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12772-57-5

12772-57-5 structure
12772-57-5 structure
  • Name: Radicicol
  • Chemical Name: radicicol
  • CAS Number: 12772-57-5
  • Molecular Formula: C18H17ClO6
  • Molecular Weight: 364.777
  • Catalog: API Antibiotics Other antibiotics
  • Create Date: 2018-04-19 08:00:00
  • Modify Date: 2024-01-02 22:42:08
  • Radicicol is an inhibitor of the ATPase/kinase with IC50 values of 1 μM, 100 μM and 400 μM, respectively for Hsp90, Topo VI and PDK3 [1]. Radicicol inhibits a wide variety of tumor cell lines by targeting Hsp90, binds to the ATPase domain of Hsp90 and prevents maturation of Hsp90 clients, leading to proteasomal degradation [2]. Radicicol is an antifungal antibiotic with antimalarial activity, impairs mitochondrial replication by targeting P. falciparum topoisomerase VIB[2]. Radicicol is an inhibitor of fat mass and obesity-associated protein (FTO), exhibits a dose-dependent inhibition of FTO demethylation activity with an IC50 value of 16.04 µM[3].

Name radicicol
Synonyms monorden
monorderne
[Biotinyl]-Radicicol
(1aR,2Z,4E,14R,15aR)-8-Chloro-9,11-dihydroxy-14-methyl-1a,14,15,15a-tetrahydro-6H-oxireno[e][2]benzoxacyclotetradecine-6,12(7H)-dione
Monorden/Radicicol
humicola fuscoatra
Radicicol from Diheterospora chlamydosporia
6H-Oxireno[e][2]benzoxacyclotetradecin-6,12(7H)-dione, 8-chloro-1a,14,15,15a-tetrahydro-9,11-dihydroxy-14-methyl-, (1aR,2Z,4E,14R,15aR)-
MFCD01709459
KF9-A
RADISICOL
Radicicol
[TAMRA]-Radicicol
MONORODENE
FO-4910
Description Radicicol is an inhibitor of the ATPase/kinase with IC50 values of 1 μM, 100 μM and 400 μM, respectively for Hsp90, Topo VI and PDK3 [1]. Radicicol inhibits a wide variety of tumor cell lines by targeting Hsp90, binds to the ATPase domain of Hsp90 and prevents maturation of Hsp90 clients, leading to proteasomal degradation [2]. Radicicol is an antifungal antibiotic with antimalarial activity, impairs mitochondrial replication by targeting P. falciparum topoisomerase VIB[2]. Radicicol is an inhibitor of fat mass and obesity-associated protein (FTO), exhibits a dose-dependent inhibition of FTO demethylation activity with an IC50 value of 16.04 µM[3].
Related Catalog
Target

IC50: of 1 μM (Hsp90), 100 μM (Topo VI) and 400 μM (PDK3)[1]

References

[1]. Kato M, et al. Distinct structural mechanisms for inhibition of pyruvate dehydrogenase kinase isoforms by AZD7545, dichloroacetate, and radicicol. Structure. 2007 Aug;15(8):992-1004. Epub 2007 Aug 2.

[2]. Chalapareddy S, et al. Radicicol confers mid-schizont arrest by inhibiting mitochondrial replication in Plasmodium falciparum. Antimicrob Agents Chemother. 2014 Aug;58(8):4341-52.

[3]. Wang R, et al. Identification of Natural Compound Radicicol as a Potent FTO Inhibitor. Mol Pharm. 2018 Sep 4;15(9):4092-4098.

Density 1.4±0.1 g/cm3
Boiling Point 656.2±55.0 °C at 760 mmHg
Melting Point 190-194ºC
Molecular Formula C18H17ClO6
Molecular Weight 364.777
Flash Point 350.7±31.5 °C
Exact Mass 364.071381
PSA 96.36000
LogP 1.53
Vapour Pressure 0.0±2.0 mmHg at 25°C
Index of Refraction 1.583
Storage condition -20°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RR1105000
CHEMICAL NAME :
6H-Oxireno(e)(2)benzoxacyclotetradecin-6,12(7H)-dione , 8-chloro-1a,14,15,15a-tetrahydro-9, 11-dihydroxy-14-methyl-
CAS REGISTRY NUMBER :
12772-57-5
LAST UPDATED :
199609
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C18-H17-Cl-O6
MOLECULAR WEIGHT :
364.80
WISWESSER LINE NOTATION :
T F3-14-6 BVO GO MV IU KUTT&J D1 PG QQ SQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 48,824,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
175 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 2,448,1980
Symbol GHS06 GHS08
GHS06, GHS08
Signal Word Danger
Hazard Statements H301-H340-H350
Precautionary Statements Missing Phrase - N15.00950417-P201-P280-P308 + P313
Hazard Codes Xn: Harmful;
Risk Phrases R22
Safety Phrases 26
RIDADR UN 2811 6.1/PG 3
WGK Germany 1
RTECS RR1105000
Hazard Class 6.1
HS Code 29322090