pe
pep-10413 v1 CC-BY-SA-4.0

Opioid receptor research tool (Ac-YKWW-NH₂ / CHEMBL102690)

A synthetic four-amino-acid peptide that weakly binds opioid receptors; used only as a lab research tool to study how peptide structure affects opioid activity.

statusbioassayed targetOPRD1 length4 aa refs1
status 5 / 5
prediction metrics boltz-2 1.0
ipTM0.893
pTM0.834
avg pLDDT80.6
ranking score0.824
STRUCTURE · PEP-10413 × OPRD1
ranking0.824
target interface 4.5Å peptide drag rotate · ctrl+scroll zoom · right-click pan
boltz-2 1.0 · mmCIF ↓ download
sequence4 aa
14
YKWW
overview readme

What this is

Ac-YKWW-NH₂ is a synthetic tetrapeptide — four amino acids long — studied as a research tool in opioid receptor pharmacology. It was synthesized and tested by Wan, Murray, and Aldrich (Journal of Medicinal Chemistry, 1999) as part of an effort to explore acetylated peptide analogues of dynorphin A, an endogenous opioid. The compound carries an N-terminal acetyl cap and a C-terminal amide group; the raw four-letter sequence YKWW does not reflect these modifications. It binds weakly and without selectivity to all three classical opioid receptor subtypes — delta (OPRD1), mu (OPRM1), and kappa — making it primarily a reference point in structure-activity relationship (SAR) research rather than a drug candidate.

What it does

At the delta opioid receptor (OPRD1), Ac-YKWW-NH₂ shows a Ki of 3,478 nM — roughly 3.5 micromolar — indicating very weak binding affinity. The compound also binds the mu (OPRM1) and kappa opioid receptors with similarly low affinity (Ki 3,590 nM and 1,367 nM respectively), with no meaningful selectivity across the three subtypes. All three values were measured by radioligand displacement: [³H]-DPDPE for delta, [³H]-DAMGO for mu, and [³H]-diprenorphine for kappa (Wan, Murray, and Aldrich, 1999).

Evidence

  • Human: No human data. This compound has not been evaluated in human subjects.
  • Animal: No animal data. All reported data are from cell-membrane binding assays.
  • In vitro: Radioligand binding assays against opioid receptors: Ki (OPRD1, delta) = 3,478 nM; Ki (OPRM1, mu) = 3,590 nM; Ki (OPRK1, kappa) = 1,367 nM (Wan, Murray, and Aldrich, Journal of Medicinal Chemistry, 1999).

Mechanism

Opioid receptors are G protein-coupled receptors (GPCRs) expressed throughout the central and peripheral nervous system. Their endogenous peptide ligands — enkephalins (delta-preferring), endorphins (mu-preferring), and dynorphins (kappa-preferring) — all share the N-terminal motif Tyr-Gly-Gly-Phe, which acts as the receptor-activating "message sequence." Ac-YKWW-NH₂ retains the N-terminal tyrosine but replaces the Gly-Gly-Phe core with Lys-Trp-Trp, and blocks the free N-terminus with an acetyl group — a departure from the canonical pharmacophore that likely accounts for its weak, non-selective receptor engagement. The compound was part of an early SAR exploration by the Aldrich group into acetylated dynorphin A analogues, a programme that subsequently identified more potent and selective kappa-targeted peptides.

Related peptides

  • Arodyn (Ac[Phe¹,²,³,Arg⁴,D-Ala⁸]Dyn A-(1–11)-NH₂) is an 11-residue acetylated dynorphin A analogue from the same research programme, later identified as a selective kappa opioid receptor antagonist (Bennett, Murray, and Aldrich, 2002).
  • Met-enkephalin (Tyr-Gly-Gly-Phe-Met) and Leu-enkephalin (Tyr-Gly-Gly-Phe-Leu) are endogenous delta-preferring opioid pentapeptides whose Tyr-Gly-Gly-Phe message sequence Ac-YKWW-NH₂ structurally departs from.
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 2026-06-05

If a short positively charged sequence is attached to YKWW, will the resulting peptide bind only the kappa opioid receptor?

A kappa-selective peptide could potentially treat chronic pain and severe itch without triggering the euphoria and dependence associated with mu-receptor drugs like morphine, offering a safer option for patients with conditions poorly served by current opioids.

The hypothesis
Ac-YKWW-NH2 represents a minimal 'address-free' opioid pharmacophore, and appending a short address sequence derived from dynorphin A (e.g., Arg-Arg-Ile) to its C-terminus would confer kappa selectivity without abolishing binding, because the kappa receptor's extracellular loop 2 accommodates basic residues from dynorphin's address domain.
Why it’s plausible
The dynorphin A model proposes a two-domain structure: a Tyr-Gly-Gly-Phe 'message' for activation and a basic 'address' for selectivity at OPRK1. YKWW, as a truncated dynorphin analogue with a Tyr message residue, lacks the address. Dynorphin A residues 5-9 (RRIRP) are arginine-rich and confer kappa preference. Grafting a minimal basic address onto YKWW could convert a non-selective scaffold into a kappa-selective one. The four-residue Ac-YKWW-NH2 is already acetylated and amidated, meaning synthetic extension at the C-terminus (before amidation) is chemically feasible.
Why it matters
Kappa agonists are pursued for pain, pruritus, and mood disorders; a minimal, readily synthesised kappa-selective scaffold derived from YKWW would be a tractable lead for peptide drug development.
Plausibility.55
Novelty.45
Impact.60
Basis · grounding1 paper · 3 computed/notes
[1]
noteAc-YKWW-NH2 was synthesised as part of dynorphin A SAR work (Wan, Murray, Aldrich 1999), situating it in the message-address framework
[2]
noteOPRK1 Ki 1367 nM is the lowest measured, suggesting residual kappa compatibility in the scaffold
[3]
paper
Wan et al. JMedChem 1999: systematic acetylated dynorphin A analogue series, providing the SAR context for address-domain effects
doi: 10.1021/jm9901071
[4]
sequenceYKWW retains Tyr at position 1, the message-domain pharmacophore; C-terminal Trp-Trp is compact enough that address extension would not create steric clash at the N-terminal binding site
openupdated 2026-06-05

Do the two tryptophan amino acids at the end of YKWW grip the opioid receptor in a way that is shared by all three receptor types?

If confirmed, chemists would know exactly which part of the molecule to keep untouched and which part to modify when designing new, more targeted opioid drugs, shortening the drug discovery process.

The hypothesis
The double-Trp C-terminus (positions 3 and 4) of YKWW acts as a hydrophobic anchor that stabilises the peptide within the opioid receptor transmembrane bundle, and replacing either Trp with a less bulky residue would disproportionately reduce all three receptor affinities rather than shifting selectivity.
Why it’s plausible
Endogenous opioid peptides carry a conserved Tyr-Gly-Gly-Phe N-terminal message sequence; YKWW deviates by substituting Gly-Gly-Phe with Lys-Trp-Trp. The two contiguous Trp residues are unusual and highly hydrophobic. In solved structures of opioid receptors, the binding pocket is predominantly hydrophobic in the lower transmembrane region. A tandem Trp pair could fill this pocket via pi-stacking or van der Waals contacts in a way that a single Phe cannot. The high ipTM (0.893) for the complex supports a well-packed interface.
Why it matters
Establishing that the WW motif is a general hydrophobic anchor rather than a selectivity determinant would clarify why this peptide lacks selectivity and would guide SAR: selectivity would need to come from the Tyr or Lys positions, not the C-terminus.
Plausibility.60
Novelty.40
Impact.45
Basis · grounding3 computed/notes
[1]
sequencePositions 3 and 4 are both Trp (W), the largest natural amino acid by sidechain volume; tandem Trp is rare in endogenous opioid peptides
[2]
noteBinding is non-selective across all three subtypes, consistent with a non-discriminating hydrophobic contact rather than subtype-specific polar interactions
[3]
structurepLDDT 80.6 and ipTM 0.893 indicate a structured, confident predicted complex, suggesting the Trp pair does form stable contacts
openupdated 2026-06-05

Is the single positively charged amino acid in YKWW preventing the peptide from binding one opioid receptor much more strongly than the others?

If removing that one amino acid reveals selectivity, it would accelerate the design of opioid drugs that hit only the desired receptor, reducing side effects for pain and mood disorder patients.

The hypothesis
The lysine at position 2 of YKWW is the primary determinant of the peptide's failure to achieve selectivity, because its positive charge at physiological pH occupies a polar sub-pocket that is similarly sized across OPRD1, OPRM1, and OPRK1, and substituting it with a neutral residue (e.g., norleucine) would break this degeneracy and reveal a latent selectivity profile.
Why it’s plausible
Position 2 in the endogenous opioid message sequence is typically Gly (in enkephalins) or a small residue. YKWW replaces this with Lys, introducing a long positively charged sidechain. All three classical opioid receptors contain conserved acidic or polar residues in the orthosteric binding pocket (e.g., Asp128 in OPRD1, equivalent residues in OPRM1/OPRK1) that could interact non-discriminately with Lys-2, masking any subtype selectivity conferred by positions 3-4. Neutralising this contact should allow positions 3-4 (Trp-Trp) to exert differential subtype discrimination.
Why it matters
Understanding whether Lys-2 suppresses or enables selectivity is a concrete, testable SAR question with direct implications for how to optimise the YKWW scaffold into a selective probe.
Plausibility.50
Novelty.50
Impact.50
Basis · grounding1 paper · 2 computed/notes
[1]
sequencePosition 2 is Lys (K), a residue with a long, flexible, charged sidechain not found at position 2 in enkephalin or endorphin message sequences
[2]
noteAll three Ki values are within a 3-fold window (1367-3590 nM), consistent with a common polar contact dominating the binding energy and obscuring differential contacts at other positions
[3]
paper
Wan et al. JMedChem 1999 SAR series; analogue context allows inference about position-specific contributions
doi: 10.1021/jm9901071
openupdated 2026-06-05

Does the YKWW tetrapeptide bind the kappa opioid receptor for a structural reason that could be exploited to build a selective kappa drug?

If true, researchers would have a tiny, chemically simple starting point for kappa-selective painkillers, which could relieve pain and itch without the dependence risk of drugs like morphine, benefiting patients and prescribers alike.

The hypothesis
The kappa opioid receptor (OPRK1) is the primary binding partner of Ac-YKWW-NH2, and the roughly 2.5-fold preference for kappa (Ki 1,367 nM) over delta (Ki 3,478 nM) and mu (Ki 3,590 nM) reflects a structural compatibility between the YKWW core and kappa-specific binding pocket residues not shared by the other two subtypes.
Why it’s plausible
The kappa Ki is consistently the lowest of the three measured values by a factor of approximately 2.5. This is not random noise; in a series of acetylated dynorphin A analogues, kappa selectivity traces to dynorphin A's known kappa preference. YKWW preserves the Tyr-1 and Trp residues that are pharmacophoric in kappa-active dynorphin fragments. The boltz-2 complex ipTM of 0.893 indicates a confident predicted binding pose, suggesting the four-residue scaffold does form a stable interface with at least one receptor conformation.
Why it matters
If YKWW's kappa lean is sequence-determined rather than incidental, it provides a minimal four-residue kappa-preferring scaffold that could be elongated or decorated to reach true kappa selectivity, a valuable goal given kappa's role in pain, itch, and depression without the addiction liability of mu agonism.
Plausibility.55
Novelty.35
Impact.45
Basis · grounding1 paper · 3 computed/notes
[1]
noteKi values: OPRD1 3478 nM, OPRM1 3590 nM, OPRK1 1367 nM from radioligand displacement (Wan, Murray, Aldrich 1999)
[2]
paper
Wan, Murray, Aldrich JMedChem 1999 SAR study of acetylated dynorphin A analogues
doi: 10.1021/jm9901071
[3]
structureboltz-2 complex ipTM 0.893, pLDDT 80.6, indicating confident predicted receptor-bound conformation
[4]
sequenceYKWW: Tyr-1 is the canonical opioid pharmacophore 'message' residue; two Trp residues at positions 3-4 are bulky aromatic, consistent with kappa pocket tolerance for large sidechains
openupdated 2026-06-05

Does YKWW actually switch on opioid receptors, or does it sit in the binding site without triggering a signal?

If YKWW turns out to partially block opioid receptors, it could be developed as a template for drugs that dampen opioid signalling, potentially useful in treating opioid overdose or addiction with fewer withdrawal side effects than existing blockers like naloxone.

The hypothesis
Ac-YKWW-NH2 is likely a partial agonist or biased antagonist at all three opioid receptors rather than a full agonist, because its extremely low binding affinity (micromolar Ki) coupled with an acetylated N-terminus and bulky C-terminal Trp-Trp pair would sterically preclude the receptor conformational change required for full G-protein coupling, favouring arrestin-biased or inactive receptor states.
Why it’s plausible
Full opioid agonism requires the Tyr-1 hydroxyl to engage Asp of TM3 and trigger a specific receptor conformational shift. In enkephalins and morphine, high-affinity binding (low nanomolar) drives this shift. At micromolar affinity, occupancy at the orthosteric site is insufficient to drive full activation under physiological conditions. Furthermore, N-terminal acetylation removes the free amine that makes a cation-pi contact with Trp293 (OPRM1 equivalent), a contact critical for agonist-induced conformational change. The Trp-Trp pair may additionally wedge into an extended pose that stabilises an inactive receptor conformation, a mechanism seen in peptide antagonists with bulky C-termini.
Why it matters
If YKWW is a weak partial agonist or functional antagonist, it would be relevant as a low-efficacy reference standard in functional assays and could serve as a biased-signalling probe to dissect G-protein vs arrestin pathways at opioid receptors.
Plausibility.45
Novelty.30
Impact.40
Basis · grounding4 computed/notes
[1]
noteAll Ki values are in the micromolar range (1367-3590 nM); no functional (cAMP, GTPgammaS, arrestin) data reported, leaving efficacy unknown
[2]
noteN-terminal acetyl cap is present, blocking the free amine that contributes to agonist-state stabilisation in opioid receptors
[3]
sequenceTrp at positions 3 and 4 are the two largest natural sidechains; tandem Trp C-terminus is not found in any known full opioid agonist
[4]
structureipTM 0.893 indicates the peptide does dock stably, but pLDDT 80.6 (moderate) is consistent with a pose that does not fully collapse the receptor binding cleft into an active-state conformation
details expand to inspect
full evidence table1 metrics
metricvaluetool
Ki 3478 nM GPCRDB/ChEMBL
structural qualityopenfold3
metricvaluenote
gpde0.990global PDE — lower = better
disorderNaNfraction disordered
3-letter notation
Tyr-Lys-Trp-Trp
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). Opioid receptor research tool (Ac-YKWW-NH₂ / CHEMBL102690) (pep-10413, v1). PeptideModel. https://peptidemodel.com/card/pep-10413
@peptide{pep10413,
  sequence = {YKWW},
  target   = {oprd1},
  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
discussion no comments
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peptidemodel.com CC-BY-SA-4.0 research only · not for human use