes, establishing the subtype selectivity profile against which individual residue contributions can be evaluated.
doi: 10.1021/jm0501432
[3]
sequenceStored sequence CEWC contains only L-amino acids; the D-residues flanking the core are absent from the stored representation, making this a hypothesis about the full compound structure as described in the readme.
openupdated 2026-06-05

Could this small ring be attached to other therapeutic peptides to add appetite-suppressing activity as a second function?

If the ring can be transplanted, it opens a route to combination drugs that address obesity alongside another condition using a single molecule. That approach could simplify treatment for patients managing multiple metabolic problems at once.

The hypothesis
The CEWC disulfide-bridged core is a portable cyclic scaffold that could be grafted onto non-melanocortin peptide backbones to import MC3R binding activity into otherwise MC3R-inactive sequences, functioning as a transplantable binding module.
Why it’s plausible
Disulfide-constrained cyclic peptide motifs have been successfully used as grafting modules in peptide engineering, most notably in the cystine-knot and sunflower trypsin inhibitor frameworks. The CEWC core is unusually small (4 residues) and achieves subnanomolar MC3R binding in the context of a 9-residue parent peptide. If the core alone carries the binding energy, it represents a minimal and transferable pharmacophore unit. The high predicted interface confidence (ipTM=0.955) is consistent with the core making stable, ordered contacts with MC3R independent of extended flanking sequence.
Why it matters
A portable MC3R-binding ring would allow researchers to add MC3R activation as a secondary function to peptides with other primary activities (e.g., GLP-1 receptor agonists, neuropeptide Y antagonists), enabling the design of multi-target metabolic peptides from modular building blocks.
Plausibility.35
Novelty.70
Impact.55
Basis · grounding1 paper · 2 computed/notes
[1]
structureBoltz-2 ipTM=0.9548 for the CEWC-containing complex with MC3R; high interface confidence for a 4-residue core is consistent with the core itself driving binding.
[2]
noteFull compound is 9 residues; the CEWC disulfide core occupies residues 2-7 of the ring, with only D-Arg flanking on each side, making the core a large fraction of the total binding interface.
[3]
paper
Subnanomolar activity established in cell assays provides the potency benchmark that a grafted CEWC core would need to approach to validate the modular hypothesis.
doi: 10.1021/jm0501432
details expand to inspect
full evidence table1 metrics
metricvaluetool
EC50 0.68 nM GPCRDB/ChEMBL
3-letter notation
Cys-Glu-Trp-Cys
recipeboltz-2 2.2.1
parametervalue
modelboltz-2 2.2.1
weights
hardwarevast_v100_32gb
mlx version
python
random seed1
msa strategycolabfold_local
runtime
predicted by
predicted at2026-05-22
citationbibtex
peptidemodel (2026). Appetite & energy research tool (CHEMBL408257) (pep-10390, v1). PeptideModel. https://peptidemodel.com/card/pep-10390
@peptide{pep10390,
  sequence = {CEWC},
  target   = {mc3r},
  author   = {peptidemodel},
  year     = {2026},
  status   = {bioassayed}
}
clinical trials 0 trials · checked 2026-05-22
0
no registered clinical trials as of 2026-05-22; we'll re-check periodically
references 1 papers
[1]
Discovery of a β-MSH-Derived MC-4R Selective Agonist
Mayer, J. et al. Journal of Medicinal Chemistry 2005
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