(2S)-2-[(2S)-2-[(2S)-2-[(2R)-2-amino-3-sulfanylpropanamido]-3-methylbutanamido]-3-(naphthalen-2-yl)propanamido]-4-(methylsulfanyl)butanoic acid

• ChemBase ID: 131055
• Molecular Formular: C26H36N4O5S2
• Molecular Mass: 548.71784
• Monoisotopic Mass: 548.21271227
• SMILES: CC(C)[C@@H](C(=O)N[C@@H](Cc1ccc2ccccc2c1)C(=O)N[C@@H](CCSC)C(=O)O)NC(=O)[C@H](CS)N
• Canonical SMILES: CSCC[C@@H](C(=O)O)NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CS)N)Cc1ccc2c(c1)cccc2
• InChI: InChI=1S/C26H36N4O5S2/c1-15(2)22(30-23(31)19(27)14-36)25(33)29-21(24(32)28-20(26(34)35)10-11-37-3)13-16-8-9-17-6-4-5-7-18(17)12-16/h4-9,12,15,19-22,36H,10-11,13-14,27H2,1-3H3,(H,28,32)(H,29,33)(H,30,31)(H,34,35)/t19-,20-,21-,22-/m0/s1
• InChIKey: HZPSWNVHTKOMLQ-CMOCDZPBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-[(2R)-2-amino-3-sulfanylpropanamido]-3-methylbutanamido]-3-(naphthalen-2-yl)propanamido]-4-(methylsulfanyl)butanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-[(2R)-2-amino-3-sulfanylpropanamido]-3-methylbutanamido]-3-(naphthalen-2-yl)propanamido]-4-(methylsulfanyl)butanoic acid
• Synonyms: Cys-Val-2-Nal-Met

Database IDs

• CAS Number: 158022-12-9
• MDL Number: MFCD00798743
• PubChem SID: 162225333
• PubChem CID: 44382767

CALCULATED PROPERTIES

• Acid pKa: 3.547424
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): -0.21910171
• LogD (pH = 7.4): -0.35485002
• Log P: -0.2209722
• Molar Refractivity: 147.2693 cm^3
• Polarizability: 59.077435 Å^3
• Polar Surface Area: 150.62 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)

DETAILS

Sigma Aldrich - C4433

Amino Acid Sequence
Cys-Val-Ala(2-naphthyl)-Met
Biochem/physiol Actions
p21ras farnesyltransferase inhibitor. While many tetrapeptide "inhibitors" of p21ras FTase are known, most act instead as competitive substrates. This compound is not farnesylated and is thus a true inhibitor.1