Chaetocin

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Names

[ Name ]:
Chaetocin

[Synonym ]:
(3S,3'S)-3,3'-bis-hydroxymethyl-2,2'-dimethyl-(5at,10bt,5'at',10'bt')-2,3,5a,6,2',3',5'a,6'-octahydro-[10b,10'b]bi[3r,11ac-epidisulfano-pyrazino[1',2':1,5]pyrrolo[2,3-b]indolyl]-1,4,1',4'-tetraone
(+)-chaetocin A
(1S,1'S,3R,3'R,11R,11'R,14S,14'S)-14,14'-Bis(hydroxymethyl)-18,18'-dimethyl-3,3'-bi(15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0.0.0]octadecane)-4,4',6,6',8,8'-hexaene-13,13',17,17 ;'-tetrone
'bR,11aS,11'aS)
Chetocin

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Molecular Formula ]:
C₃₀H₂₈N₆O₆S₄

[ Molecular Weight ]:
696.840

[ Exact Mass ]:
696.095337

[ PSA ]:
246.96000

[ LogP ]:
3.10

[ Index of Refraction ]:
1.930

[ Storage condition ]:
2~8°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FM3032000

CHEMICAL NAME :: Chetocin

CAS REGISTRY NUMBER :: 28097-03-2

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C30-H28-N6-O6-S4

MOLECULAR WEIGHT :: 696.88

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 :: 1200 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: 4(1),170,1980

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1700 ug/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: 4(1),170,1980

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302 + H312 + H332

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
20/21/22

[ RIDADR ]:
UN 1544

[ RTECS ]:
FM3032000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Inhibition of histone H3K9 methyltransferases by gliotoxin and related epipolythiodioxopiperazines.

J. Antibiot. 65(5) , 263-5, (2012)

Individual epigenetic status of the pathogenic D4Z4 macrosatellite correlates with disease in facioscapulohumeral muscular dystrophy.

Clin. Epigenetics. 7(1) , 37, (2015)

Both forms of facioscapulohumeral muscular dystrophy (FSHD) are associated with aberrant epigenetic regulation of the chromosome 4q35 D4Z4 macrosatellite. Chromatin changes due to large deletions of h...

Epidithiodiketopiperazine as a pharmacophore for protein lysine methyltransferase G9a inhibitors: reducing cytotoxicity by structural simplification.

Bioorg. Med. Chem. Lett. 23(3) , 733-6, (2013)

Chaetocin (1), a structurally complex epidithiodiketopiperazine (ETP) alkaloid produced by Chaetomium minutum, is a potent inhibitor of protein lysine methyltransferase G9a, which plays important role...