(4R,6R,8R,9Z,11Z)-16-chloro-17,19-dihydroxy-4-methyl-3,7-dioxatricyclo[13.4.0.06,8]nonadeca-1(15),9,11,16,18-pentaene-2,13-dione

• ChemBase ID: 132458
• Molecular Formular: C18H17ClO6
• Molecular Mass: 364.77698
• Monoisotopic Mass: 364.07136594
• SMILES: C[C@@H]1C[C@@H]2[C@H](O2)/C=C\C=C/C(=O)Cc2c(c(cc(c2Cl)O)O)C(=O)O1
• Canonical SMILES: C[C@@H]1C[C@H]2O[C@@H]2/C=C\C=C/C(=O)Cc2c(C(=O)O1)c(O)cc(c2Cl)O
• InChI: InChI=1S/C18H17ClO6/c1-9-6-15-14(25-15)5-3-2-4-10(20)7-11-16(18(23)24-9)12(21)8-13(22)17(11)19/h2-5,8-9,14-15,21-22H,6-7H2,1H3/b4-2-,5-3-/t9-,14-,15-/m1/s1
• InChIKey: WYZWZEOGROVVHK-WSGSENCDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,6R,8R,9Z,11Z)-16-chloro-17,19-dihydroxy-4-methyl-3,7-dioxatricyclo[13.4.0.0^6,^8]nonadeca-1(15),9,11,16,18-pentaene-2,13-dione
• IUPAC Traditional name: (4R,6R,8R,9Z,11Z)-16-chloro-17,19-dihydroxy-4-methyl-3,7-dioxatricyclo[13.4.0.0^6,^8]nonadeca-1(15),9,11,16,18-pentaene-2,13-dione
• Synonyms: Monorden; [1aS-(1aR*,2Z,4E,14*,15aR*)]-8-Chloro-1a,14,15,15a-tetrahydro-9,11-dihydroxy-14-methyl-6H-oxireno[e][2]benzoxacyclotetradecin-6,12(7H)-dione; Radicicol from Diheterospora chlamydosporia

Database IDs

• CAS Number: 12772-57-5
• MDL Number: MFCD06795865
• PubChem SID: 24899351; 162226735
• PubChem CID: 45933581

CALCULATED PROPERTIES

• Acid pKa: 7.022605
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 3.6637928
• LogD (pH = 7.4): 3.1545846
• Log P: 3.6765287
• Molar Refractivity: 93.5609 cm^3
• Polarizability: 35.18881 Å^3
• Polar Surface Area: 96.36 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble10 mg/mL
• Apperance: yellow solid

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 45-46-22-36/37/38
• Safety Statements: 53-26-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335-H340-H350
• GHS Precautionary statements: P201-P261-P301 + P310-P305 + P351 + P338-P308 + P313
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... HSP90AA1(3320), SRC(6714)rat ... Src(83805)

DETAILS

Sigma Aldrich - R2146

Biochem/physiol Actions
Antifungal macrolactone antibiotic that inhibits protein tyrosine kinase. Radicicol induces the differentiation of HL-60 cells into macrophages, blocking cell cycle at G1 and G2. It suppresses NIH 3T3 cell transformation by diverse oncogenes such as src, ras and mos and also suppresses the expression of mitogen-inducible cyclooxygenase-2. As a cell differentiation modulator, radicicol has anti-angiogenic activity in vivo, inhibiting the proliferation of and plasminogen activator production by vascular endothelial cells.
Caution
Photosensitive