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23815-89-6 molecular structure
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2-[2-({1-[1-(2-amino-5-carbamimidamidopentanoyl)pyrrolidine-2-carbonyl]pyrrolidin-2-yl}formamido)acetamido]-3-phenylpropanoic acid

ChemBase ID: 103766
Molecular Formular: C27H40N8O6
Molecular Mass: 572.6565
Monoisotopic Mass: 572.30708104
SMILES and InChIs

SMILES:
NC(CCCNC(=N)N)C(=O)N1CCCC1C(=O)N1CCCC1C(=O)NCC(=O)NC(Cc1ccccc1)C(=O)O
Canonical SMILES:
O=C(NC(C(=O)O)Cc1ccccc1)CNC(=O)C1CCCN1C(=O)C1CCCN1C(=O)C(CCCNC(=N)N)N
InChI:
InChI=1S/C27H40N8O6/c28-18(9-4-12-31-27(29)30)24(38)35-14-6-11-21(35)25(39)34-13-5-10-20(34)23(37)32-16-22(36)33-19(26(40)41)15-17-7-2-1-3-8-17/h1-3,7-8,18-21H,4-6,9-16,28H2,(H,32,37)(H,33,36)(H,40,41)(H4,29,30,31)
InChIKey:
USSUMSBPLJWFSZ-UHFFFAOYSA-N

Cite this record

CBID:103766 http://www.chembase.cn/molecule-103766.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-[2-({1-[1-(2-amino-5-carbamimidamidopentanoyl)pyrrolidine-2-carbonyl]pyrrolidin-2-yl}formamido)acetamido]-3-phenylpropanoic acid
IUPAC Traditional name
2-[2-({1-[1-(2-amino-5-carbamimidamidopentanoyl)pyrrolidine-2-carbonyl]pyrrolidin-2-yl}formamido)acetamido]-3-phenylpropanoic acid
Synonyms
Bradykinin Fragment 1-5
Arg-Pro-Pro-Gly-Phe
BRADYKININ, Fragment 1-5
CAS Number
23815-89-6
MDL Number
MFCD00076260
PubChem SID
24891591
162102910
PubChem CID
4278577

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 4278577 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 3.3206964  H Acceptors 10 
H Donor LogD (pH = 5.5) -5.8470497 
LogD (pH = 7.4) -4.165865  Log P -3.654658 
Molar Refractivity 158.616 cm3 Polarizability 57.549 Å3
Polar Surface Area 224.04 Å2 Rotatable Bonds 13 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
MSDS Link
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
-20°C expand Show data source
Gene Information
human ... KNG1 (includes EG:3827)(3827) expand Show data source
Purity
≥97% (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - B1401 external link
Amino Acid Sequence
Arg-Pro-Pro-Gly-Phe
Biochem/physiol Actions
The bradykinin (BK) fragment (1-5) (RPPGF) is among the most stable of naturally occurring metabolites. It may be used as a marker for BK production in vivo. It is known that an intact Arg residue in the C-terminus is required for biological activities. BK 1-5 is the minimal peptide that inhibited α-thrombin-induced platelet aggregation and secretion and calcium mobilization. It also prevented α-thrombin from cleaving the thrombin receptor peptide, NATLDPRSFLLR, between arginine and serine. Such antithrombin activities of BK 1-5 may contribute to the cardioprotective nature of kinins.

REFERENCES

REFERENCES

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PATENTS

PATENTS

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INTERNET

INTERNET

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