CAS 12772-57-5|Radicicol

Introduction：Basic information about CAS 12772-57-5|Radicicol, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Radicicol BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles32
7. Synonyms

Common Name	Radicicol
CAS Number	12772-57-5	Molecular Weight	364.777
Density	1.4±0.1 g/cm3	Boiling Point	656.2±55.0 °C at 760 mmHg
Molecular Formula	C₁₈H₁₇ClO₆	Melting Point	190-194ºC
MSDS	ChineseUSA	Flash Point	350.7±31.5 °C
Symbol	GHS06, GHS08	Signal Word	Danger

Names

Name	radicicol
Synonym	More Synonyms

Radicicol BiologicalActivity

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	Signaling Pathways >>Apoptosis >>ApoptosisResearch Areas >>InfectionSignaling Pathways >>Membrane Transporter/Ion Channel >>ATP Synthase
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.

Chemical & Physical Properties

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
InChIKey	WYZWZEOGROVVHK-WSGSENCDSA-N
SMILES	CC1CC2OC2C=CC=CC(=O)Cc2c(Cl)c(O)cc(O)c2C(=O)O1
Storage condition	-20°C

Toxicological Information

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

Safety Information

Symbol	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

Articles32

Screening for negative effects of candidate ascidian antifoulant compounds on a target aquaculture species, Perna canaliculus Gmelin.

Biofouling 29(1) , 29-37, (2013)

The natural chemical compounds radicicol, polygodial and ubiquinone-10 (Q10) have previously been identified as inhibitors of metamorphosis in ascidian larvae. Accordingly, they have potential as a sp...

[Thermosensitization of tumor cells with inhibitors of chaperone activity and expression].

Biomed. Khim. 58(6) , 662-72, (2012)

Effects of inhibitors of the heat shock protein 90 (HSP90) chaperone activity and inhibitors of the heat shock protein (HSP) expression on sensitivity of HeLa tumor cells to hyperthermia were studied....

Geldanamycin and its derivatives as Hsp90 inhibitors.

Front. Biosci. (Landmark Ed.) 17 , 2269-77, (2012)

The Hsp90 molecule, one of the most abundant heat shock proteins in mammalian cells, maintains homeostasis and prevents stress-induced cellular damage. Hsp90 is expressed under normal conditions at a ...

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

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