pe
pep-10695 v1 CC-BY-SA-4.0

Frog-skin painkiller peptide (D-Met2-Deltorphin)

A natural peptide from a Brazilian tree frog's skin that binds opioid receptors and is used to study pain pathways in the lab, a research tool, not an approved drug.

statussynthesized targetOPRM1 length8 aa refs2
status 4 / 5
prediction metrics boltz-2 1.0
ipTM0.958
pTM0.885
avg pLDDT77.2
ranking score0.810
STRUCTURE · PEP-10695 × OPRM1
ranking0.810
target interface 4.5Å peptide drag rotate · ctrl+scroll zoom · right-click pan
boltz-2 1.0 · mmCIF ↓ download
sequence8 aa
158
YDMFHLMD
overview readme

What this is

D-Met2-Deltorphin is a seven-amino-acid opioid peptide originally isolated from the skin glands of the Jandaia leaf frog (Phasmahyla jandaia), a phyllomedusine tree frog endemic to the southern Espinhaço mountain range in Brazil. It belongs to the deltorphin family — a group of naturally occurring peptides notable for carrying an unusually rare D-amino acid at the second position of their sequence, a feature that gives them exceptional binding properties at opioid receptors. The peptide has no approved medical use and is used primarily as a pharmacological research tool.

The stored sequence YDMFHLMD is the bare eight-residue backbone. The active form carries a C-terminal amide (-NH₂) not visible in the raw sequence, and the methionine at position 2 is in the D-configuration (D-Met²) — encoded as a standard M in the stored letters. Both features are central to the peptide's receptor-binding behaviour.

History

The deltorphin family was first brought to scientific attention in 1989 through near-simultaneous reports from several groups. Kreil and colleagues coined the name "deltorphin" for these delta-receptor-preferring peptides isolated from Phyllomedusa sauvagei skin, and Erspamer and colleagues (PNAS 1989) characterized a family of heptapeptides from the same source with higher affinity and selectivity for delta-opioid binding sites than any natural compound known at the time. That same year, Lazarus and colleagues (JBC 1989) characterised a related variant, [D-Met²] dermorphin gene-associated peptide (DGAP), and found it carried high delta-selectivity — measurements showed an IC50 of 0.80 nM at delta receptors and greater than 1 µM at mu receptors, a selectivity ratio of approximately 1345.

Phasmahyla jandaia is a distinct frog species within the broader Phyllomedusinae subfamily. In 2011, Rates and colleagues published a systematic peptidomic survey of this frog's skin secretion, sequencing 57 peptides by tandem mass spectrometry and Edman N-terminal sequencing, and confirmed that the skin contains opioid peptides including D-Met2-Deltorphin alongside antimicrobial peptides (phylloseptins, dermaseptins, dermatoxins), bradykinin-related compounds, and several peptide families without similarity to any previously known molecules (Rates and colleagues, Toxicon 2011).

What it does

Deltorphins act primarily as agonists at delta-opioid receptors, triggering the inhibitory signalling cascade associated with reduced neuronal excitability. The common N-terminal sequence Tyr-D-Xaa-Phe shared by all amphibian opioid peptides appears to function as the "message" motif that engages opioid receptors; the C-terminal residues determine which receptor subtype is preferentially activated. In deltorphins, including the D-Met² form, the C-terminal region steers selectivity toward delta rather than mu receptors — in contrast to the related frog peptide dermorphin (/card/pep-10694), which carries a C-terminal sequence that confers mu selectivity.

Beyond direct receptor activation, D-Met2-Deltorphin has been used as a research tool to probe how opioid receptor subtypes differ in their intracellular fate after activation. Schulz and colleagues (JPET 2002) used fluorescently-tagged delta and mu receptor constructs in live cells to show that delta-opioid receptor activation triggers rapid translocation of G-protein-coupled receptor kinases (GRK2 and GRK3) to the cell membrane, with the result that delta receptors and GRKs cointernalize together into intracellular vesicles. Mu-opioid receptors, by contrast, also internalize upon activation but did not cointernalize with GRK2 or GRK3 in the same system — a mechanistically distinct profile that affects receptor resensitization and tolerance.

Evidence

  • Human: No human trials identified for D-Met2-Deltorphin.
  • Animal: The deltorphin family has been studied in rodent models of analgesia; the naturally occurring D-amino acid confers protease resistance relative to L-amino-acid sequences.
  • In vitro: Binding studies report high delta-opioid receptor affinity for the D-Met² deltorphin variant (Lazarus and colleagues, JBC 1989). Schulz and colleagues (JPET 2002) demonstrated differential GRK2/3 cointernalization between delta and mu opioid receptors in transfected HEK293 and neuroblastoma-glioma cells.

Known effects

  • Delta-opioid receptor agonism — Pharmacological characterization; high delta selectivity in binding assays (Lazarus and colleagues 1989)
  • Differential receptor internalization — Delta receptors cointernalize with GRK2/3; mu receptors do not (Schulz and colleagues 2002)
  • Protease resistance — Conferred by the D-amino acid at position 2; common to this peptide family

Mechanism

D-Met2-Deltorphin shares the conserved Tyr-D-Xaa-Phe motif at the N-terminus with other frog-skin opioid peptides, which serves as the minimal pharmacophore for opioid receptor engagement. The D-methionine at position 2 (D-Met²) stabilises a bioactive conformation that favours delta-opioid receptor binding over mu-opioid receptor binding. Delta-opioid receptors are class A GPCRs that signal primarily through Gαi/o proteins, inhibiting adenylate cyclase and reducing intracellular cAMP.

In live-cell fluorescence microscopy studies, delta-opioid receptor activation promoted Gβγ-dependent recruitment of GRK2 and GRK3 from the cytosol to the plasma membrane; treatment with phosducin (a Gβγ scavenger) blocked this translocation, confirming the G-protein dependence of the process (Schulz and colleagues, JPET 2002). The resulting cointernalization of delta receptors with GRKs distinguishes delta from mu receptors and has implications for how each receptor type desensitises and re-sensitises after repeated agonist exposure — a mechanistic difference relevant to tolerance research.

Related peptides

  • Dermorphin — the mu-selective counterpart from Phyllomedusa sauvagei skin; shares the Tyr-D-Xaa-Phe N-terminal motif but carries a C-terminal sequence that confers mu rather than delta selectivity
Hypotheses5 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 2026-06-11

Is D-Met2-Deltorphin actually a delta-opioid selective peptide that has been mislabeled as a mu-opioid ligand?

If true, this peptide would be correctly recognized as a precision tool for studying the delta opioid system, which is linked to mood and chronic pain, potentially guiding development of non-addictive pain treatments.

The hypothesis
The annotated target oprm1 (mu-opioid receptor) is incorrect for D-Met2-Deltorphin; the peptide's primary high-affinity target is oprd1 (delta-opioid receptor), and the high ipTM of 0.9578 with oprm1 reflects structural similarity between mu and delta receptor binding pockets rather than true mu selectivity.
Why it’s plausible
Deltorphins were historically characterized as having the highest delta-selectivity of any natural compound (Erspamer et al., PNAS 1989). The D-Met2 substitution and C-terminal amide are hallmarks of delta-preferring frog peptides. A high complex ipTM against oprm1 could arise because mu and delta opioid receptors share a highly conserved orthosteric binding pocket, making cross-docking plausible without reflecting pharmacological selectivity.
Why it matters
If the peptide is misannotated as a mu-ligand, downstream research using it as an mu-opioid probe would generate misleading data; correctly repositioning it as a delta-selective tool compound has direct consequences for pain and addiction pharmacology.
Plausibility.95
Novelty.45
Impact.85
Basis · grounding2 computed/notes
[1]
noteREADME states deltorphins were characterized as having higher affinity and selectivity for delta-opioid binding sites than any natural compound known at the time, while the card annotates target as oprm1 (mu receptor).
[2]
structureboltz-2 complex ipTM=0.9578 with oprm1; high score may reflect conserved GPCR orthosteric pocket geometry shared between mu and delta receptors rather than true selectivity.
openupdated 2026-06-11

Does the frog peptide's resistance to being broken down make it drive receptor desensitization longer than the body's own opioid molecules?

If true, this would help explain why tolerance to delta-opioid drugs develops and could point to dosing strategies that minimize tolerance for people needing long-term pain management.

The hypothesis
D-Met2-Deltorphin drives pronounced delta-opioid receptor (OPRD1) internalization and receptor desensitization upon repeated dosing, but because the C-terminal amide slows its proteolytic clearance, the peptide produces longer-lasting receptor downregulation than endogenous enkephalins, which could underlie tolerance distinct from mu-opioid tolerance.
Why it’s plausible
The literature snippet (10.1124/jpet.300.2.376) specifically discusses internalization of delta-opioid receptors in real-time confocal experiments. Deltorphins are known full agonists at OPRD1. The C-terminal amide slows carboxypeptidase cleavage, prolonging receptor occupancy. Sustained delta-receptor occupancy is associated with internalization and beta-arrestin recruitment, which differs mechanistically from mu-receptor tolerance.
Why it matters
If prolonged OPRD1 downregulation is a feature of this peptide's profile, it would have implications for the therapeutic window of any delta-opioid drug derived from this scaffold and for understanding cross-tolerance with mu-opioid analgesics.
Plausibility.75
Novelty.55
Impact.70
Basis · grounding1 paper · 1 computed/note
[1]
paper
Paper directly examines delta-opioid receptor internalization dynamics using fluorescent receptor tracking, suggesting this is a documented phenomenon relevant to deltorphin-class ligands.
doi: 10.1124/jpet.300.2.376
[2]
noteC-terminal amide is noted as central to receptor-binding behaviour; amidation is a known proteolytic protection strategy that extends peptide half-life and sustained receptor engagement.
openupdated 2026-06-11

Does the mirror-image amino acid at position 2 force the peptide into a specific bent shape that lines up its two key aromatic residues (Tyr1 and Phe3) to fit the delta opioid receptor?

If confirmed, this could guide the design of smaller, more stable molecules that copy just the active turn of the frog peptide, a possible route to new options for chronic pain.

The hypothesis
The D-amino acid at position 2 (D-Met2) stabilizes a backbone turn between residues 1-3 that positions the Tyr1 side chain and the Phe4 aromatic ring in a geometry required for high-affinity delta-opioid receptor engagement, and this turn geometry cannot be achieved by the all-L analog.
Why it’s plausible
D-amino acids at position 2 of opioid peptides are known to introduce a beta-turn or gamma-turn that orients the N-terminal Tyr and a downstream aromatic residue for receptor binding. The sequence YDMFHLMD contains Tyr1 and Phe4, matching the classical opioid message sequence pharmacophore. The D-configuration at position 2 would force a different phi/psi space than L-Met, potentially locking this pharmacophore into a receptor-complementary conformation.
Why it matters
Confirming this turn geometry would explain why D-Met2 confers both potency and delta-selectivity, enabling rational design of minimized peptidomimetics that retain this scaffold without the full 8-residue sequence.
Plausibility.70
Novelty.55
Impact.70
Basis · grounding2 computed/notes
[1]
sequenceSequence YDMFHLMD: Tyr1 and Phe4 form a classic opioid message-sequence aromatic pair; D-Met at position 2 is encoded as standard M but noted in README as D-configuration, creating a non-standard backbone dihedral that would influence the Tyr1-Phe4 spatial arrangement.
[2]
noteREADME explicitly states D-Met2 and C-terminal amide are central to receptor-binding behaviour, implying the stereochemistry at position 2 is a key structural determinant.
openupdated 2026-06-11

If the unusual D-amino acid at position 2 is swapped for other mirror-image building blocks, can the peptide's receptor preference be precisely controlled?

If the pattern holds, chemists could use this rule to create a family of stable, selective opioid peptides tailored to specific receptor subtypes, potentially improving pain treatment while reducing addiction risk.

The hypothesis
Replacing D-Met2 with other D-amino acids bearing smaller or bulkier side chains (D-Ala, D-Leu, D-Phe) would shift the pharmacophore turn angle measurably and produce a predictable gradient of delta/mu binding ratio, enabling a structure-activity map from a single position that is currently absent for this deltorphin variant.
Why it’s plausible
The D-configuration at position 2 is the only non-standard chemical feature encoded in the stored sequence (the C-terminal amide is not in the SMILES/sequence). Systematic D-amino acid substitution at position 2 is a classic opioid peptide SAR strategy, but the specific contribution of the Met side chain bulk and sulfur polarity to selectivity for D-Met2-Deltorphin specifically has not been systematically mapped. Different D-residues would alter steric bulk and polarity of the turn without altering the message-sequence Tyr1 or Phe4 pharmacophores.
Why it matters
Identifying which D-amino acid at position 2 maximizes delta selectivity while maintaining potency would provide a directly actionable engineering rule for designing protease-stable delta-selective analgesics derived from this scaffold.
Plausibility.78
Novelty.40
Impact.70
Basis · grounding2 computed/notes
[1]
sequenceSequence YDMFHLMD: D-Met at position 2 is structurally critical per README; Met has a flexible thioether side chain that differs in steric and electronic properties from Ala, Leu, or Phe, suggesting side-chain identity at this position is under-explored for this variant.
[2]
noteREADME notes D-amino acid at position 2 gives exceptional binding properties; no SAR data on position-2 side-chain identity is mentioned, indicating this is an unexplored axis.
openupdated 2026-06-11

Could this protease-resistant frog peptide, by activating delta opioid receptors on microglia, dampen harmful inflammation in the brain after injury?

If true, this peptide could be a starting point for treatments targeting brain inflammation after stroke or head injury, conditions with few effective options today.

The hypothesis
D-Met2-Deltorphin may modulate neuroinflammation independently of classical opioid receptor signaling through activation of delta-opioid receptors on microglia, potentially suppressing pro-inflammatory cytokine release in central nervous system injury contexts where endogenous delta-opioid tone is insufficient.
Why it’s plausible
Delta-opioid receptors are expressed on microglia and astrocytes, and their activation has been linked to neuroprotective and anti-inflammatory effects beyond analgesia. D-Met2-Deltorphin's resistance to proteolysis (D-amino acid + C-terminal amide) makes it viable in the CNS environment. If its selectivity is truly at OPRD1, it could engage glial delta receptors in a way that endomorphins or enkephalins, which are rapidly degraded, cannot sustain.
Why it matters
A protease-resistant delta-opioid agonist with CNS access could serve as a candidate neuroprotective agent for conditions like traumatic brain injury or stroke, applications not explored for deltorphin-class peptides from this frog.
Plausibility.60
Novelty.60
Impact.65
Basis · grounding1 paper · 1 computed/note
[1]
noteREADME describes D-amino acid and C-terminal amide as key to binding and implicitly to stability; proteolytic resistance in CNS extracellular space would be a prerequisite for any neuroinflammatory application.
[2]
paper
Paper studies delta-opioid receptor signaling and internalization; delta receptor biology in non-neuronal CNS cells is an active extension of this receptor system relevant to neuroinflammation.
doi: 10.1124/jpet.300.2.376
details expand to inspect
full evidence table2 metrics
metricvaluetool
ipTM 0.9578285813331604 boltz-2
ranking score 0.8095315098762512 boltz-2
structural qualityopenfold3
metricvaluenote
gpde0.615global PDE — lower = better
disorderNaNfraction disordered
3-letter notation
Tyr-Asp-Met-Phe-His-Leu-Met-Asp
recipeboltz-2 1.0
parametervalue
modelboltz-2 1.0
weights
hardwarenvidia_nim_api
mlx version
python
random seed
msa strategynone
diffusion samples1
runtime
predicted bymlx@peptide
predicted at2026-04-24
citationbibtex
peptidemodel (2026). Frog-skin painkiller peptide (D-Met2-Deltorphin) (pep-10695, v1). PeptideModel. https://peptidemodel.com/card/pep-10695
@peptide{pep10695,
  sequence = {YDMFHLMD},
  target   = {oprm1},
  author   = {peptidemodel},
  year     = {2026},
  status   = {synthesized}
}
related peptides 1 by signal overlap
clinical trials 0 trials · checked 2026-05-09
0
no registered clinical trials as of 2026-05-09; we'll re-check periodically
references 2 papers
discussion no comments
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peptidemodel.com CC-BY-SA-4.0 research only · not for human use