(3S)-4-(benzylsulfanyl)-3-[(2S)-2-[(2S)-2-{[(tert-butoxy)carbonyl]amino}propanamido]propanamido]-4-oxobutanoic acid

• ChemBase ID: 106674
• Molecular Formular: C22H31N3O7S
• Molecular Mass: 481.56244
• Monoisotopic Mass: 481.18827135
• SMILES: C[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(=O)O)C(=O)SCc1ccccc1
• Canonical SMILES: OC(=O)C[C@@H](C(=O)SCc1ccccc1)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OC(C)(C)C)C)C
• InChI: InChI=1S/C22H31N3O7S/c1-13(23-18(28)14(2)24-21(31)32-22(3,4)5)19(29)25-16(11-17(26)27)20(30)33-12-15-9-7-6-8-10-15/h6-10,13-14,16H,11-12H2,1-5H3,(H,23,28)(H,24,31)(H,25,29)(H,26,27)/t13-,14-,16-/m0/s1
• InChIKey: FASYOWNBLQCNGJ-DZKIICNBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-4-(benzylsulfanyl)-3-[(2S)-2-[(2S)-2-{[(tert-butoxy)carbonyl]amino}propanamido]propanamido]-4-oxobutanoic acid
• IUPAC Traditional name: (3S)-4-(benzylsulfanyl)-3-[(2S)-2-[(2S)-2-[(tert-butoxycarbonyl)amino]propanamido]propanamido]-4-oxobutanoic acid
• Synonyms: Boc-Ala-Ala-Asp-Thiobenzyl Ester; Boc-AAD-Thiobenzyl Ester; Boc-Ala-Ala-Asp-Thiobenzyl Ester; BAADT; Boc-Ala-Ala-Asp-S-Bzl; Boc-Ala-Ala-Asp thiobenzyl ester

Database IDs

• MDL Number: MFCD00151860
• PubChem SID: 162087696
• PubChem CID: 25108819

CALCULATED PROPERTIES

• Acid pKa: 3.9972324
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 0.20761576
• LogD (pH = 7.4): -1.4409124
• Log P: 1.7197549
• Molar Refractivity: 121.7271 cm^3
• Polarizability: 47.921444 Å^3
• Polar Surface Area: 150.9 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble20 mM
• Apperance: white powder

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: ≥97% (HPLC)

DETAILS

MP Biomedicals - 03SB028

A colorimetric substrate for Granzyme B.

Sigma Aldrich - B5305

Application
Colorimetric substrate for granzyme B.
Caution
Very Hygroscopic

REFERENCES

• Poe, M. et al., J. Biol. Chem., 226(1):98 (1991).
• Odake, S. et al., Biochem., 30:2217 (1991).