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Norleual

Norleual is an angiotensin (Ang) IV analog, and acts as highly potent HGF/c-MET inhibitor (IC50 = 3 pM) that inhibits HGF-induced MDCK cell proliferation and invasion in vitro. It also is AT4 receptor antagonist, disrupts LTP stabilization. It shows antiangiogenic activity.

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Norleual(CAS 334994-34-2)

CAT No: R1054

CAS No: 334994-34-2

Synonyms/Alias: Norleual;334994-34-2;L-Phenylalanine,L-norleucyl-L-tyrosyl-L-leucyl-y(CH2-NH)-L-histidyl-L-prolyl-;(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-aminohexanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-methylpentyl]amino]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoic acid;AKOS025142100;DA-56260;PD080030;G91230;

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M.F/FormulaC41H58N8O7
M.W/Mr.774.9
SequenceXYLHPF(Modifications: X = Nle, Leu-3-His-4 peptide bond replaced with CH2NH)
InChIInChI=1S/C41H58N8O7/c1-4-5-12-32(42)37(51)47-33(20-28-14-16-31(50)17-15-28)38(52)46-30(19-26(2)3)24-44-34(22-29-23-43-25-45-29)40(54)49-18-9-13-36(49)39(53)48-35(41(55)56)21-27-10-7-6-8-11-27/h6-8,10-11,14-17,23,25-26,30,32-36,44,50H,4-5,9,12-13,18-22,24,42H2,1-3H3,(H,43,45)(H,46,52)(H,47,51)(H,48,53)(H,55,56)/t30-,32-,33?,34-,35-,36-/m0/s1
InChI KeyLOHDEFSMLITXTG-RZAPKHMUSA-N
Isomeric SMILESCCCC[C@@H](C(=O)NC(CC1=CC=C(C=C1)O)C(=O)N[C@@H](CC(C)C)CN[C@@H](CC2=CN=CN2)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC4=CC=CC=C4)C(=O)O)N
References

AngIV analogs such as norleual may also mimic the conformation of the hinge region of HGF. In norleual, the reduced peptide bond increases the rotatability around the 3-4-position, making the molecule more flexible. This may permit norleual to emulate hinge conformations in HGF that are normally induced by tertiary structure (kringles) to facilitate its interaction with the c-Met.

The Angiotensin IV Analog Nle-Tyr-Leu-ψ-(CH2-NH2)3-4-His-Pro-Phe (Norleual) Can Act as a Hepatocyte Growth Factor/c-Met Inhibitor

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