Ras inhibitory peptide
Basic information
- CAS
159088-48-9- Standard SMILES
CC(C)[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)C(C)C- InChIKey
KDEHBKGSNFLJSF-QMAXXTOWSA-N- Molecular formula
- C53H91N19O11
- Average molar mass
- 1,170.4 g/mol
- Monoisotopic mass
- 1,169.7145448
Names & identifiers
- Preferred name
- Ras inhibitory peptide
- IUPAC
- (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-1-[(2S)-2-[[(2S)-1-[(2S)-1-[(2S)-1-[(2S)-2-amino-3-methylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid
- English name
- RAS INHIBITORY PEPTIDE
- Molecular formula
- C53H91N19O11
- Molecular weight
- 1170.41
Names & synonyms
Ras inhibitory peptide159088-48-91azeH-VPPPVPPRRR-OHorb1692898CHEMBL2372045DTXSID00332156Sos SH3 domain inhibitor inhibitorHY-P2157C53H91N19O11MFCD00237248AKOS040755814
Show more names
VPPPVPPRRR-NH2Sos SH3 domain inhibitorVAL-PRO-PRO-PRO-VAL-PRO-PRO-ARG-ARG-ARGHSOS (1149-1158) N10 SH3 BINDING DOMAINL-Arginine, L-valyl-L-prolyl-L-prolyl-L-prolyl-L-valyl-L-prolyl-L-prolyl-L-arginyl-L-arginyl-
FR108435DB-230602CS-0109286T37422H-Val-Pro-Pro-Pro-Val-Pro-Pro-Arg-Arg-Arg-OHL-valyl-l-prolyl-l-prolyl-l-prolyl-l-valyl-l-prolyl-l-prolyl-l-arginyl-l-arginyl-l-arginine(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-1-[(2S)-2-[[(2S)-1-[(2S)-1-[(2S)-1-[(2S)-2-amino-3-methyl-butanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]-3-methyl-butanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]-5-guanidino-pentanoyl]amino]-5-guanidino-pentanoyl]amino]-5-guanidino-pentanoic acidL-Valyl-L-prolyl-L-prolyl-L-prolyl-L-valyl-L-prolyl-L-prolyl-N~5~-(diaminomethylidene)-L-ornithyl-N~5~-(diaminomethylidene)-L-ornithyl-N~5~-(diaminomethylidene)-L-ornithine
Properties
Computed structural properties
- XLogP
- -5.4
- Topological polar surface area
- 474 Ų
- Hydrogen bond donors
- 12
- Hydrogen bond acceptors
- 15
- Rotatable bonds
- 28
- Heavy atoms
- 83
- Formal charge
- 0
- Complexity
- 2,430
Physicochemical properties
- Density
- 1.52 · 1.52±0.1 g/cm3(Predicted)
- storage temp.
- 20 °C · −20°C
- solubility
- 30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: Miscible; PBS (pH 7.2): 10 mg/ml
- form
- A crystalline solid
- pka
- 3.31 · 3.31±0.10(Predicted)
- Sequence
- Val-Pro-Pro-Pro-Val-Pro-Pro-Arg-Arg-Arg
- WGK Germany
- 3 · 3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
Chemistry & industry
Applications
DescriptionSon of sevenless homolog 1 (Sos1) is a guanine nucleotide exchange factor (GEF) that directs the exchange of Ras-GDP to Ras-GTP by binding to SH3 domains of the growth factor receptor-bound protein 2 (Grb2), leading to the activation of ERK. Ras inhibitory peptide is a synthetic peptide that contains the sequence PVPPR, which corresponds to a region within human Sos1 that interacts with an SH3 domain of Grb2. It specifically blocks the interaction of the GEF with Grb2, preventing an interaction that is essential for Ras activation by receptor tyrosine kinases, including epidermal growth factor receptor.
UsesRas Inhibitory Peptide (VPPPVPPRRR) is a Ras inhibitor with antitumor activity[1].
Related reactions
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Compound notes
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