FTase inhibitor I
Basic information
- CAS
149759-96-6- Standard SMILES
CSCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC[C@@H](NC[C@@H](N)CS)C(C)C)C(=O)O- InChIKey
QISLMXIYRQCLIR-FUMNGEBKSA-N- Molecular formula
- C22H38N4O3S2
- Average molar mass
- 470.7 g/mol
- Monoisotopic mass
- 470.23853343
Overview
B 581 is a dipeptide obtained from the tetrapeptide Cys-Val-Phe-Met by reduction of the amide carbonyl groups of the Cys and Val residues. It has a role as a peptidomimetic and an EC 2.5.1.58 (protein farnesyltransferase) inhibitor.
Names & identifiers
- Preferred name
- FTase inhibitor I
- IUPAC
- (2S)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-amino-3-sulfanylpropyl]amino]-3-methylbutyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acid
- English name
- B581
- Molecular formula
- C22H38N4O3S2
- Molecular weight
- 470.69
Names & synonyms
FTase Inhibitor I149759-96-6B 581B581DTXSID30164381CHEBI:83620RefChem:921878DTXCID2086872CHEMBL91722(2S)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-amino-3-sulfanylpropyl]amino]-3-methylbutyl]amino]-3-phenylpropanoyl]amino]-4-methylsulfanylbutanoic acidL-Methionine, N-(N-(2-((2-amino-3-mercaptopropyl)amino)-3-methylbutyl)-L-phenylalanyl)-, (S-(R*,S*))-N-[(2S)-2-{[(2R)-2-amino-3-sulfanylpropyl]amino}-3-methylbutyl]-L-phenylalanyl-L-methionine
Show more names
B581 USP/EP/BPH-Cys-()-Val-()-Phe-Met-OHCYS-((R))-VAL-((R))-PHE-METH-CYS-(R)-VAL-(R)-PHE-MET-OHN-[(S)-2-((R)-2-Amino-3-mercapto-propylamino)-3-meN-[2(S)-[2(R)-AMINO-3-MERCAPTOPROPYLAMINO]-3-METHYL-BUTYL]-PHE-MET
L-Methionine, N-[(2S)-2-[[(2R)-2-amino-3-mercaptopropyl]amino]-3-methylbutyl]-L-phenylalanyl-B-581CBiol_001875H-Cys-psi(CH2NH)Val-psi(CH2NH)Phe-Met-OHBSPBio_001466KBioGR_000186KBioSS_000186H-Cys-psi(CH2NH)Val-psi(CH2NH)Phe-Met-OH trifluoroacetate salt
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 143 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 16
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 519
Physicochemical properties
- Boiling point
- 716.1 · 716.1±60.0 °C(Predicted)
- Density
- 1.161 · 1.161±0.06 g/cm3(Predicted)
- storage temp.
- 20 °C · −20°C
- solubility
- 2 O: · H2O: soluble
- form
- solid
- pka
- 3.04 · 3.04±0.10(Predicted)
- color
- white
- Water Solubility
- 1 mg/mLDMSO: · water: 1mg/mLDMSO: 5mg/mL
- UNSPSC Code
- 12352200 · 12352200
- Safety Statements
- 22 · 22-24/25
- WGK Germany
- 3 · 3
- Storage Class
- 11 · 11 - Combustible Solids
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
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
DescriptionFTase inhibitor I is a potent inhibitor of farnesyltransferase (FTase; IC50 = 21 nM) that is greater than 30-fold selective for FTase over geranylgeranyl transferase (GGTase; IC50 = 790 nM). It prevents farnesylation of Ras and inhibits proliferation of cells transformed by Ras farnesylation. In a dog model of subarachnoid hemorrhage, it reduces GTP-Ras in spastic basilar arteries, decreases angiographic vasospasm, and improves clinical scores.
UsesFTase Inhibitor I is a potent, selective, peptidomimetic FTase inhibitor.
Additional notes
DefinitionChEBI: A dipeptide obtained from the tetrapeptide Cys-Val-Phe-Met by reduction of the amide carbonyl groups of the Cys and Val residues.
Related reactions
0 records
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Compound notes
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