BIOPEP-UWM: Report

ID 460
Name Bitter peptide
sequence
GPFPIIV
Function:
Bitter peptide. Q value (i. e. average amount of free energy needed to transfer amino acid chains from ethanol to water) = 9279.7 J / (Mol x res). Rcaf = 2.9-5.9
 
Number of residues
7
Activity code
bi
Activity :
bitter
Chemical mass 741.9148 Monoisotopic mass 741.4411
EC50 :
0.00 µM


Bibliographic data:
Authors
Lemieux L., Simard R. E.
Title
Bitter flavour in dairy products. II. A review of bitter peptides from caseins: their formation, isolation and identification, structure masking and inhibition. Lait, 72, 335-382, 1992
Year Source
1992 Journal


Additional information:
BIOPEP-UWM database of sensory peptides and amino acids


SMILES: NCC(=O)N1[C@@]([H])(CCC1)C(=O)N[C@@H](CC1=CC=C(C=C1))C(=O)N1[C@@]([H])(CCC1)C(=O)N[C@@]([H])([C@]([H])(CC)C)C(=O)N[C@@]([H])([C@]([H])(CC)C)C(=O)N[C@@]([H])(C(C)C)C(=O)O

InChI=1S/C38H59N7O8/c1-7-23(5)31(36(50)43-32(24(6)8-2)35(49)41-30(22(3)4)38(52)53)42-34(48)28-17-13-19-45(28)37(51)26(20-25-14-10-9-11-15-25)40-33(47)27-16-12-18-44(27)29(46)21-39/h9-11,14-15,22-24,26-28,30-32H,7-8,12-13,16-21,39H2,1-6H3,(H,40,47)(H,41,49)(H,42,48)(H,43,50)(H,52,53)/t23-,24-,26-,27-,28-,30-,31-,32-/m0/s1

InChIKey: VBXAFDSUVWHGGB-LWAQOXNASA-N


Previous references concerning peptide:

MatobaT., Hayashi R., Hata T., 1970, Isolation of bitter peptides from tryptic hydrolysate of casein and their chemical structure. Agric. Biol. Chem., 34, 1235-1243

Pelissier J. P., Mercier J. C., Ribadeau-Dumas B., 1974, Etude de la proteolyses des caseines alpha s1 et beta bovines par la presure. Ann. Biol. Anim. Biochim. Biophys., 14, 343-362

Hashimoto H., Aoyagi H., Izumiya N., 1980, Synthetic identification of bitter heptapeptide in tryptic hydrolysate of casein. Bull. Chem. Soc. Jpn, 53, 2926-2928


Inhibitor of Angiotensin-converting enzyme (EC 3.4.15.1) (MEROPS ID: M02-001) according to the AHTPDB database, the BIOPEP database of bioactive peptides (ID 8159)

Predicted ligand of Thrombin (EC 3.4.21.5) (MEROPS ID: S01.217) (PDB code: 2BVR) according to the BIOPEP-UWM Virtual database (ID 220); the DFBP database


Database reference:

AHTPDB: ID 1806, 6754

BioPepDB: ID biopep00385

BIOPEP-UWM database of bioactive peptides: ID 8159

BIOPEP-UWM Virtual database: ID 220

ChemSpider: ID 9882264

DFBP: ID DFBPACEI0859; DFBPANTH0163; DFBPMUFU0184

EPA DSSTox: ID DTXCID60421717

EROP-Moscow: ID E14527

FeptideDB: ID 8159

J-GLOBAL: ID 200907034717127309

Nikkaji: ID J1.075.678B

PubChem: ID 11707541

SATPdb: ID satpdb12352