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 - DFBPDPIV0142(DPP IV-inhibitory peptide)

DFBP ID	DFBPDPIV0142
Peptide sequence	VRGP
Type	Native peptide
Peptide/Function name	DPP-IV inhibitory peptide, Anti-diabetic peptide

Function-activity relationship

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

Calculated physicochemical properties

Three-letter amino acid

Val-Arg-Gly-Pro

Single-letter amino acid

VRGP

Peptide length

Peptide mass

Experimental mass	Theoretical mass
N.D	427.50 Da ^c

Net charge

0.00 ^c

Isoelectric point (pI)

11.04 ^c

IC₅₀

N.D

pIC₅₀

N.D

GRAVY

-0.5750^c

Hydrophilic residue ratio

75%^c

Peptide calculator

Peptide source & Food-borne protein(s) search

Classification	Animal
Organism/Source	Bovine milk protein
Precursor protein	β-Casein
Residue position	f(201-204)
Precursor protein(s) search	Source.1: DFBPPR1175 ---- Plant proteins ---- Gibberellin 3-beta-dioxygenase 2 Source.2: DFBPPR1228 ---- Plant proteins ---- Isoamylase 2, chloroplastic Source.3: DFBPPR1281 ---- Plant proteins ---- Arsenate reductase 2.2 Source.4: DFBPPR1283 ---- Plant proteins ---- Arsenate reductase 2.1 Source.5: DFBPPR1693 ---- Plant proteins ---- Cytochrome P450 734A4 Source.6: DFBPPR1694 ---- Plant proteins ---- Cytochrome P450 734A2 Source.7: DFBPPR1971 ---- Plant proteins ---- Protein disulfide isomerase-like 1-3 Source.8: DFBPPR2615 ---- Plant proteins ---- Cytochrome P450 734A5 Source.9: DFBPPR2758 ---- Plant proteins ---- Expansin-B17 Source.10: DFBPPR2843 ---- Plant proteins ---- Probable aldehyde oxidase 2 Source.11: DFBPPR2905 ---- Plant proteins ---- Cytochrome P450 714C2 Source.12: DFBPPR2927 ---- Plant proteins ---- Probable aldehyde oxidase 3 Source.13: DFBPPR3148 ---- Plant proteins ---- Growth-regulating factor 8 Source.14: DFBPPR3290 ---- Plant proteins ---- Transport inhibitor response 1-like protein Os05g0150500 Source.15: DFBPPR3373 ---- Plant proteins ---- 4-coumarate--CoA ligase-like 1 Source.16: DFBPPR3519 ---- Plant proteins ---- Growth-regulating factor 6 Source.17: DFBPPR3602 ---- Plant proteins ---- Coatomer subunit alpha-2 Source.18: DFBPPR3822 ---- Plant proteins ---- Coatomer subunit alpha-3 Source.19: DFBPPR3840 ---- Plant proteins ---- Growth-regulating factor 7 Source.20: DFBPPR3928 ---- Plant proteins ---- Coatomer subunit alpha-1 Source.21: DFBPPR3937 ---- Plant proteins ---- Zinc-finger homeodomain protein 10 Source.22: DFBPPR3976 ---- Plant proteins ---- Double-stranded RNA-binding protein 4 Source.23: DFBPPR3980 ---- Plant proteins ---- 4-coumarate--CoA ligase-like 7 Source.24: DFBPPR4121 ---- Plant proteins ---- Protein argonaute 1C Source.25: DFBPPR4264 ---- Plant proteins ---- Putative 4-coumarate--CoA ligase-like 8 Source.26: DFBPPR4930 ---- Plant proteins ---- Cytochrome b6-f complex iron-sulfur subunit, chloroplastic Source.27: DFBPPR5400 ---- Plant proteins ---- Indole-3-acetaldehyde oxidase Source.28: DFBPPR5445 ---- Plant proteins ---- Bifunctional aspartokinase/homoserine dehydrogenase 2, chloroplastic Source.29: DFBPPR5447 ---- Plant proteins ---- Bifunctional aspartokinase/homoserine dehydrogenase 1, chloroplastic Source.30: DFBPPR5579 ---- Plant proteins ---- Indole-3-acetaldehyde oxidase Source.31: DFBPPR6321 ---- Plant proteins ---- Cytochrome b6-f complex iron-sulfur subunit, chloroplastic Source.32: DFBPPR6554 ---- Plant proteins ---- Retinoblastoma-related protein 1 Source.33: DFBPPR6555 ---- Plant proteins ---- Retinoblastoma-related protein 1 Source.34: DFBPPR6666 ---- Plant proteins ---- Cytochrome b6-f complex iron-sulfur subunit, chloroplastic Source.35: DFBPPR7596 ---- Milk proteins ---- Lactotransferrin Source.36: DFBPPR7658 ---- Milk proteins ---- Lactotransferrin Source.37: DFBPPR7669 ---- Milk proteins ---- Lactotransferrin Source.38: DFBPPR7692 ---- Milk proteins ---- Beta-casein Source.39: DFBPPR7700 ---- Milk proteins ---- Beta-casein Source.40: DFBPPR7718 ---- Milk proteins ---- Beta-casein Source.41: DFBPPR8489 ---- Milk proteins ---- Beta-casein Source.42: DFBPPR16284 ---- Animal proteins ---- Collagen alpha-2(I) chain Source.43: DFBPPR16580 ---- Animal proteins ---- Fibrinogen alpha chain Source.44: DFBPPR16814 ---- Animal proteins ---- Prothrombin Source.45: DFBPPR16847 ---- Animal proteins ---- Fibrinogen alpha chain Source.46: DFBPPR16968 ---- Animal proteins ---- Inhibitor of nuclear factor kappa-B kinase subunit beta Source.47: DFBPPR17088 ---- Animal proteins ---- Collagen alpha-2(I) chain Source.48: DFBPPR17262 ---- Animal proteins ---- Ubiquitin carboxyl-terminal hydrolase 33 Source.49: DFBPPR17267 ---- Animal proteins ---- Vacuolar protein sorting-associated protein 4B Source.50: DFBPPR17296 ---- Animal proteins ---- Dynamin-2 Source.51: DFBPPR17324 ---- Animal proteins ---- Prostaglandin-H2 D-isomerase Source.52: DFBPPR17450 ---- Animal proteins ---- Adhesion G protein-coupled receptor L3 Source.53: DFBPPR18473 ---- Animal proteins ---- Sharpin Source.54: DFBPPR18732 ---- Animal proteins ---- RNA-binding protein 8A Source.55: DFBPPR18787 ---- Animal proteins ---- Rho-related GTP-binding protein RhoU Source.56: DFBPPR19075 ---- Animal proteins ---- Ubiquitin-conjugating enzyme E2 J2 Source.57: DFBPPR19182 ---- Animal proteins ---- Protoporphyrinogen oxidase Source.58: DFBPPR19357 ---- Animal proteins ---- Collagen alpha-2(IX) chain Source.59: DFBPPR19388 ---- Animal proteins ---- Deoxyhypusine hydroxylase Source.60: DFBPPR19541 ---- Animal proteins ---- Serrate RNA effector molecule homolog Source.61: DFBPPR19580 ---- Animal proteins ---- Endosomal/lysosomal potassium channel TMEM175 Source.62: DFBPPR19710 ---- Animal proteins ---- Beta-galactosidase Source.63: DFBPPR19823 ---- Animal proteins ---- Alanine aminotransferase 1 Source.64: DFBPPR19833 ---- Animal proteins ---- Contactin-1 Source.65: DFBPPR19959 ---- Animal proteins ---- Complement C1q subcomponent subunit B Source.66: DFBPPR20229 ---- Animal proteins ---- N-acetylglucosamine-6-sulfatase Source.67: DFBPPR20275 ---- Animal proteins ---- Malonate--CoA ligase ACSF3, mitochondrial Source.68: DFBPPR20560 ---- Animal proteins ---- Draxin Source.69: DFBPPR20587 ---- Animal proteins ---- Nicotinate-nucleotide pyrophosphorylase [carboxylating] Source.70: DFBPPR21008 ---- Animal proteins ---- Gamma-glutamylaminecyclotransferase Source.71: DFBPPR21100 ---- Animal proteins ---- Cochlin Source.72: DFBPPR21154 ---- Animal proteins ---- Proton-activated chloride channel Source.73: DFBPPR21168 ---- Animal proteins ---- Pyruvate dehydrogenase phosphatase regulatory subunit, mitochondrial Source.74: DFBPPR22449 ---- Animal proteins ---- Complement C1q and tumor necrosis factor-related protein 9 Source.75: DFBPPR22478 ---- Animal proteins ---- Trichohyalin-like protein 1 Source.76: DFBPPR22655 ---- Animal proteins ---- Coiled-coil domain-containing protein 190 Source.77: DFBPPR22680 ---- Animal proteins ---- Proline-rich protein 32 Source.78: DFBPPR9032 ---- Animal proteins ---- NADP-dependent malic enzyme Source.79: DFBPPR9543 ---- Animal proteins ---- Beta-glucuronidase Source.80: DFBPPR10119 ---- Animal proteins ---- Down syndrome cell adhesion molecule homolog Source.81: DFBPPR10162 ---- Animal proteins ---- Dynamin-like 120 kDa protein, mitochondrial Source.82: DFBPPR10355 ---- Animal proteins ---- Down syndrome cell adhesion molecule-like protein 1 homolog Source.83: DFBPPR10445 ---- Animal proteins ---- Collagen alpha-1(XVII) chain Source.84: DFBPPR10458 ---- Animal proteins ---- Neurofascin Source.85: DFBPPR10630 ---- Animal proteins ---- Contactin-2 Source.86: DFBPPR10653 ---- Animal proteins ---- Contactin-1 Source.87: DFBPPR10736 ---- Animal proteins ---- Katanin p60 ATPase-containing subunit A1 Source.88: DFBPPR10820 ---- Animal proteins ---- Collagen alpha-1(IX) chain Source.89: DFBPPR10896 ---- Animal proteins ---- Contactin-5 Source.90: DFBPPR11014 ---- Animal proteins ---- NEDD8-conjugating enzyme UBE2F Source.91: DFBPPR11133 ---- Animal proteins ---- Transcription factor MafG Source.92: DFBPPR11511 ---- Animal proteins ---- E3 ubiquitin-protein ligase MIB2 Source.93: DFBPPR11629 ---- Animal proteins ---- THO complex subunit 5 homolog Source.94: DFBPPR11635 ---- Animal proteins ---- Cochlin Source.95: DFBPPR13478 ---- Animal proteins ---- Inter-alpha-trypsin inhibitor Source.96: DFBPPR13482 ---- Animal proteins ---- N-acetylglucosamine-6-sulfatase Source.97: DFBPPR13620 ---- Animal proteins ---- Prostaglandin-H2 D-isomerase Source.98: DFBPPR13621 ---- Animal proteins ---- Amiloride-sensitive sodium channel subunit beta Source.99: DFBPPR13855 ---- Animal proteins ---- Inter-alpha-trypsin inhibitor Source.100: DFBPPR14127 ---- Marine protein ---- RNA-binding protein 8A Source.101: DFBPPR14240 ---- Marine protein ---- Otolin-1 Source.102: DFBPPR14633 ---- Marine protein ---- Keratin, type I cytoskeletal 18 Source.103: DFBPPR14660 ---- Marine protein ---- Otolin-1 Source.104: DFBPPR15113 ---- Microorganism protein ---- NADH-cytochrome b5 reductase 1 Source.105: DFBPPR7786 ---- Plant protein ---- tRNA (guanine(37)-N1)-methyltransferase Source.106: DFBPPR8253 ---- Plant protein ---- DNA-directed RNA polymerase subunit alpha
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

DPP IV-inhibitory activity

The peptide showed low Dipeptidyl Peptidase IV (EC 3.4.14.5) inhibitory activity with the IC₅₀ values of > 3000 μM. Comapred with other peptides, as shown in table1.

Table 1 IC₅₀ (μM) values of synthetic peptides against DPP-IV activity and the type of inhibition.
Peptides	DPP-IV IC₅₀ (μM)	Type of inhibition
IPI	3.5 ± 0.2	Competitive
FLQP	65.3 ± 3.5	Competitive
IP	149.6 ± 6.1	Competitive
WIQP	237.3 ± 1.3	Non-competitive
VLGP	580.4 ± 11.3	Competitive
YP	658.1 ± 8.0	Competitive
LP	712.5 ± 11.0	Competitive
VR	826.1 ± 30.1	Non-competitive
VRGP	> 3000	Not determined
QP	> 4000	Not determined
IQP	> 4000	Not determined
NP	> 20000	Not determined
GP	-	Not applicable
HQP	-	Not applicable
ITP	-	Not applicable
KHP	-	Not applicable
KYP	-	Not applicable
NSLP	-	Not applicable
VEP	-	Not applicable

Specific target protein(s)

Specific Target Protein(s):
Dipeptidyl peptidase 4

Taste properties & Structure

Bitterness

Literature report	N.D
Bitter prediction tools	Non-bitter taste ^prediction

SMILES

N[C@@]([H])(C(C)C)C(=O)N[C@@]([H])(CCCNC(=N)N)C(=O)NCC(=O)N1[C@@]([H])(CCC1)C(=O)O

Preparation method

Mode of preparation	Enzymatic hydrolysis
Enzyme(s)/starter culture	The β-casein were digested in silico with a prolyl oligopeptidase (EC 3.4.21.26) activity to release peptides with a Pro residue at the C terminus.

Stability & Cytotoxicity

Peptide stability

Literature report:

In silico digestion with gastrointestinal enzyme activities was subsequently carried out on the eight casein-derived peptides which inhibited DPP-IV. Of the eight DPP-IV inhibitory peptides studied herein, two (Asn-Pro and Ile-Pro) could not theoretically be further cleaved by pepsin, trypsin and chymotrypsin. Six (Tyr-Pro, Leu-Pro, Trp-Ile-Gln-Pro, Val- Leu-Gly-Pro, Phe-Leu-Gln-Pro and Val-Arg-Gly-Pro) were theoretically cleaved. Apart from Gly-Pro, which was predicted to be released by chymotryptic action on Val-Leu-Gly-Pro and the tryptic action of Val-Arg-Gly-Pro, all the other breakdown peptides (Val-Arg, Ile-Gln-Pro and Gln-Pro) were DPP-IV inhibitors. However, these were not potent DPP-IV inhibitors as their IC₅₀ values ranged from 826.1 ± 30.1 to > 4000 μM (Table 1). Trp and Leu, which were predicted to be released from four peptides (Leu-Pro, Trp-Ile-Gln-Pro, Val-Leu-Gly-Pro and Phe-Leu-Gln-Pro), have previously been identified as weak DPP-IV inhibitors with IC₅₀ values of 4280 ± 48 and 3419 ± 56 μM, respectively.

EHP-Tool:

Enzymatic Hydrolysis Prediction Tool (EHP-Tool)

Peptide cytotoxicity

Literature report:	N.D
Prediction:	ToxinPred

Additional information

This peptide was obtained by a prolyl oligopeptidase (EC 3.4.21.26) digestion in silico, and it was not verified whether the peptide could be efficiently released by the enzyme.

Database cross-references

DFBP

[D1]	DFBPACEI0055
[D2]	DFBPMUFU0029

[D3]

[D4]

[D5]

[D6]

Reference(s)

Primary literature	Nongonierma, A.B., FitzGerald, R.J. Inhibition of dipeptidyl peptidase IV (DPP-IV) by proline containing casein-derived peptides. Journal of Functional Foods. 2013, 5, 1909-17. DOI: 10.1016/j.jff.2013.09.012
Other literature(s)	N.D
PubDate	2013