sodium (6R)-6-[(3R,4R,6R)-4-(hydrogen phosphonatooxy)-3,6,13-trihydroxy-3-methyltrideca-1,7,9,11-tetraen-1-yl]-5,6-dihydro-2H-pyran-2-one

• ChemBase ID: 155484
• Molecular Formular: C19H26NaO9P
• Molecular Mass: 452.367871
• Monoisotopic Mass: 452.12121332
• SMILES: CC(C=C[C@H]1CC=CC(=O)O1)([C@@H](C[C@H](/C=C/C=C/C=C/CO)O)OP(=O)(O)[O-])O.[Na+]
• Canonical SMILES: OC/C=C/C=C/C=C/[C@@H](C[C@H](C(C=C[C@H]1CC=CC(=O)O1)(O)C)OP(=O)(O)[O-])O.[Na+]
• InChI: InChI=1S/C19H27O9P.Na/c1-19(23,12-11-16-9-7-10-18(22)27-16)17(28-29(24,25)26)14-15(21)8-5-3-2-4-6-13-20;/h2-8,10-12,15-17,20-21,23H,9,13-14H2,1H3,(H2,24,25,26);/q;+1/p-1/t15-,16+,17+,19+;/m0./s1
• InChIKey: XBUIKNRVGYFSHL-UVHBEQOXSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (6R)-6-[(3R,4R,6R)-4-(hydrogen phosphonatooxy)-3,6,13-trihydroxy-3-methyltrideca-1,7,9,11-tetraen-1-yl]-5,6-dihydro-2H-pyran-2-one
• IUPAC Traditional name: sodium (6R)-6-[(3R,4R,6R)-4-(hydrogen phosphonatooxy)-3,6,13-trihydroxy-3-methyltrideca-1,7,9,11-tetraen-1-yl]-5,6-dihydropyran-2-one
• Synonyms: Fostriecin sodium salt from Streptomyces pulveraceus

Database IDs

• CAS Number: 87860-39-7
• MDL Number: MFCD09971059
• PubChem SID: 24894863; 162249622
• PubChem CID: 71312142

CALCULATED PROPERTIES

• Acid pKa: 1.5337106
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.7715089
• LogD (pH = 7.4): -2.630004
• Log P: 0.6297701
• Molar Refractivity: 110.3816 cm^3
• Polarizability: 41.322952 Å^3
• Polar Surface Area: 156.58 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: UQ0600000
• 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: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H26NaO9P

DETAILS

Sigma Aldrich - F4425

Packaging
Packaged under argon.
Biochem/physiol Actions
Fostriecin was discovered as an anti-tumor antibiotic isolated from the fermentation beer of Streptomyces pulveraceus (subspecies fostreus). Fostriecin has antitumor activity against a wide spectrum of tumor cells in vitro and excellent activity against P388 and L1210 leukemias in vivo. The antitumor activity of fostriecin originates from its ability to interfere with the reversible phosphorylation of proteins that are critical for progression through the cell cycle.