N-[(1S)-2-hydroxy-1-{[(2S)-1-[(2R)-2-(hydroxymethyl)oxiran-2-yl]-4-methyl-1-oxopentan-2-yl]carbamoyl}ethyl]-6-methylheptanamide

• ChemBase ID: 154842
• Molecular Formular: C20H36N2O6
• Molecular Mass: 400.50964
• Monoisotopic Mass: 400.25733688
• SMILES: CC(C)CCCCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)[C@]1(CO1)CO
• Canonical SMILES: OC[C@@H](C(=O)N[C@H](C(=O)[C@]1(CO)OC1)CC(C)C)NC(=O)CCCCC(C)C
• InChI: InChI=1S/C20H36N2O6/c1-13(2)7-5-6-8-17(25)21-16(10-23)19(27)22-15(9-14(3)4)18(26)20(11-24)12-28-20/h13-16,23-24H,5-12H2,1-4H3,(H,21,25)(H,22,27)/t15-,16-,20+/m0/s1
• InChIKey: IUDBVFIQSSOIDB-TWOQFEAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(1S)-2-hydroxy-1-{[(2S)-1-[(2R)-2-(hydroxymethyl)oxiran-2-yl]-4-methyl-1-oxopentan-2-yl]carbamoyl}ethyl]-6-methylheptanamide
• IUPAC Traditional name: N-[(1S)-2-hydroxy-1-{[(2S)-1-[(2R)-2-(hydroxymethyl)oxiran-2-yl]-4-methyl-1-oxopentan-2-yl]carbamoyl}ethyl]-6-methylheptanamide
• Synonyms: Dihydroeponemycin

Database IDs

• CAS Number: 126463-64-7
• MDL Number: MFCD17215971
• PubChem SID: 162248980
• PubChem CID: 10092400

CALCULATED PROPERTIES

• Acid pKa: 12.207601
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): 1.258437
• LogD (pH = 7.4): 1.2584313
• Log P: 1.2584373
• Molar Refractivity: 104.0731 cm^3
• Polarizability: 41.336353 Å^3
• Polar Surface Area: 128.26 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥1 mg/mL
• Apperance: off-white to light tan powder
• Optical Rotation: [α]/D ±35.7°

Safety Information

• European Hazard Symbols: Harmful (Xn)
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H36N2O6

DETAILS

Sigma Aldrich - D4321

Biochem/physiol Actions
Dihydroeponemycin is an active derivative of eponemycin an antitumor antibiotic isolated from Streptomyces hygroscopicus. Dihydroeponemycin labels the catalytic threonine residues of the immunoproteasome subunits LMP2 and LMP7 and the constitutive proteasome subunit X, while epoxomicin covalently modifies the N-terminal catalytic threonine residues of the constitutive proteasome (X and Z) and immunoproteasome (LMP7 and MECL1) subunits.