methyl (3S)-3-[(2S,3R)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}propanamido]-3-hydroxypropanamido]-3-hydroxybutanamido]-5-fluoro-4-oxopentanoate

• ChemBase ID: 106526
• Molecular Formular: C24H33FN4O10
• Molecular Mass: 556.5380232
• Monoisotopic Mass: 556.2180715
• SMILES: COC(=O)C[C@H](NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](C)NC(=O)OCc1ccccc1)[C@@H](C)O)C(=O)CF
• Canonical SMILES: COC(=O)C[C@@H](C(=O)CF)NC(=O)[C@H]([C@H](O)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)OCc1ccccc1)C)CO
• InChI: InChI=1S/C24H33FN4O10/c1-13(26-24(37)39-12-15-7-5-4-6-8-15)21(34)28-17(11-30)22(35)29-20(14(2)31)23(36)27-16(18(32)10-25)9-19(33)38-3/h4-8,13-14,16-17,20,30-31H,9-12H2,1-3H3,(H,26,37)(H,27,36)(H,28,34)(H,29,35)/t13-,14+,16-,17-,20-/m0/s1
• InChIKey: LICIOVKJUZZCAM-ACSCVQKFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (3S)-3-[(2S,3R)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}propanamido]-3-hydroxypropanamido]-3-hydroxybutanamido]-5-fluoro-4-oxopentanoate
• IUPAC Traditional name: methyl (3S)-3-[(2S,3R)-2-[(2S)-2-[(2S)-2-{[(benzyloxy)carbonyl]amino}propanamido]-3-hydroxypropanamido]-3-hydroxybutanamido]-5-fluoro-4-oxopentanoate
• Synonyms: Z-Ala-Ser-Thr-Asp(OMe)-FMK; Z-ASTD(OMe)-FMK; Z-Ala-Ser-Thr-Asp(OMe)-Fluoromethylketone; EMAP II inhibitor; Z-Ala-Ser-Thr-Asp(OMe)-fluoromethyl ketone

Database IDs

• MDL Number: MFCD03453606
• PubChem SID: 162105586
• PubChem CID: 5497180

CALCULATED PROPERTIES

• Acid pKa: 11.0833235
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -1.795352
• LogD (pH = 7.4): -1.7954308
• Log P: -1.7953509
• Molar Refractivity: 129.9414 cm^3
• Polarizability: 51.16657 Å^3
• Polar Surface Area: 209.46 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: solid

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% (TLC)
• Empirical Formula (Hill Notation): C24H33N4O10F

DETAILS

MP Biomedicals - 03FK031

An inhibitor for EMAP-II.

Sigma Aldrich - C9359

Amino Acid Sequence
Z-Ala-Ser-Thr-Asp(OMe)-FMK
Biochem/physiol Actions
Cell-permeable inhibitor of endothelial monocyte-activating polypeptide II (EMAP-II).

REFERENCES

• Knies, U. et al., Proc. Natl. Acad. Sci., 95:12322 (1998).