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 - DFBPOPIO0005(Opioid peptide)

DFBP ID	DFBPOPIO0005
Peptide sequence	YVPFPPF
Type	Native peptide
Peptide/Function name	Opioid peptide, Casoxin D

Function-activity relationship

Main bioactivity	Opioid activity
Otheir bioactivity	Vasoconstriction activity ^[D1], Multifunctional activity ^[D2]

Calculated physicochemical properties

Three-letter amino acid

Tyr-Val-Pro-Phe-Pro-Pro-Phe

Single-letter amino acid

YVPFPPF

Peptide length

Peptide mass

Experimental mass	Theoretical mass
N.D	866.02 Da ^c

Net charge

0.00 ^c

Isoelectric point (pI)

5.92 ^c

IC₅₀

N.D

pIC₅₀

N.D

GRAVY

0.5286^c

Hydrophilic residue ratio

85.71%^c

Peptide calculator

Peptide source & Food-borne protein(s) search

Classification	Human
Organism/Source	Human milk
Precursor protein	α_s1-Casein
Residue position	f(158-164)
Precursor protein(s) search	Source.1: DFBPPR7602 ---- Milk proteins ---- Alpha-S1-casein
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

The peptide Casoxin D has antiopioid and vasorelaxing activities which are mediated by the opioid μ-receptor and bradykinin B₁ receptors, respectively.) ^[4,5]

Table 1. Opoid activities of casoxin D derivatives
Peptides	Opioid activity (IC₅₀, μM)			Receptor assay (IC₅₀, μM)
Peptides	GPI	MVD	MVD/GPI	μ	δ	δ/μ
YVPFPPF (Casoxin D)	antagonist		－	250	150	0.6
YPFPPF	0.14	6.3	4.5	1.5	6.9	4.6
YPFPPW	0.08	10	125	0.31	3.5	11.3
YPFPPL	10	31	3.1	12.5	25	2.0
YPFPP-NH₂	1.0	15	15	13	55	4.2
YPFPP	0.30	9.2	30.7	4.3	27.5	6.1
YPFP-NH₂(Morphiceptin)	0.10	2.0	20	0.25	18.5	74

Specific target protein(s)

Specific Target Protein(s):
Mu-type opioid receptor
B1 bradykinin 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)N1[C@@]([H])(CCC1)C(=O)N[C@@]([H])(Cc1ccccc1)C(=O)O

Preparation method

Mode of preparation	Enzymatic hydrolysis
Enzyme(s)/starter culture	Human β-casein was hydrolyzed with pepsin-chymotrypsin.

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]	DFBPVACO0002
[D2]	DFBPMUFU0655

[D3]

[D4]

[D5]

[D6]

Reference(s)

Primary literature	Yoshikawa, M., Suganuma, H., Takahashi, M., Usui, H., Kurahashi, K., Chiba, H. Casomokinins, opioid/vaso-relaxing peptides derivatized from casoxin D or β-casomorphin-6. Regulatory Peptides. 1994, 53, S253-S4. DOI: 10.1016/0167-0115(94)90335-2
Other literature(s)	[1] Park Y W. Bioactive Components in Milk and Dairy Products[M]. 2009. [2] Teschemacher H. Opioid receptor ligands derived from food proteins.[J]. Current Pharmaceutical Design, 2003, 9(16):-. [3] Kostyra E, Sienkiewiczszłapka E, Jarmołowska B, et al. Opioid peptides derived from milk proteins.[J]. Polish Journal of Food & Nutrition Sciences, 2004. [4] Kato M , Fujiwara Y , Okamoto A , et al. Efficient Production of Casoxin D, a Bradykinin Agonist Peptide Derived from Human Casein, by Bacillus brevis[J]. Journal of the Agricultural Chemical Society of Japan, 1995, 59(11):4. [5] Fujita H , Suganuma H , Usui H , et al. Vasorelaxation by casomokinin L, a derivative of β-casomorphin and casoxin D, is mediated by NK1 receptor[J]. Peptides, 1996, 17(4):635-639. [6] Yoshikawa, M., Tani, F., Shiota, H., Suganuma, H., Usui, H., Kurahashi, K., and Chiba, H. 1994. Casoxin D, an opioid antagonist ileum-contract- ing/vasorelaxing peptide derived from human αs1-casein. In: β-Casomorphins and Related Pep- tides: Recent Developments. V. Brantl and H. Teschemacher, eds. VCH-Weinheim, Germany, pp. 43–48.
PubDate	1994