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Glutamyl-histidyl-isoleucyl-prolyl-alanine

HCID 5487438
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Basic information

CAS
137235-80-4
Standard SMILES
CC[C@H](C)[C@H](NC(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@@H](N)CCC(=O)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C)C(=O)O
InChIKey
VWJLJHZPMZGDDV-HOCDWTQPSA-N
Molecular formula
C25H39N7O8
Average molar mass
565.6 g/mol
Monoisotopic mass
565.28601121

Overview

binds fibrinogen & inhbits platelet aggregation & adhesion to fibrinogen & vitronectin

Names & identifiers

Preferred name
Glutamyl-histidyl-isoleucyl-prolyl-alanine
IUPAC
(4S)-4-amino-5-[[(2S)-1-[[(2S,3S)-1-[(2S)-2-[[(1S)-1-carboxyethyl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
English name
FIBRINOGEN-BINDING PEPTIDE
Molecular formula
C25H39N7O8
Molecular weight
565.62

Names & synonyms

137235-80-4Glu-his-ile-pro-alaGlutamyl-histidyl-isoleucyl-prolyl-alanineDTXSID80160116RefChem:143686DTXCID5082607Fibrinogen-Binding Peptide(4S)-4-amino-5-[[(2S)-1-[[(2S,3S)-1-[(2S)-2-[[(1S)-1-carboxyethyl]carbamoyl]pyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-5-oxopentanoic acidorb321061orb1983830CHEMBL1409520SCHEMBL29613679
Show more names
EHIPAH-GLU-HIS-ILE-PRO-ALA-OHFibrinogen-Binding Peptide (3)Fibrinogen-Binding Peptide butylL-α-Glutamyl-L-histidyl-L-isoleucyl-L-prolyl-L-alanineL-Alanine, L-α-glutamyl-L-histidyl-L-isoleucyl-L-prolyl-
SCHEMBL29973360HY-P1741TP1736NCGC00167251-01DA-63437MS-30246CS-0095106F3204

Properties

Computed structural propertiesFilling in

XLogP
-3.1
Topological polar surface area
237 Ų
Hydrogen bond donors
7
Hydrogen bond acceptors
10
Rotatable bonds
15
Heavy atoms
40
Formal charge
0
Complexity
948

Physicochemical properties

Boiling point
1067.8 · 1067.8±65.0 °C(Predicted)
Density
1.343 · 1.343±0.06 g/cm3(Predicted)
storage temp.
-15 °C · -15°C
pka
3.7 · 3.70±0.10(Predicted)
form
Solid
color
White to off-white
Sequence
Glu-His-Ile-Pro-Ala

Chemistry & industry

Applications · 1 item

UsesFibrinogen-Binding Peptide (designed by anticomplementarity hypothesis) is a presumptive peptide mimic of the vitronectin binding site on the fibrinogen receptor. Fibrinogen-Binding Peptide binds fibrinogen and inhibits both the adhesion of platelets to fibrinogen and platelet aggregation, and also inhibits the adhesion of platelets to vitronectin[1].

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Database identifiers

CAS
137235-80-4
PubChem CID
5487438
DTXSID
DTXSID80160116
ChEMBL
CHEMBL1409520
Nikkaji
J402.026J