Record tools

Copy identifiers or export this single peptide record for a local research note.

PEPDIA-INT-001004

Gold

Cyclo(Trp-Leu), Diketopiperazine (WL)

Quality

Source DBs

Activities

Source refs

Literature

Patents

Integrated record

Sequence and molecular profile

Indexed sequence2 aa

1WL

Length

Molecular weight

317.39 Da

Formula

C17H23N3O3

Structure type

Linear

Synthesis

Non-ribosomal

Chirality

Family

Gene

Residue composition

Physicochemical profile

Hydrophobic2

Membrane affinity proxy

Polar0

Solubility proxy

Charged0

Net charge proxy +0

Aromatic1

Binding interaction proxy

Versioned scientific descriptors

Physicochemical properties and standard representations

calculated sequence and structure

Reported properties

Legacy compatibility fields are materialized from the versioned PepDiana computed release; no separate source-reported property is available.

Computed properties

physchem-20260620

Molecular weight

317.3828 Da

Molecular formula

C17H23N3O3

Theoretical pI

5.525

Net charge at pH 7

-0.2399

GRAVY

1.45

Instability index

66.7

Aromaticity

0.5

Topological polar surface area

108.21 Å²

cLogP

1.6532

Hydrogen-bond donors

Hydrogen-bond acceptors

Rotatable bonds

Method: PepDiana sequence/structure descriptor pipeline

Tool: Biopython+RDKit · Biopython 1.85; RDKit 2024.09.6

Calculated: 2026-06-20T11:01:38.358971+00:00

Assumptions: ph=7; termini=free N-terminus and free C-terminus for simple linear peptides; stereochemistry=standard L-amino acids; smiles_length_limit=200

Sequence representations

representations-20260620 · RDKit 2024.09.6

ProForma 2.0

validated simple linear

HELM 2.0

validated simple linear

PEPTIDE1{W.L}$$$$V2.0

Canonical SMILES

validated

CC(C)CC(NC(=O)C(N)Cc1c[nH]c2ccccc12)C(=O)O

Isomeric SMILES

validated

CC(C)C[C@H](NC(=O)[C@@H](N)Cc1c[nH]c2ccccc12)C(=O)O

Follow-up research

External analysis tools

Run BLASTPSearch similar protein or peptide sequences at NCBI.Search UniProtLook for related UniProtKB entries using the sequence.Search PubMedFind literature context for this peptide record.Search PubChemOpen chemistry search with the canonical SMILES string.

Links open third-party resources with the current PepDiana sequence, record name, or chemistry notation as the initial query.

Research workflow

Citation and local history

BibTeX

@misc{PEPDIA-INT-001004,
  title = {Cyclo(Trp-Leu), Diketopiperazine (WL)},
  author = {{PepDiana Consortium}},
  year = {2026},
  howpublished = {PepDiana Multifunctional Peptide Database},
  url = {http://127.0.0.1:3004/peptides/PEPDIA-INT-001004},
  note = {Accessed from local PepDiana development build}
}

APA-style note

Cyclo(Trp-Leu), Diketopiperazine (WL). (2026). PepDiana record PEPDIA-INT-001004. PepDiana Multifunctional Peptide Database. http://127.0.0.1:3004/peptides/PEPDIA-INT-001004

This record is saved to local recent-view history so it can reappear on the peptide browser page.

Integrated source-database annotations

Biological activity (66 records)

Stable record	Activity	Subtype	Value	Target	Assay method	Source
CTPDB_P001004_ACT_ahtpdb_0001	Metabolic/Cardiovascular	ACE Inhibitor	20.0 mM	Unknown	Not reported by source	1463ahtpdb / linked
CTPDB_P001004_ACT_ahtpdb_0002	Metabolic/Cardiovascular	ACE Inhibitor	29.9 µM	Unknown	Cushman and Cheung (1971)	1900ahtpdb / linked
CTPDB_P001004_ACT_ahtpdb_0003	Metabolic/Cardiovascular	ACE Inhibitor	Not available for this observation	Unknown	Not reported by source	2968ahtpdb / linked
CTPDB_P001004_ACT_ahtpdb_0000	Metabolic/Cardiovascular	ACE Inhibitor	Not available for this observation	Unknown	Not reported by source	4724ahtpdb / linked
CTPDB_P001004_ACT_ahtpdb_0004	Metabolic/Cardiovascular	ACE Inhibitor	65.0 µM	Unknown	Not reported by source	5181ahtpdb / linked
CTPDB_P001004_ACT_ahtpdb_0005	Metabolic/Cardiovascular	ACE Inhibitor	29.9 µM	Unknown	Cushman and Cheung (1971)	6216ahtpdb / linked
CTPDB_P001004_ACT_ahtpdb_0006	Metabolic/Cardiovascular	ACE Inhibitor	65.0 µM	Unknown	Cushman and Cheung (1971)	6220ahtpdb / linked
CTPDB_P001004_ACT_ahtpdb_0007	Metabolic/Cardiovascular	ACE Inhibitor	29.9 µM	Unknown	Lieberman's method	6862ahtpdb / linked
CTPDB_P001004_ACT_camp_0008	Antimicrobial	Antibacterial	Not available in the current structured import	Unknown	Not reported by source	CAMPSQ22016camp / linked
CTPDB_P001004_ACT_camp_0009	Antimicrobial	Anti-Gram+	Not available in the current structured import	Unknown	Not reported by source	CAMPSQ22016camp / linked
CTPDB_P001004_ACT_camp_0010	Antimicrobial	Anti-Gram-	Not available in the current structured import	Unknown	Not reported by source	CAMPSQ22016camp / linked
CTPDB_P001004_ACT_dbaasp_0011	Antimicrobial	-	250 µg/ml	Bacillus subtilis MTCC 2756	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0012	Antimicrobial	-	500 µg/ml	Bacillus subtilis MTCC 2756	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0013	Antimicrobial	-	125 µg/ml	Staphylococcus aureus MTCC 902	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0014	Antimicrobial	-	250 µg/ml	Staphylococcus aureus MTCC 902	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0015	Antimicrobial	-	500 µg/ml	Escherichia coli MTCC 2622	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0016	Antimicrobial	-	1000 µg/ml	Escherichia coli MTCC 2622	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0017	Antimicrobial	-	NA	Pseudomonas aeruginosa MTCC 2642	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0018	Antimicrobial	-	NA	Staphylococcus epidermidis MTCC 435	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0019	Antimicrobial	-	NA	Proteus mirabilis MTCC 425	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0020	Antimicrobial	-	NA	Vibrio cholerae MTCC 3905	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0021	Antimicrobial	-	NA	Klebsiella pneumoniae MTCC 109	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0022	Antimicrobial	-	125 µg/ml	Staphylococcus simulans MTCC 3610	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0023	Antimicrobial	-	125 µg/ml	Staphylococcus simulans MTCC 3610	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0024	Antimicrobial	-	NA	Salmonella enterica subsp. enterica serovar Typhi MTCC 3216	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0025	Antimicrobial	-	16 µg/ml	Aspergillus flavus MTCC 183	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0026	Antimicrobial	-	16 µg/ml	Candida albicans MTCC 277	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0027	Antimicrobial	-	8 µg/ml	Fusarium oxysporum MTCC 284	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0028	Antimicrobial	-	32 µg/ml	Rhizoctonia solani MTCC 4634	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0029	Antimicrobial	-	32 µg/ml	Penicillium expansum MTCC 2006	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0030	Antimicrobial	-	64 µg/ml	Goffeauzyma gastrica MTCC 1715	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0031	Antimicrobial	-	64 µg/ml	Candida tropicalis MTCC 184	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0032	Antimicrobial	-	NA	Human colon adenocarcinoma HCT 116	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0033	Antimicrobial	-	>100 µM	Human myelogenous leukemia K562	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0034	Antimicrobial	-	>100 µM	Human ovarian adenocarcinoma A2780	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0035	Antimicrobial	-	>100 µM	Human ovarian adenocarcinoma A2780CisR	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0036	Antimicrobial	-	>200 µM	Human cervical carcinoma HeLa	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0037	Antimicrobial	-	>200 µM	Human hepatocellular carcinoma HepG2	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0038	Antimicrobial	-	>200 µM	Human lung carcinoma A549	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0039	Antimicrobial	-	>200 µM	Human breast adenocarcinoma MCF-7	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0040	Antimicrobial	-	256 µg/ml	Bacillus subtilis ATCC 23857	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0041	Antimicrobial	-	128 µg/ml	Staphylococcus aureus ATCC 12600	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0042	Antimicrobial	-	NA	Staphylococcus epidermidis ATCC 51625	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0043	Antimicrobial	-	128 µg/ml	Staphylococcus simulans ATCC 27848	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0044	Antimicrobial	-	512 µg/ml	Escherichia coli ATCC 35218	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0045	Antimicrobial	-	NA	Klebsiella pneumoniae ATCC 43816	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0046	Antimicrobial	-	NA	Proteus mirabilis ATCC 21100	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0047	Antimicrobial	-	NA	Pseudomonas aeruginosa ATCC 10145	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0048	Antimicrobial	-	16 µg/ml	Aspergillus flavus ATCC 204304	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0049	Antimicrobial	-	16 µg/ml	Candida albicans ATCC 10231	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0050	Antimicrobial	-	64 µg/ml	Goffeauzyma gastrica ATCC 32042	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0051	Antimicrobial	-	NA	Trichophyton rubrum ATCC 28191	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0052	Antimicrobial	-	8 µg/ml	Fusarium oxysporum ATCC 14838	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0053	Antimicrobial	-	32 µg/ml	Rhizoctonia solani ATCC 10182	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0054	Antimicrobial	-	32 µg/ml	Penicillium expansum ATCC 16104	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dbaasp_0055	Antimicrobial	-	64 µg/ml	Alternaria brassicae ATCC 66981	Not reported by source	DBAASPS_7134_chain0dbaasp / linked
CTPDB_P001004_ACT_dramp_0056	Antimicrobial	-	Not available in the current structured import	Unknown	Not reported by source	DRAMP34357dramp / linked
CTPDB_P001004_ACT_dramp_0057	Anticancer	-	Not available in the current structured import	Unknown	Not reported by source	DRAMP34357dramp / linked
CTPDB_P001004_ACT_fermfoodb_0058	Metabolic/Cardiovascular	ACE Inhibitor	65.0 µM	Unknown	RPHLC and automated Edman degradation with a gas/liquid-phase protein sequencer	FermFooDB_Soyabean_FMDB861fermfoodb / linked
CTPDB_P001004_ACT_fermfoodb_0059	Metabolic/Cardiovascular	ACE Inhibitor	29.9 µM	Unknown	RPHPLC and automated degardation using gas/liquid phase protein sequencer	FermFooDB_Soyabean_FMDB994fermfoodb / linked
CTPDB_P001004_ACT_fermfoodb_0061	Metabolic/Cardiovascular	ACE Inhibitor	29.9 µM	Unknown	automated Edman degardation with a gas/liquid phase protein sequencer	FermFooDB_Tofuyu_FMDB1977fermfoodb / linked
CTPDB_P001004_ACT_fermfoodb_0060	Metabolic/Cardiovascular	ACE Inhibitor	29.9 µM	Unknown	RPHPLC and automated degardation using gas/liquid phase protein sequencer	FermFooDB_Tofuyu_FMDB994fermfoodb / linked
CTPDB_P001004_ACT_plantpepdb_0062	Metabolic/Cardiovascular	Antihypertensive	Not available for this observation	Unknown	Not reported by source	PPepDB_3839plantpepdb / linked
CTPDB_P001004_ACT_plantpepdb_0063	Metabolic/Cardiovascular	ACE Inhibitor	Not available for this observation	Unknown	Not reported by source	PPepDB_3839plantpepdb / linked
CTPDB_P001004_ACT_plantpepdb_0064	Unknown	Anxiolytic-like-activity	Not available in the current structured import	Unknown	Not reported by source	PPepDB_3839plantpepdb / linked
CTPDB_P001004_ACT_satpdb_0065	Metabolic/Cardiovascular	Antihypertensive	Not available for this observation	Unknown	Not reported by source	satpdb20928satpdb / linked

Sequence-linked cross-layer evidence

Linked primary-literature evidence

Records

Papers

Positive

Negative

Primary identities

These observations were collected directly from primary literature and linked by identical normalized sequence. They remain a separate evidence layer and do not overwrite Integrated source-database annotations.

View PEPDIA-PLP-004157 View all experimental records

Provenance

Source database records (17)

ahtpdb

4724

Raw sequence

ahtpdb

2968

Raw sequence

ahtpdb

1463

Raw sequence

ahtpdb

1900

Raw sequence

ahtpdb

6216

Raw sequence

ahtpdb

6220

Raw sequence

ahtpdb

6862

Raw sequence

ahtpdb

5181

Raw sequence

camp

CAMPSQ22016

Raw sequence

dbaasp

DBAASPS_7134_chain0

Raw sequence

dramp

DRAMP34357

Raw sequence

fermfoodb

FermFooDB_Soyabean_FMDB861

Raw sequence

fermfoodb

FermFooDB_Soyabean_FMDB994

Raw sequence

fermfoodb

FermFooDB_Tofuyu_FMDB994

Raw sequence

fermfoodb

FermFooDB_Tofuyu_FMDB1977

Raw sequence

plantpepdb

PPepDB_3839

Raw sequence

satpdb

satpdb20928

Raw sequence

Citation trail

Literature (11 records)

What are the ideal properties for functional food peptides with antihypertensive effect? A computational peptidology approach.

Zhou P et al.

Food Chem. 2013 Dec 1;141(3):2967-73.2013PMID 23871047

Glycinyl-Histidinyl-Serine (GHS), a Novel Rapeseed Protein-Derived Peptide Has Blood Pressure-Lowering Effect in Spontaneously Hypertensive Rats

Rong He; Sunday A. Malomo; Abraham T. Girgih; Xingrong Ju; Rotimi E. Aluko

Journal of agricultural and food chemistry. 61(35): 8396-4022013PMID 23919612

Structural requirements of Angiotensin I-converting enzyme inhibitory peptides: quantitative structure-activity relationship study of di- and tripeptides.

Wu J1, Aluko RE, Nakai S.

J Agric Food Chem. 2006 Feb 8;54(3):732-8.2006PMID 16448176

Vegetable foods: A cheap source of proteins and peptides with antihypertensive, antioxidant, and other less occurrence bioactivities.

M C García, P Puchalska, C Esteve, M L Marina

Talanta 03/2013; 106C:328-349.2013PMID 23598136

Angiotensin I-converting enzyme inhibitory peptides isolated from tofuyo fermented soybean food

Kuba, M et al.

Biosci Biotechnol Biochem 67 p.1278-832003PMID 12843654

Production of angiotensin I-converting enzyme inhibitory peptides from soybean protein with Monascus purpureus acid proteinase

Kuba, M et al.

Process Biochem 40 p.2191-21962005

Integration of QSAR modelling and QM/MM analysis to investigate functional food peptides with antihypertensive activity

Jin Tan et al.

Molecular Simulation Volume 39, Issue 12, 20132013

-

--PMID 24120705

Purification, structural elucidation and bioactivity of tryptophan containing diketopiperazines, from Comamonas testosteroni associated with a rhabditid entomopathogenic nematode against major human-pathogenic bacteria.

Kumar SN, Mohandas C, Nambisan B

Peptides2014PMID 22617493

Purification, structural elucidation and bioactivity of tryptophan containing diketopiperazines, from Comamonas testosteroni associated with a rhabditid entomopathogenic nematode against major human-pathogenic bacteria.

Kumar SN, Mohandas C, Nambisan B

Peptides2014PMID 32806659

-

--PMID 23871011

Audit surface

Raw annotations and release metadata

Integrated record last updated: 2026-04-15T00:59:10.991164+00:00

Modification summary

No structured modification annotations are available for this record.

ADMET

{
  "toxicity": [
    {
      "unit": "µM",
      "value": ">100",
      "source_db": "dbaasp",
      "assay_method": "50% Cell death",
      "toxicity_type": "Cytotoxic",
      "target_cellline": "Vero cells"
    },
    {
      "unit": "µM",
      "value": "100",
      "source_db": "dbaasp",
      "assay_method": "50% Cell death",
      "toxicity_type": "Cytotoxic",
      "target_cellline": "Human fibroblasts"
    }
  ]
}

Source metadata

[
  {
    "source_db": "ahtpdb",
    "organism_name": "Unknown"
  },
  {
    "source_db": "camp",
    "organism_name": "Unknown"
  },
  {
    "source_db": "dbaasp",
    "organism_name": "Unknown"
  },
  {
    "source_db": "dramp",
    "organism_name": "Unknown"
  },
  {
    "source_db": "fermfoodb",
    "organism_name": "Unknown"
  },
  {
    "source_db": "plantpepdb",
    "organism_name": "Unknown"
  },
  {
    "source_db": "satpdb",
    "organism_name": "Unknown"
  }
]

Structure metadata

{
  "source_db": "satpdb",
  "dssp_states": "CC"
}