BIOPEP-UWM: Report

ID 380
Name Bitter peptide
sequence
FFVAPFPEVFGK
Function:
Bitter peptide identified in tryptic hydrolysate of casein. Showed the bitterness in 0.1% water solution. The bitterness of FFVAPFPEVFGK was identical as in 0.1% phenylalanine water solution.
 
Number of residues
12
Activity code
bi
Activity :
bitter
Chemical mass 1384.6148 Monoisotopic mass 1383.7204
EC50 :
0.00 µM


Bibliographic data:
Authors
Matoba T., Hata T.
Title
Relationship between bitterness of peptides and their chemical structures. Agric Biol. Chem. 36, 1423 – 1431, 1972.
Year Source
1972 Journal


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


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

InChI=1S/C72H97N13O15/c1-43(2)60(83-65(92)54(40-48-26-14-8-15-27-48)79-62(89)50(74)38-46-22-10-6-11-23-46)68(95)76-45(5)70(97)84-36-20-31-56(84)67(94)81-55(41-49-28-16-9-17-29-49)71(98)85-37-21-32-57(85)66(93)78-51(33-34-59(87)88)64(91)82-61(44(3)4)69(96)80-53(39-47-24-12-7-13-25-47)63(90)75-42-58(86)77-52(72(99)100)30-18-19-35-73/h6-17,22-29,43-45,50-57,60-61H,18-21,30-42,73-74H2,1-5H3,(H,75,90)(H,76,95)(H,77,86)(H,78,93)(H,79,89)(H,80,96)(H,81,94)(H,82,91)(H,83,92)(H,87,88)(H,99,100)/t45-,50-,51-,52-,53-,54-,55-,56-,57-,60-,61-/m0/s1

InChIKey: ILZZTQYNTRWQSJ-QUXGTSCRSA-N


Other references concerning bitterness:

Matoba T., Nagayashi C., Hayashi R., Hata T., 1969, Bitter peptides in tryptic hydrolysate of casein. Agric. Biol. Chem., 33, 1662-1663

Lemieux L., Simard R. E., 1992, 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


Inhibitor of Angiotensin-Converting Enzyme (ACE) (EC 3.4.15.1) (MEROPS ID: M02-001) according to the AHTPDB database; the BIOPEP-UWM database of bioactive peptides (ID 7800); the DFBP database; the PepBank database
Anticancer peptide according to the BIOPEP-UWM database of bioactive peptides (ID 8311); the DFBP database

Predicted antithrombotic peptide according to the BIOPEP-UWM Virtual database (ID 209); the DFBP database


Database reference:
AHTPDB: ID 1347, 1656, 3669, 3748, 4272, 5052, 5534, 5550, 5557, 5834, 5846, 6704

BIOPEP-UWM database of bioactive peptides: ID 7800; 8311

BIOPEP-UWM Virtual database: ID 209

ChemSpider: ID 17295906

DFBP: ID DFBPANHY0180; DFBPANHY0888; DFBPACEI0331; DFBPANCA0110; DFBPMUFU0097

EROP-Moscow: ID E01836

FeptideDB: ID 7800; 8311

PepBank: Peptide FFVAPFPEVFGK

PubChem: CID 16139402

SATPdb ID: satpdb23541