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 - DFBPOPIO0017(Opioid peptide)

DFBP ID	DFBPOPIO0017
Peptide sequence	VVYPWTQ
Type	Native peptide
Peptide/Function name	Opioid peptide, VV-hemorphin-5, Valorphin^[6]

Function-activity relationship

Main bioactivity	Opioid activity
Otheir bioactivity	ACE-inhibitory activity ^[D1], DPP IV-inhibitory activity ^[D2], Multifunctional activity ^[D3]

Calculated physicochemical properties

Three-letter amino acid

Val-Val-Tyr-Pro-Trp-Thr-Gln

Single-letter amino acid

VVYPWTQ

Peptide length

Peptide mass

Experimental mass	Theoretical mass
N.D	892.03 Da ^c

Net charge

0.00 ^c

Isoelectric point (pI)

5.92 ^c

IC₅₀

N.D

pIC₅₀

N.D

GRAVY

0.0571^c

Hydrophilic residue ratio

57.14%^c

Peptide calculator

Peptide source & Food-borne protein(s) search

Classification	Animal
Organism/Source	Bovine
Precursor protein	Hemoglobin β-chain
Residue position	f(32-38)
Precursor protein(s) search	Source.1: DFBPPR16819 ---- Animal proteins ---- Hemoglobin subunit beta Source.2: DFBPPR18509 ---- Animal proteins ---- Hemoglobin fetal subunit beta Source.3: DFBPPR8940 ---- Animal proteins ---- Hemoglobin subunit beta Source.4: DFBPPR9275 ---- Animal proteins ---- Hemoglobin subunit epsilon Source.5: DFBPPR9704 ---- Animal proteins ---- Hemoglobin subunit theta Source.6: DFBPPR12445 ---- Animal proteins ---- Hemoglobin subunit beta-1/2 Source.7: DFBPPR12812 ---- Animal proteins ---- Hemoglobin subunit gamma Source.8: DFBPPR12916 ---- Animal proteins ---- Hemoglobin subunit epsilon Source.9: DFBPPR13247 ---- Animal proteins ---- Hemoglobin subunit beta Source.10: DFBPPR13439 ---- Animal proteins ---- Hemoglobin subunit beta-A Source.11: DFBPPR13453 ---- Animal proteins ---- Hemoglobin subunit beta-C Source.12: DFBPPR13465 ---- Animal proteins ---- Hemoglobin fetal subunit beta Source.13: DFBPPR13474 ---- Animal proteins ---- Hemoglobin subunit epsilon-1 Source.14: DFBPPR13618 ---- Animal proteins ---- Hemoglobin subunit beta Source.15: DFBPPR13695 ---- Animal proteins ---- Hemoglobin subunit beta-C Source.16: DFBPPR13859 ---- Animal proteins ---- Hemoglobin fetal subunit beta
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

VV-hemorphin-5 have opioid activity to some degree. Although in comparison with other hemorphins, VV-hemorphin-5 has a higher IC₅₀ value, it did not indicate that it has a lower physiological function. It's a (μ > δ)-receptor^[1].

Table 1 Opioid activity of hemorphins
Hemorphins	Structure	IC₅₀ (μM)	References
Hemorphin-4	YPWT	45.2	[2]
Hemorphin-5	YPWTQ	46.3	[2]
Hemorphin-6	YPWTQR	4.3	[3]
Hemorphin-7	YPWTQRF	2.9	[4]
Hemorphin-8	YPWTQRFF	4.6	[4]
VV-hemorphin-5	VVYPWTQ	78.2	－
LVV-hemorphin-5	LVVYPWTQ	80.5	－
LVV-hemorphin-6	LVVYPWTQR	90.0	[3]
VV-hemorphin-7	VVYPWTQRF	34.3	[5]
LVV-hemorphin-7	LVVYPWTQRF	29.1	[5]
Normorphin	－	0.1	[5]

Values indicate concentration (μM) causing 50% inhibition (IC₅₀)of electrically induced contraction of the guinea-pig ileum myenteric plexus/longitudinal muscle preparation (GPI).

Specific target protein(s)

Specific Target Protein(s):
Mu-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])(C(C)C)C(=O)N[C@@]([H])(C(C)C)C(=O)N[C@@]([H])(Cc1ccc(O)cc1)C(=O)N1[C@@]([H])(CCC1)C(=O)N[C@@]([H])(CC(=CN2)C1=C2C=CC=C1)C(=O)N[C@@]([H])([C@]([H])(O)C)C(=O)N[C@@]([H])(CCC(=O)N)C(=O)O

Preparation method

Mode of preparation	Enzymatic hydrolysis
Enzyme(s)/starter culture	Hydrolysis with pepsin.

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]	DFBPACEI1118, DFBPACEI2151
[D2]	DFBPDPIV0224
[D3]	DFBPMUFU0221

BIOPEP-UWM

[D4]

2571, 9277, 9635

APD

[D5]

BioPepDB

[D6]

MBPDB

[D7]

Reference(s)

Primary literature	Zhao Q, Piot JM. Investigation of inhibition angiotensin-converting enzyme (ACE) activity and opioid activity of two hemorphins, LVV-hemorphin-5 and VV-hemorphin-5, isolated from a defined peptic hydrolysate of bovine hemoglobin. Neuropeptides. 1997 Apr;31(2):147-53. PMID: 9179868 DOI: 10.1016/s0143-4179(97)90084-6
Other literature(s)	[1] Teschemacher H. Opioid receptor ligands derived from food proteins.[J]. Current Pharmaceutical Design, 2003, 9(16):1331-1344. [2] Brantl V, Gramsch C, Lottspeich F, Henschen A,Jaeger K H, Herz A. Novel opioid peptides derived from mitochondrial cytochrome b: cytochrophins. Eur J Pharmacol 1985; 111 : 293. [3] Glamsta E L, Marklund, A, Hellman U, Wernstedt C, Terenius L, Nyberg F. Isolation and characterization of a hemoglobin- derived opioid peptide from the human pituitary gland. Regul Pept 1991; 34: 169-179. [4] Zhao Q Y, Plot J M, Sannier F, Guillochon D. Peptic hemoglobin hydrolysis in an ultrafiltration reactor at pilot plant scale generates opioid peptides. Ann NY Acad Sci 1995; 750: 452-459. [5] Piot J M, Zhao Q Y, Guillochon D, Thomas D. Isolationand characterization of two opioid peptides from a bovine hemoglobin peptic hydrolysate. Biochem Biophys Res Commun 1992; 189: 101-110. [6] Nyberg F, Sanderson K, Glämsta E L. The hemorphins: a new class of opioid peptides derived from the blood protein hemoglobin.[J]. Peptide Science, 1997, 43(2):147-156.
PubDate	1997