(2S,3S)-N-[(1S,2R)-2-hydroxy-1-{[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]carbamoyl}propyl]-3-methyl-2-[(2S,3S)-3-methyl-2-(N-methylacetamido)pentanamido]pentanamide

• ChemBase ID: 127272
• Molecular Formular: C28H50N4O7
• Molecular Mass: 554.7192
• Monoisotopic Mass: 554.36794996
• SMILES: O=C([C@@]1(C)CO1)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H]([C@@H](C)CC)N(C)C(=O)C)[C@H](O)C
• Canonical SMILES: CC[C@@H]([C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)[C@]1(C)OC1)CC(C)C)[C@H](O)C)NC(=O)[C@@H](N(C(=O)C)C)[C@H](CC)C)C
• InChI: InChI=1S/C28H50N4O7/c1-11-16(5)21(30-27(38)23(17(6)12-2)32(10)19(8)34)25(36)31-22(18(7)33)26(37)29-20(13-15(3)4)24(35)28(9)14-39-28/h15-18,20-23,33H,11-14H2,1-10H3,(H,29,37)(H,30,38)(H,31,36)/t16-,17-,18+,20-,21-,22-,23-,28+/m0/s1
• InChIKey: DOGIDQKFVLKMLQ-JTHVHQAWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-N-[(1S,2R)-2-hydroxy-1-{[(2S)-4-methyl-1-[(2R)-2-methyloxiran-2-yl]-1-oxopentan-2-yl]carbamoyl}propyl]-3-methyl-2-[(2S,3S)-3-methyl-2-(N-methylacetamido)pentanamido]pentanamide
• IUPAC Traditional name: epoxomicin
• Synonyms: BU 4061T; Epoxomicin; N-Acetyl-N-methyl-L-isoleucyl-L-isoleucyl-N-[(1S)-3-methyl-1-[[(2R)-2-methyloxiranyl]carbonyl]butyl]-L-threoninamide; Epoxomicin

Database IDs

• CAS Number: 134381-21-8
• MDL Number: MFCD03791061
• PubChem SID: 162221593
• PubChem CID: 11226684; 16760412
• CHEMBL: 207990
• Wikipedia Title: Epoxomicin

CALCULATED PROPERTIES

• Acid pKa: 11.898782
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 1.770858
• LogD (pH = 7.4): 1.7708464
• Log P: 1.7708585
• Molar Refractivity: 146.0534 cm^3
• Polarizability: 57.873833 Å^3
• Polar Surface Area: 157.44 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: 10 mg/mL in DMSO
• Apperance: solid; White 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: ≥95% (HPLC)

DETAILS

Sigma Aldrich - E3652

Biochem/physiol Actions
Epoxomicin, a natural product isolated from Actinomyces sp., is a cell-permeable, potent, selective and irreversible proteasome inhibitor.