Peptide properties

1Top 2Function-activity relationship 3Calculated physicochemical properties 4Peptide source & Food-borne protein(s) search 5Biological/Functional activity & target protein 6Taste properties & Structure 7Preparation method 8Stability & Cytotoxicity 9Additional information 10Database cross-references 11Reference(s)

List of peptide properties

DFBP ID - DFBPOPIO0038(Opioid peptide)

DFBP ID	DFBPOPIO0038
Peptide sequence	YVPFP
Type	Native peptide
Peptide/Function name	Opioid peptide, a_s1-Casomorphin

Function-activity relationship

Main bioactivity	Opioid activity
Otheir bioactivity	Anticancer activity ^[D1]

Calculated physicochemical properties

Three-letter amino acid

Tyr-Val-Pro-Phe-Pro

Single-letter amino acid

YVPFP

Peptide length

Peptide mass

Experimental mass	Theoretical mass
N.D	621.73 Da ^c

Net charge

0.00 ^c

Isoelectric point (pI)

5.92 ^c

IC₅₀

N.D

pIC₅₀

N.D

GRAVY

0.5000^c

Hydrophilic residue ratio

80%^c

Peptide calculator

Peptide source & Food-borne protein(s) search

Classification	Human
Organism/Source	Human milk
Precursor protein	α_s1-Casein
Residue position	f(158-162)
Precursor protein(s) search	Source.1: DFBPPR1946 ---- Plant proteins ---- Phytochrome A Source.2: DFBPPR5615 ---- Plant proteins ---- Regulatory protein viviparous-1 Source.3: DFBPPR5698 ---- Plant proteins ---- Phytochrome A Source.4: DFBPPR7602 ---- Milk proteins ---- Alpha-S1-casein Source.5: DFBPPR7723 ---- Plant proteins ---- Phytochrome A type 3 Source.6: DFBPPR7726 ---- Plant proteins ---- Phytochrome A type 4 Source.7: DFBPPR7727 ---- Plant proteins ---- Phytochrome A type 5 Source.8: DFBPPR22754 ---- Animal proteins ---- Uncharacterized protein C1orf158 homolog Source.9: DFBPPR7814 ---- Plant protein ---- Phytochrome a
Link-research Inductive analysis	There are no literature reports on the discovery of this sequence in other food-source proteins.

Biological/Functional activity & target protein

Opioid activity

α_s1-Casomorphin was found to bind with high affinity to all three subtypes of the κ-opioid receptor (κ₁-κ₃). When amidated at the C-terminus, α_s1-casomorphin amide binds to the δ- and κ₃-opioid sites. Both α_s1-casomorphin and its amide inhibit in a dose- dependent and reversible manner the proliferation of T47D human breast cancer cells. This anti-proliferative activity was greater for α_s1-casomorphin, which was the most potent opioid in inhibiting T47D cell proliferation, as shown in table 1.

Table 1 Affinity of α_s1-casomorphin and α_s1-casomorphin amide for opioid binding sites in T47D human breastcells and rat brain membranes
Ligand		Affinity (nM)
Ligand		Effector	αs1-Casomorphin	αs1-Casomorphin amide	Detected opioid sites
T47D cells	[³H]Ethylketocyclazocine	－	0.1	> 1000	ξ, κ₁, κ₂
	[³H]Ethylketocyclazocine	10 μM DADLE	0.7	> 1000	κ₁
	[³H]Diprenorphine	－	0.5	0.12	ξ, κ₂, κ₃
	[³H]Diprenorphine	10 μM DADLE	0.006	0.2	κ₃
	[³H]DPDPE	－	> 1000	1.7	δ
Rat brain membranes	[³H]DSLET	－	2600	> 10000	δ
Rat brain membranes	[³H]DAGO	－	> 10000	1000	μ

Opioid agonist/antagonist, μ / δ <<< κ ^[1].

Specific target protein(s)

Specific Target Protein(s):
Kappa-type opioid receptor
Delta-type opioid receptor

Taste properties & Structure

Bitterness

Literature report	N.D
Bitter prediction tools	Bitter taste ^prediction

SMILES

N[C@@]([H])(Cc1ccc(O)cc1)C(=O)N[C@@]([H])(C(C)C)C(=O)N1[C@@]([H])(CCC1)C(=O)N[C@@]([H])(Cc1ccccc1)C(=O)N1[C@@]([H])(CCC1)C(=O)O

Preparation method

Mode of preparation	Synthesis peptide
Enzyme(s)/starter culture	The peptide was synthesized by conventional peptide chemistry methods.

Stability & Cytotoxicity

Peptide stability

Literature report:	N.D
EHP-Tool:	Enzymatic Hydrolysis Prediction Tool (EHP-Tool)

Peptide cytotoxicity

Literature report:	N.D
Prediction:	ToxinPred

Additional information

N.D

Database cross-references

DFBP

[D1]	DFBPANCA0651

[D2]

[D3]

[D4]

[D5]

Reference(s)

Primary literature	Kampa M, Loukas S, Hatzoglou A, Martin P, Martin PM, Castanas E. Identification of a novel opioid peptide (Tyr-Val-Pro-Phe-Pro) derived from human alpha S1 casein (alpha S1-casomorphin, and alpha S1-casomorphin amide). Biochem J. 1996 Nov 1;319 ( Pt 3)(Pt 3):903-8. PMID: 8920997 DOI: 10.1042/bj3190903
Other literature(s)	[1] Teschemacher H. Opioid receptor ligands derived from food proteins.[J]. Current Pharmaceutical Design, 2003, 9(16):-.
PubDate	1996