Basic information
- CAS
12772-57-5- Standard SMILES
CC1CC2OC2/C=C\C=C\C(=O)Cc2c(Cl)c(O)cc(O)c2C(=O)O1- InChIKey
WYZWZEOGROVVHK-HZDAAVBUSA-N- Molecular formula
- C18H17ClO6
- Average molar mass
- 364.8 g/mol
- Monoisotopic mass
- 364.071366
Names & identifiers
- Preferred name
- Monorden (B117339F008)
- IUPAC
- (9Z,11E)-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
- English name
- RADICICOL
- Molecular formula
- C18H17ClO6
- Molecular weight
- 364.78
Names & synonyms
MONORDEN (B117339F008)SCHEMBL110205SCHEMBL31002997AKOS030213143BS-1397Radicicol; Radisicol; Monordene; Monorden; RHI-12648; FO-4910(2Z,4E)-8-chloro-9,11-dihydroxy-14-methyl-1a,14,15,15a-tetrahydro-6H-oxireno[e][2]benzoxacyclotetradecine-6,12(7H)-dioneMONORDENKF9-AKF58332FO-4910RADICICOL
Show more names
RADISICOLRHI-12648MONORODENEmonorderneNsc 294404
Database identifiers
- CAS
12772-57-5- PubChem CID
- 5359013
- DTXSID
DTXSID2042692
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 96.4 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 0
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 588
Physicochemical properties
- Melting point
- 193.5 ° · 193.5°
- alpha
- 20 · D20 +203° (chloroform)
- Boiling point
- 656.2 · 656.2±55.0 °C(Predicted)
- Density
- 1.364 · 1.364±0.06 g/cm3(Predicted)
- storage temp.
- 20 °C · −20°C
- solubility
- 10 mg/mL · ethanol: 10 mg/mL
- form
- solid
- pka
- 6.29 · 6.29±0.40(Predicted)
- color
- yellow
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
- 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+
- InChIKey
- WYZWZEOGROVVHK-ZUVMSYQZSA-N
- SMILES
- Clc1c2c(c(cc1O)O)C(=O)OC(CC3OC3\C=C\C=C\C(=O)C2)C
- FDA UNII
- 60 EH8GECX · I60EH8GECX
- UNSPSC Code
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 1
- rtecs
- RR1105000
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 29322090
- Toxicity
- mouse,LD50,intravenous,175mg/kg (175mg/kg),"CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 2, Pg. 448, 1980.
- risk_code
- 22-36/37/38-46-45
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- hazard_code
- Xn,T
- safety_code
- 26-45-53
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H301-H340-H350
- Hazard Classifications
- Acute Tox. 3 Oral
- Precautionary statements
- P202-P264-P270-P280-P301+P310-P405
Chemistry & industry
Applications
DescriptionRadicicol (12772-57-5) inhibits heat shock protein 90 (HSP90) activity by binding to the ATP-binding pocket.1In cells HSP90 client proteins such as Raf kinase2, HIF-1α3and estrogen receptor4are destabilized and proteolytically degraded. Radicicol inhibits expression of COX-2 without affecting COX-1 expression in LPS-stimulated macrophages (IC50=27 nM).5Inhibits angiogenesis.6
UsesRadicicol is a resorcylic acid lactone, produced by several fungal species, that exhibits broad spectrum antifungal and antitumour activity. Radicicol has been the subject of extensive investigation and inhibits protein tyrosine kinase, induces the differentiation of HL-60 cells into macrophages, blocks cell cycle at G1 and G2, 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 plasminogen activator production by vascular endothelial cells.
UsesRadicicol is an antitumor antibiotic, which inhibits the Hsp90 molecular chaperone.
UsesRadicicol from Diheterospora chlamydosporia has been used as an inhibitor of heat shock protein 90 (Hsp90):to study its effects on lifespan extension and health in Caenorhabditis elegansto study its effects on protein aggregation in yeast to study its effects on xanthone sensitized cancer cells
Suppliers48 total
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
上海哲研生物科技有限公司021-18017610038 18017610038 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
上海赛可锐生物科技有限公司
Related reactions
0 records
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Compound notes
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