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 - DFBPOPIO0003(Opioid peptide)

DFBP ID	DFBPOPIO0003
Peptide sequence	YLLF
Type	Native peptide
Peptide/Function name	Opioid peptide, β-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-Leu-Leu-Phe

Single-letter amino acid

YLLF

Peptide length

Peptide mass

Experimental mass	Theoretical mass
N.D	554.67 Da ^c

Net charge

0.00 ^c

Isoelectric point (pI)

5.92 ^c

IC₅₀

N.D

pIC₅₀

N.D

GRAVY

2.2750^c

Hydrophilic residue ratio

75%^c

Peptide calculator

Peptide source & Food-borne protein(s) search

Classification	Animal
Organism/Source	Bovine milk protien
Precursor protein	β-Lactoglobulin
Residue position	f(102-105)^[3]
Precursor protein(s) search	Source.1: DFBPPR0115 ---- Milk proteins ---- Beta-lactoglobulin Source.2: DFBPPR1115 ---- Plant proteins ---- Jasmonoyl--L-amino acid synthetase GH3.3 Source.3: DFBPPR1175 ---- Plant proteins ---- Gibberellin 3-beta-dioxygenase 2 Source.4: DFBPPR1306 ---- Plant proteins ---- Two pore calcium channel protein 1 Source.5: DFBPPR1384 ---- Plant proteins ---- Oryzalexin E synthase Source.6: DFBPPR1832 ---- Plant proteins ---- ATP-dependent zinc metalloprotease FTSH 7, chloroplastic Source.7: DFBPPR1856 ---- Plant proteins ---- Aminopeptidase M1-D Source.8: DFBPPR1860 ---- Plant proteins ---- Kinesin-like protein KIN-7A Source.9: DFBPPR2171 ---- Plant proteins ---- Probable mixed-linked glucan synthase 8 Source.10: DFBPPR2456 ---- Plant proteins ---- Probable xyloglucan glycosyltransferase 9 Source.11: DFBPPR2535 ---- Plant proteins ---- Probable glucuronosyltransferase Os04g0650300 Source.12: DFBPPR2937 ---- Plant proteins ---- Probable xyloglucan glycosyltransferase 7 Source.13: DFBPPR2969 ---- Plant proteins ---- Probable xyloglucan glycosyltransferase 3 Source.14: DFBPPR3009 ---- Plant proteins ---- Probable xyloglucan glycosyltransferase 2 Source.15: DFBPPR3030 ---- Plant proteins ---- Ammonium transporter 1 member 3 Source.16: DFBPPR3136 ---- Plant proteins ---- Magnesium/proton exchanger 1 Source.17: DFBPPR3210 ---- Plant proteins ---- Ammonium transporter 1 member 2 Source.18: DFBPPR3281 ---- Plant proteins ---- Ammonium transporter 1 member 1 Source.19: DFBPPR3320 ---- Plant proteins ---- Probable xyloglucan glycosyltransferase 1 Source.20: DFBPPR3322 ---- Plant proteins ---- Putative xyloglucan glycosyltransferase 10 Source.21: DFBPPR3367 ---- Plant proteins ---- Probable phytol kinase 1, chloroplastic Source.22: DFBPPR3702 ---- Plant proteins ---- Probable indole-3-acetic acid-amido synthetase GH3.1 Source.23: DFBPPR3707 ---- Plant proteins ---- Probable indole-3-acetic acid-amido synthetase GH3.11 Source.24: DFBPPR3847 ---- Plant proteins ---- Probable indole-3-acetic acid-amido synthetase GH3.13 Source.25: DFBPPR3944 ---- Plant proteins ---- Magnesium/proton exchanger 2 Source.26: DFBPPR4176 ---- Plant proteins ---- 5'-adenylylsulfate reductase-like 3 Source.27: DFBPPR4772 ---- Plant proteins ---- SEC1 family transport protein SLY1 Source.28: DFBPPR5221 ---- Plant proteins ---- Protein TIC 214 Source.29: DFBPPR6148 ---- Plant proteins ---- Uncharacterized protein ycf70 Source.30: DFBPPR6670 ---- Plant proteins ---- Two pore calcium channel protein 1 Source.31: DFBPPR7117 ---- Plant proteins ---- Two pore calcium channel protein 1 Source.32: DFBPPR7652 ---- Milk proteins ---- Zinc transporter 4 Source.33: DFBPPR7687 ---- Milk proteins ---- Beta-lactoglobulin Source.34: DFBPPR7698 ---- Milk proteins ---- Beta-lactoglobulin-1/B Source.35: DFBPPR7714 ---- Milk proteins ---- Beta-lactoglobulin Source.36: DFBPPR8499 ---- Milk proteins ---- Beta-lactoglobulin Source.37: DFBPPR8507 ---- Milk proteins ---- Polycystin-2 Source.38: DFBPPR16197 ---- Animal proteins ---- Cytochrome c oxidase subunit 1 Source.39: DFBPPR16805 ---- Animal proteins ---- Dopamine beta-hydroxylase Source.40: DFBPPR16817 ---- Animal proteins ---- Cytochrome c oxidase subunit 1 Source.41: DFBPPR17366 ---- Animal proteins ---- Beta-adrenergic receptor kinase 1 Source.42: DFBPPR17452 ---- Animal proteins ---- CD81 antigen Source.43: DFBPPR17678 ---- Animal proteins ---- Ubiquitin carboxyl-terminal hydrolase 16 Source.44: DFBPPR17749 ---- Animal proteins ---- CD9 antigen Source.45: DFBPPR17811 ---- Animal proteins ---- YTH domain-containing family protein 2 Source.46: DFBPPR17890 ---- Animal proteins ---- Neuronal acetylcholine receptor subunit alpha-3 Source.47: DFBPPR17921 ---- Animal proteins ---- Ubiquitin carboxyl-terminal hydrolase 2 Source.48: DFBPPR17994 ---- Animal proteins ---- Lysophospholipid acyltransferase 7 Source.49: DFBPPR18000 ---- Animal proteins ---- Very-long-chain enoyl-CoA reductase Source.50: DFBPPR18002 ---- Animal proteins ---- Toll-like receptor 10 Source.51: DFBPPR18452 ---- Animal proteins ---- Ubiquitin carboxyl-terminal hydrolase 22 Source.52: DFBPPR18833 ---- Animal proteins ---- Ubiquitin carboxyl-terminal hydrolase 1 Source.53: DFBPPR18906 ---- Animal proteins ---- NADH dehydrogenase [ubiquinone] 1 alpha subcomplex subunit 9, mitochondrial Source.54: DFBPPR19730 ---- Animal proteins ---- Tensin-1 Source.55: DFBPPR19899 ---- Animal proteins ---- Receptor expression-enhancing protein 6 Source.56: DFBPPR19908 ---- Animal proteins ---- DNA replication licensing factor MCM6 Source.57: DFBPPR20470 ---- Animal proteins ---- Orexigenic neuropeptide QRFP Source.58: DFBPPR20650 ---- Animal proteins ---- WD repeat-containing protein 91 Source.59: DFBPPR20752 ---- Animal proteins ---- Tetraspanin-33 Source.60: DFBPPR20824 ---- Animal proteins ---- CD151 antigen Source.61: DFBPPR20999 ---- Animal proteins ---- Protein SERAC1 Source.62: DFBPPR21154 ---- Animal proteins ---- Proton-activated chloride channel Source.63: DFBPPR21410 ---- Animal proteins ---- Trans-2,3-enoyl-CoA reductase-like Source.64: DFBPPR22043 ---- Animal proteins ---- Leukocyte antigen CD37 Source.65: DFBPPR22444 ---- Animal proteins ---- Tetraspanin-11 Source.66: DFBPPR9072 ---- Animal proteins ---- CD9 antigen Source.67: DFBPPR9094 ---- Animal proteins ---- Aquaporin-5 Source.68: DFBPPR9703 ---- Animal proteins ---- Membrane-associated transporter protein Source.69: DFBPPR10046 ---- Animal proteins ---- Gallinacin-2 Source.70: DFBPPR10049 ---- Animal proteins ---- Transient receptor potential cation channel subfamily V member 4 Source.71: DFBPPR10224 ---- Animal proteins ---- Prolyl 3-hydroxylase 1 Source.72: DFBPPR10232 ---- Animal proteins ---- Neuronal acetylcholine receptor subunit alpha-4 Source.73: DFBPPR10335 ---- Animal proteins ---- RNA-binding protein with multiple splicing 2 Source.74: DFBPPR10360 ---- Animal proteins ---- Neuronal acetylcholine receptor subunit alpha-3 Source.75: DFBPPR10503 ---- Animal proteins ---- Follicle-stimulating hormone receptor Source.76: DFBPPR10519 ---- Animal proteins ---- Prolyl 3-hydroxylase 2 Source.77: DFBPPR10565 ---- Animal proteins ---- Acetylcholine receptor subunit delta Source.78: DFBPPR10617 ---- Animal proteins ---- Neuronal acetylcholine receptor subunit alpha-6 Source.79: DFBPPR10832 ---- Animal proteins ---- BMP/retinoic acid-inducible neural-specific protein 1 Source.80: DFBPPR10860 ---- Animal proteins ---- Ubiquitin carboxyl-terminal hydrolase 2 Source.81: DFBPPR10989 ---- Animal proteins ---- Neuronal acetylcholine receptor subunit alpha-2 Source.82: DFBPPR11001 ---- Animal proteins ---- Neuronal acetylcholine receptor subunit beta-3 Source.83: DFBPPR11135 ---- Animal proteins ---- Popeye domain-containing protein 3 Source.84: DFBPPR11142 ---- Animal proteins ---- Type I iodothyronine deiodinase Source.85: DFBPPR11212 ---- Animal proteins ---- Glycoprotein-N-acetylgalactosamine 3-beta-galactosyltransferase 1 Source.86: DFBPPR11438 ---- Animal proteins ---- NADH-ubiquinone oxidoreductase chain 4 Source.87: DFBPPR11573 ---- Animal proteins ---- tRNA-specific adenosine deaminase 1 Source.88: DFBPPR11698 ---- Animal proteins ---- NADH-cytochrome b5 reductase 2 Source.89: DFBPPR11804 ---- Animal proteins ---- WD repeat-containing protein 91 Source.90: DFBPPR12091 ---- Animal proteins ---- Neurofibromin Source.91: DFBPPR12180 ---- Animal proteins ---- Arylamine N-acetyltransferase, liver isozyme Source.92: DFBPPR12279 ---- Animal proteins ---- Phosphorylase b kinase regulatory subunit alpha, skeletal muscle isoform Source.93: DFBPPR12392 ---- Animal proteins ---- Large neutral amino acids transporter small subunit 2 Source.94: DFBPPR12550 ---- Animal proteins ---- Cytochrome c oxidase subunit 1 Source.95: DFBPPR13228 ---- Animal proteins ---- Cytochrome c oxidase subunit 1 Source.96: DFBPPR13444 ---- Animal proteins ---- Cytochrome c oxidase subunit 1 Source.97: DFBPPR13595 ---- Animal proteins ---- Cytochrome c oxidase subunit 1 Source.98: DFBPPR13819 ---- Animal proteins ---- Aquaporin-5 Source.99: DFBPPR15056 ---- Microorganism protein ---- RuvB-like helicase 2 Source.100: DFBPPR15144 ---- Microorganism protein ---- Palmitoyltransferase PFA4 Source.101: DFBPPR15275 ---- Microorganism protein ---- Exocyst complex protein EXO70 Source.102: DFBPPR15498 ---- Microorganism protein ---- Autophagy-related protein 22 Source.103: DFBPPR15662 ---- Microorganism protein ---- Nuclear rim protein 1 Source.104: DFBPPR8120 ---- Plant protein ---- Protein TIC 214 Source.105: DFBPPR8304 ---- Plant protein ---- Protein TIC 214
Link-research Inductive analysis	Link 1: DFBPOPIO0075----Bovine milk protien^[1]----β-Lactoglobulin

Biological/Functional activity & target protein

Opioid activity

The active form for the peptide YLLF was YLLF-NH₂ and showed weak opioid activity. It was specific ligands for the u-receptor ^[7], as shown in Table 1.

Table 1 Opioid activity of peptide
Peptide	IC₅₀ (uM)			Activity	References
	RA^a	GPI^b	MVD^c
YLLF-NH₂	160	160	> 1000	Opioid agonist	－
	－	－	－		[3]

^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)N[C@@]([H])(CC(C)C)C(=O)N[C@@]([H])(CC(C)C)C(=O)N[C@@]([H])(Cc1ccccc1)C(=O)O

Preparation method

Mode of preparation

Synthesis or Enzymatic hydrolysis^[2]

Enzyme(s)/starter culture

Peptide was synthesized by a solid-phase method on chloromethyl resin.

Hydrolysis with trypsin^[2].

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]	DFBPACEI0019, DFBPACEI1748
[D2]	DFBPMUFU0010

[D3]

[D4]

[D5]

[D6]

Reference(s)

Primary literature	Yoshikawa, M., Tani, F., Yoshimura, T., Chiba, H. Opioid Peptides from Milk Proteins. Agricultural and Biological Chemistry. 2014, 50, 2419-21. DOI: 10.1080/00021369.1986.10867763
Other literature(s)	[1] Park Y W. Bioactive Components in Milk and Dairy Products[M]. 2009. [2] Mullally M M, Meisel H, Fitzgerald R J. Synthetic peptides corresponding to alpha-lactalbumin and beta-lactoglobulin sequences with angiotensin-I-converting enzyme inhibitory activity[J]. Biol Chem Hoppe Seyler, 1996, 377(4):259-260. [3] Kostyra E, Sienkiewiczszłapka E, Jarmołowska B, et al. Opioid peptides derived from milk proteins.[J]. Polish Journal of Food & Nutrition Sciences, 2004. [4] Tani F., Iio K., Chiba H., Yoshikawa M., Isolation and characterization of opioid antagonist peptides derived from human lactoferrin. Agr. Biol. Chem., 1990, 54, 1803–1810. [5] Meisel H. Overview on Milk Protein-derived Peptides[J]. International Dairy Journal, 1998, 8(5–6):363-373. [6] Schlimme E, Meisel H. Bioactive peptides derived from milk proteins. Structural, physiological and analytical aspects.[J]. Nahrung, 1995, 39(1):1-20. [7] Teschemacher, H., Opioid receptor ligands derived from food proteins. Curr Pharm Des, 2003. 9(16): p. 1331-44.
PubDate	2014