(1R)-1-[(2S,3S)-3-{2-[(2S,3S)-3-[(1R)-1-hydroxyethyl]oxiran-2-yl]ethenyl}oxiran-2-yl]prop-2-en-1-ol

• ChemBase ID: 153730
• Molecular Formular: C11H16O4
• Molecular Mass: 212.24234
• Monoisotopic Mass: 212.10485899
• SMILES: C[C@H]([C@H]1[C@@H](O1)C=C[C@H]1[C@@H](O1)[C@@H](C=C)O)O
• Canonical SMILES: C=C[C@H]([C@@H]1O[C@H]1C=C[C@@H]1O[C@H]1[C@H](O)C)O
• InChI: InChI=1S/C11H16O4/c1-3-7(13)11-9(15-11)5-4-8-10(14-8)6(2)12/h3-13H,1H2,2H3/t6-,7-,8+,9+,10+,11+/m1/s1
• InChIKey: DLVJMFOLJOOWFS-VCACHIOZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R)-1-[(2S,3S)-3-{2-[(2S,3S)-3-[(1R)-1-hydroxyethyl]oxiran-2-yl]ethenyl}oxiran-2-yl]prop-2-en-1-ol
• IUPAC Traditional name: (1R)-1-[(2S,3S)-3-{2-[(2S,3S)-3-[(1R)-1-hydroxyethyl]oxiran-2-yl]ethenyl}oxiran-2-yl]prop-2-en-1-ol
• Synonyms: 4,5:8,9-Dianhydro-1,2,6,7,11-pentadeoxy-D-threo-D-ido-undeca-1,6-dienitol; (-)-Depudecin

Database IDs

• CAS Number: 139508-73-9
• MDL Number: MFCD04039998
• PubChem SID: 162247869; 24893973
• PubChem CID: 71311723

CALCULATED PROPERTIES

• Acid pKa: 13.665458
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.32819587
• LogD (pH = 7.4): 0.32819566
• Log P: 0.3281959
• Molar Refractivity: 54.9537 cm^3
• Polarizability: 21.70933 Å^3
• Polar Surface Area: 65.52 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: liquid

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)
• Biological Source: from microbial
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C11H16O4

DETAILS

Sigma Aldrich - D5816

Biochem/physiol Actions
Inhibitor of histone deacetylase (HDAC) both in vivo and in vitro. Alters the spindle shaped morphology of v-Ha-ras-transformed NIH3T3 cells to a flattened shape and induces an intricate actin stress fiber network in these cells and in MG63 osteosarcoma cells. Also exhibits anti-angiogenic activity.