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2-[2-({1-[1-(2-amino-5-carbamimidamidopentanoyl)pyrrolidine-2-carbonyl]pyrrolidin-2-yl}formamido)acetamido]-3-phenylpropanoic acid
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ChemBase ID:
103766
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Molecular Formular:
C27H40N8O6
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Molecular Mass:
572.6565
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Monoisotopic Mass:
572.30708104
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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
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Cite this record
CBID:103766 http://www.chembase.cn/molecule-103766.html
NAMES AND DATABASE IDS
NAMES AND DATABASE IDS
Names Database IDs
IUPAC name
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2-[2-({1-[1-(2-amino-5-carbamimidamidopentanoyl)pyrrolidine-2-carbonyl]pyrrolidin-2-yl}formamido)acetamido]-3-phenylpropanoic acid
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IUPAC Traditional name
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2-[2-({1-[1-(2-amino-5-carbamimidamidopentanoyl)pyrrolidine-2-carbonyl]pyrrolidin-2-yl}formamido)acetamido]-3-phenylpropanoic acid
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Synonyms
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Bradykinin Fragment 1-5
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Arg-Pro-Pro-Gly-Phe
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BRADYKININ, Fragment 1-5
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CAS Number
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MDL Number
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PubChem SID
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PubChem CID
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DATA SOURCES
DATA SOURCES
All Sources Commercial Sources Non-commercial Sources
CALCULATED PROPERTIES
CALCULATED PROPERTIES
JChem
Acid pKa
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3.3206964
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H Acceptors
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10
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H Donor
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7
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LogD (pH = 5.5)
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-5.8470497
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LogD (pH = 7.4)
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-4.165865
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Log P
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-3.654658
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Molar Refractivity
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158.616 cm3
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Polarizability
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57.549 Å3
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Polar Surface Area
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224.04 Å2
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Rotatable Bonds
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13
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Lipinski's Rule of Five
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false
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DETAILS
DETAILS
Sigma Aldrich
Sigma Aldrich -
B1401
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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. |
PATENTS
PATENTS
PubChem Patent
Google Patent