bis((2S)-N-[(1S)-1-{[(2S)-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-3-methylbutyl]-2-acetamido-4-methylpentanamide); sulfuric acid

• ChemBase ID: 132914
• Molecular Formular: C40H78N12O12S
• Molecular Mass: 951.18552
• Monoisotopic Mass: 950.558287
• SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C=O)NC(=O)C.CC(C)C[C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(=N)N)C=O)NC(=O)C.OS(=O)(=O)O
• Canonical SMILES: OS(=O)(=O)O.O=C[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)CC(C)C)CC(C)C)CCCNC(=N)N.O=C[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)C)CC(C)C)CC(C)C)CCCNC(=N)N
• InChI: InChI=1S/2C20H38N6O4.H2O4S/c2*1-12(2)9-16(24-14(5)28)19(30)26-17(10-13(3)4)18(29)25-15(11-27)7-6-8-23-20(21)22;1-5(2,3)4/h2*11-13,15-17H,6-10H2,1-5H3,(H,24,28)(H,25,29)(H,26,30)(H4,21,22,23);(H2,1,2,3,4)/t2*15-,16-,17-;/m00./s1
• InChIKey: CIPMKIHUGVGQTG-VFFZMTJFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis((2S)-N-[(1S)-1-{[(2S)-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-3-methylbutyl]-2-acetamido-4-methylpentanamide); sulfuric acid
• IUPAC Traditional name: bis((2S)-N-[(1S)-1-{[(2S)-5-carbamimidamido-1-oxopentan-2-yl]carbamoyl}-3-methylbutyl]-2-acetamido-4-methylpentanamide); sulfuric acid
• Synonyms: N-Acetyl-L-leucyl-L-leucyl-L-argininal hemisulfate salt; Acetyl-Leu-Leu-Arg-al; Leupeptin hemisulfate salt; N-乙酰基-L-亮氨酰-L-亮氨酰-L-精氨醛 半硫酸盐; 亮抑酶肽 半硫酸盐

Database IDs

• CAS Number: 103476-89-7
• MDL Number: MFCD00037012
• PubChem SID: 162227191; 24896420; 24882188; 24896328; 24896498
• PubChem CID: 2733491

CALCULATED PROPERTIES

• Acid pKa: 12.4916725
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -2.8089597
• LogD (pH = 7.4): -2.8059762
• Log P: -0.7743988
• Molar Refractivity: 124.3835 cm^3
• Polarizability: 44.33278 Å^3
• Polar Surface Area: 166.27 Å^2
• Rotatable Bonds: 28
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble10 mM (Solutions are stable for a week at 4 °C. Stock solutions are stable up to 6 months at -20 °C.); H2O: soluble50 mg/mL

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: ≥85% (HPLC); ≥90% (HPLC); ≥98% (HPLC)
• Biological Source: microbial; synthetic
• Quality Level: PREMIUM
• Product Line: BioUltra
• Linear Formula: C20H38N6O4 · 1/2H2SO4

DETAILS

Sigma Aldrich - L8511

Analysis Note
由于三种形式在溶液中达到平衡，亮抑酶肽可在 HPLC 上形成多个峰。通过三个主峰测定纯度。主要的杂质肽为外消旋亮抑酶肽。
Biochem/physiol Actions
Inhibitor of serine and cysteine proteases. Inhibits plasmin, trypsin, papain, calpain, and cathepsin B. Does not inhibit pepsin, cathepsins A and D, thrombin, or α-chymotrypsin. Effective concentration 10-100 μM. There have been numerous studies using leupeptin to protect against hearing loss caused by acoustic overstimulation or the ototoxic antibiotic gentamicin.1 (Loss of cochlear hair cells is believed to be mediated by calpain.)

Sigma Aldrich - 62070

Analysis Note
Leupeptin gives multiple peaks on HPLC due to equilibria among three forms in solution. Purity determined using three main peaks. Majority of contaminating peptide is racemized leupeptin.
Other Notes
Inhibitor of trypsin, plasmin, papain and cathepsin B2,3,4
Unit Definition
1 U corresponds to the amount of inhibitor which reduces the trypsin activity by 1 BAEE-U. (1 BAEE-U is the amount of enzyme which increases the absorbance at 253 nm by 0.001 per minute at pH 7.6 and 25 °C; BAEE, Fluka No. 12880, as substrate)
Biochem/physiol Actions
Inhibitor of serine and cysteine proteases. Inhibits plasmin, trypsin, papain, calpain, and cathepsin B. Does not inhibit pepsin, cathepsins A and D, thrombin, or α-chymotrypsin. Effective concentration 10-100 μM. There have been numerous studies using leupeptin to protect against hearing loss caused by acoustic overstimulation or the ototoxic antibiotic gentamicin.1 (Loss of cochlear hair cells is believed to be mediated by calpain.)

Sigma Aldrich - L2884

Analysis Note
由于三种形式在溶液中达到平衡，亮抑酶肽可在 HPLC 上形成多个峰。通过三个主峰测定纯度。主要的杂质肽为外消旋亮抑酶肽。
Biochem/physiol Actions
Inhibitor of serine and cysteine proteases. Inhibits plasmin, trypsin, papain, calpain, and cathepsin B. Does not inhibit pepsin, cathepsins A and D, thrombin, or α-chymotrypsin. Effective concentration 10-100 μM. There have been numerous studies using leupeptin to protect against hearing loss caused by acoustic overstimulation or the ototoxic antibiotic gentamicin.1 (Loss of cochlear hair cells is believed to be mediated by calpain.)

Sigma Aldrich - L5793

Analysis Note
Leupeptin gives multiple peaks on HPLC due to equilibria among three forms in solution. Purity determined using three main peaks. Majority of contaminating peptide is racemized leupeptin.
Biochem/physiol Actions
Inhibitor of serine and cysteine proteases. Inhibits plasmin, trypsin, papain, calpain, and cathepsin B. Does not inhibit pepsin, cathepsins A and D, thrombin, or α-chymotrypsin. Effective concentration 10-100 μM. There have been numerous studies using leupeptin to protect against hearing loss caused by acoustic overstimulation or the ototoxic antibiotic gentamicin.1 (Loss of cochlear hair cells is believed to be mediated by calpain.)