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 - DFBPOPIO0078(Opioid peptide)

DFBP ID	DFBPOPIO0078
Peptide sequence	YGLF
Type	Native peptide
Peptide/Function name	Opioid peptide, α-Lactorphin

Function-activity relationship

Main bioactivity	Opioid activity
Otheir bioactivity	ACE-inhibitory activity ^[D1], Multifunctional activity ^[D2]

Calculated physicochemical properties

Three-letter amino acid

Tyr-Gly-Leu-Phe

Single-letter amino acid

YGLF

Peptide length

Peptide mass

Experimental mass	Theoretical mass
N.D	498.57 Da ^c

Net charge

0.00 ^c

Isoelectric point (pI)

5.92 ^c

IC₅₀

N.D

pIC₅₀

N.D

GRAVY

1.2250^c

Hydrophilic residue ratio

75%^c

Peptide calculator

Peptide source & Food-borne protein(s) search

Classification	Animal
Organism/Source	Bovine milk protein^[1]
Precursor protein	α-Lactalbumin
Residue position	f(50-53)
Precursor protein(s) search	Source.1: DFBPPR0858 ---- Plant proteins ---- Bidirectional sugar transporter SWEET11 Source.2: DFBPPR0884 ---- Plant proteins ---- Chitin elicitor receptor kinase 1 Source.3: DFBPPR0951 ---- Plant proteins ---- Calpain-type cysteine protease ADL1 Source.4: DFBPPR0990 ---- Plant proteins ---- LysM domain receptor-like kinase 10 Source.5: DFBPPR1031 ---- Plant proteins ---- Transcription factor EAT1 Source.6: DFBPPR1535 ---- Plant proteins ---- Photosystem I P700 chlorophyll a apoprotein A1 Source.7: DFBPPR1949 ---- Plant proteins ---- Beta-glucosidase-like SFR2, chloroplastic Source.8: DFBPPR2246 ---- Plant proteins ---- Probable DNA helicase MCM9 Source.9: DFBPPR2478 ---- Plant proteins ---- NAD(P)H-quinone oxidoreductase subunit 1, chloroplastic Source.10: DFBPPR3030 ---- Plant proteins ---- Ammonium transporter 1 member 3 Source.11: DFBPPR3077 ---- Plant proteins ---- ABC transporter G family member 31 Source.12: DFBPPR3210 ---- Plant proteins ---- Ammonium transporter 1 member 2 Source.13: DFBPPR3281 ---- Plant proteins ---- Ammonium transporter 1 member 1 Source.14: DFBPPR3410 ---- Plant proteins ---- Probable inorganic phosphate transporter 1-5 Source.15: DFBPPR3423 ---- Plant proteins ---- ABC transporter G family member 40 Source.16: DFBPPR3572 ---- Plant proteins ---- Probable inorganic phosphate transporter 1-9 Source.17: DFBPPR3592 ---- Plant proteins ---- Probable inorganic phosphate transporter 1-12 Source.18: DFBPPR3897 ---- Plant proteins ---- Putative inorganic phosphate transporter 1-13 Source.19: DFBPPR5047 ---- Plant proteins ---- Photosystem I P700 chlorophyll a apoprotein A1 Source.20: DFBPPR5184 ---- Plant proteins ---- Omega-6 fatty acid desaturase, endoplasmic reticulum isozyme 2 Source.21: DFBPPR5563 ---- Plant proteins ---- Photosystem I P700 chlorophyll a apoprotein A1 Source.22: DFBPPR5671 ---- Plant proteins ---- NAD(P)H-quinone oxidoreductase subunit 1, chloroplastic Source.23: DFBPPR6260 ---- Plant proteins ---- Delta(24)-sterol reductase Source.24: DFBPPR6274 ---- Plant proteins ---- Photosystem I P700 chlorophyll a apoprotein A1 Source.25: DFBPPR6696 ---- Plant proteins ---- Photosystem I P700 chlorophyll a apoprotein A1 Source.26: DFBPPR6780 ---- Plant proteins ---- NAD(P)H-quinone oxidoreductase subunit 1, chloroplastic Source.27: DFBPPR6861 ---- Plant proteins ---- Alpha-glucan phosphorylase, H isozyme Source.28: DFBPPR7065 ---- Plant proteins ---- Photosystem I P700 chlorophyll a apoprotein A1 Source.29: DFBPPR7082 ---- Plant proteins ---- NAD(P)H-quinone oxidoreductase subunit 1, chloroplastic Source.30: DFBPPR7597 ---- Milk proteins ---- Alpha-lactalbumin Source.31: DFBPPR7660 ---- Milk proteins ---- Alpha-lactalbumin Source.32: DFBPPR7667 ---- Milk proteins ---- Lysozyme C, milk isozyme Source.33: DFBPPR7670 ---- Milk proteins ---- Alpha-lactalbumin B/C Source.34: DFBPPR7671 ---- Milk proteins ---- Alpha-lactalbumin A Source.35: DFBPPR7685 ---- Milk proteins ---- Alpha-lactalbumin Source.36: DFBPPR7697 ---- Milk proteins ---- Alpha-lactalbumin Source.37: DFBPPR7711 ---- Milk proteins ---- Alpha-lactalbumin Source.38: DFBPPR8490 ---- Milk proteins ---- Alpha-lactalbumin Source.39: DFBPPR16031 ---- Animal proteins ---- DNA-dependent protein kinase catalytic subunit Source.40: DFBPPR16455 ---- Animal proteins ---- Substance-P receptor Source.41: DFBPPR16622 ---- Animal proteins ---- EGF domain-specific O-linked N-acetylglucosamine transferase Source.42: DFBPPR18026 ---- Animal proteins ---- Triokinase/FMN cyclase Source.43: DFBPPR18833 ---- Animal proteins ---- Ubiquitin carboxyl-terminal hydrolase 1 Source.44: DFBPPR19258 ---- Animal proteins ---- Cytochrome P450 3A28 Source.45: DFBPPR19394 ---- Animal proteins ---- Solute carrier family 10 member 6 Source.46: DFBPPR19608 ---- Animal proteins ---- Anoctamin-4 Source.47: DFBPPR19609 ---- Animal proteins ---- Chemokine C-C motif receptor-like 2 Source.48: DFBPPR19819 ---- Animal proteins ---- Heat shock protein 75 kDa, mitochondrial Source.49: DFBPPR19899 ---- Animal proteins ---- Receptor expression-enhancing protein 6 Source.50: DFBPPR20270 ---- Animal proteins ---- EGF domain-specific O-linked N-acetylglucosamine transferase Source.51: DFBPPR20279 ---- Animal proteins ---- Lysozyme-like protein 4 Source.52: DFBPPR21370 ---- Animal proteins ---- Lipase maturation factor 2 Source.53: DFBPPR21386 ---- Animal proteins ---- Protein phosphatase 1 regulatory subunit 3B Source.54: DFBPPR21600 ---- Animal proteins ---- Phosphatidylinositol N-acetylglucosaminyltransferase subunit H Source.55: DFBPPR22088 ---- Animal proteins ---- Protein YIPF7 Source.56: DFBPPR22472 ---- Animal proteins ---- Aldehyde dehydrogenase family 16 member A1 Source.57: DFBPPR8554 ---- Animal proteins ---- Glutamate carboxypeptidase 2 Source.58: DFBPPR8614 ---- Animal proteins ---- Triokinase/FMN cyclase Source.59: DFBPPR9541 ---- Animal proteins ---- Choline O-acetyltransferase Source.60: DFBPPR10075 ---- Animal proteins ---- Mast/stem cell growth factor receptor Kit Source.61: DFBPPR10191 ---- Animal proteins ---- Src substrate protein p85 Source.62: DFBPPR10411 ---- Animal proteins ---- DNA-dependent protein kinase catalytic subunit Source.63: DFBPPR10476 ---- Animal proteins ---- CAP-Gly domain-containing linker protein 1 Source.64: DFBPPR11385 ---- Animal proteins ---- EGF domain-specific O-linked N-acetylglucosamine transferase Source.65: DFBPPR11555 ---- Animal proteins ---- Choline O-acetyltransferase Source.66: DFBPPR11735 ---- Animal proteins ---- Protein YIPF3 Source.67: DFBPPR12020 ---- Animal proteins ---- Lipase maturation factor 2 Source.68: DFBPPR12294 ---- Animal proteins ---- Zona pellucida sperm-binding protein 3 Source.69: DFBPPR13206 ---- Animal proteins ---- Retinal dehydrogenase 1 Source.70: DFBPPR14006 ---- Animal proteins ---- Acyl-CoA desaturase Source.71: DFBPPR14204 ---- Marine protein ---- Riboflavin transporter 2 Source.72: DFBPPR14477 ---- Marine protein ---- 30S ribosomal protein S1, chloroplastic Source.73: DFBPPR14522 ---- Marine protein ---- Uncharacterized protein ycf20 Source.74: DFBPPR15820 ---- Microorganism protein ---- 6-phospho-beta-galactosidase Source.75: DFBPPR7772 ---- Plant protein ---- Photosystem I P700 chlorophyll a apoprotein A1 Source.76: DFBPPR7804 ---- Plant protein ---- NAD(P)H-quinone oxidoreductase subunit 1, chloroplastic Source.77: DFBPPR7932 ---- Plant protein ---- Alpha-1,4 glucan phosphorylase L isozyme, chloroplastic/amyloplastic Source.78: DFBPPR7937 ---- Plant protein ---- Alpha-glucan phosphorylase, H isozyme Source.79: DFBPPR7992 ---- Plant protein ---- Photosystem I P700 chlorophyll a apoprotein A1 Source.80: DFBPPR8044 ---- Plant protein ---- Photosystem I P700 chlorophyll a apoprotein A1 Source.81: DFBPPR8224 ---- Plant protein ---- Photosystem I P700 chlorophyll a apoprotein A1
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

This peptide behave as μ-type ligand opioid agoinst with low potency (IC₅₀ = 67.0 umol/l) ^[1].
YGLF-NH₂ showed weak opioid activity for μ-opiate receptor. As shown in table 1.

Table 1 Opioid activity of peptides
Peptide	IC₅₀ (uM)			Activity	References
	RA^a	GPI^b	MVD^c
YGLF-NH₂	300	50	> 1000	Opioid agonist	[3]
	－	－	－		[4]

^a Radioreceptor assay in the presence of 1 nM [³H]naloxone.
^b Guinea pig ileum assay.
^c Mouse vas deferens assay.

Specific target protein(s)

Specific Target Protein(s):
Mu-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)NCC(=O)N[C@@]([H])(CC(C)C)C(=O)N[C@@]([H])(Cc1ccccc1)C(=O)O

Preparation method

Mode of preparation	Synthesis
Enzyme(s)/starter culture	Peptide was synthesized by a solid-phase method on chloromethyl resin.

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

The peptide was also found in human milk protein: α-Lactalbumin, f(50-53) ^[5].

Database cross-references

DFBP

[D1]	DFBPACEI0020
[D2]	DFBPMUFU0011

[D3]

[D4]

[D5]

[D6]

Reference(s)

Primary literature	Antila, P., Paakkari, I., Järvinen, A., Mattila, M.J., Laukkanen, M., Pihlanto-Leppälä, A., et al. Opioid peptides derived from in-vitro proteolysis of bovine whey proteins. International Dairy Journal. 1991, 1, 215-29. DOI: 10.1016/0958-6946(91)90015-Z
Other literature(s)	[1] Meisel H, Fitzgerald R J. Opioid peptides encrypted in intact milk protein sequences.[J]. British Journal of Nutrition, 2000, 84(S1):27-31. [2] Schlimme E, Meisel H. Bioactive peptides derived from milk proteins. Structural, physiological and analytical aspects.[J]. Nahrung, 1995, 39(1):1-20. [3] Yoshikawa, M., Tani, F., Yoshimura, T., Chiba, H. Opioid Peptides from Milk Proteins. Agricultural and Biological Chemistry. 2014, 50, 2419-21. [4] Kostyra E, Sienkiewiczszłapka E, Jarmołowska B, et al. Opioid peptides derived from milk proteins.[J]. Polish Journal of Food & Nutrition Sciences, 2004. [5] Meisel H, Fitzgerald R J. Opioid peptides encrypted in intact milk protein sequences.[J]. British Journal of Nutrition, 2000, 84(S1):27-31. [6] Meisel, H. Overview on Milk Protein-derived Peptides. International Dairy Journal. 1998, 8, 363-73.
PubDate	1991