Myriocin

Modify Date: 2024-01-02 10:43:15

Myriocin Structure
Myriocin structure
 Common Name Myriocin
CAS Number 35891-70-4 Molecular Weight 401.538
Density 1.1±0.1 g/cm3 Boiling Point 636.7±55.0 °C at 760 mmHg
Molecular Formula C21H39NO6 Melting Point N/A
MSDS Chinese USA Flash Point 338.8±31.5 °C
Symbol GHS06
GHS06		 Signal Word Danger

 Use of Myriocin


Myriocin, a fungal metabolite isolated from Myriococcum albomyces, Isaria sinclairi and Mycelia sterilia, is a potent inhibitor of serine-palmitoyl-transferase (SPT) and a key enzyme in de novo synthesis of sphingolipids[1]. Myriocin strongly suppresses replication of both the subgenomic HCV-1b replicon and the JFH-1 strain of genotype 2a infectious HCV[2], with an IC50 of 3.5 µg/mL for inhibiting HCV infection[3].

 Names

Name myriocin
Synonym More Synonyms

 Myriocin Biological Activity

Description Myriocin, a fungal metabolite isolated from Myriococcum albomyces, Isaria sinclairi and Mycelia sterilia, is a potent inhibitor of serine-palmitoyl-transferase (SPT) and a key enzyme in de novo synthesis of sphingolipids[1]. Myriocin strongly suppresses replication of both the subgenomic HCV-1b replicon and the JFH-1 strain of genotype 2a infectious HCV[2], with an IC50 of 3.5 µg/mL for inhibiting HCV infection[3].
Related Catalog
Target

Serine-palmitoyl-transferase (SPT)[1]

References

[1]. He Q, et al. Inhibition of serine palmitoyltransferase by myriocin, a natural mycotoxin, causes inductionof c-myc in mouse liver. Mycopathologia. 2004 Apr;157(3):339-47.

[2]. Amemiya F, et al. Targeting lipid metabolism in the treatment of hepatitis C virus infection. J Infect Dis. 2008 Feb 1;197(3):361-70.

[3]. Ciesek S, et al. The suppressive effect that myriocin has on hepatitis C virus RNA replication is independent of inhibition of serine palmitoyl transferase. J Infect Dis. 2008 Oct 1;198(7):1091-3.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 636.7±55.0 °C at 760 mmHg
Molecular Formula C21H39NO6
Molecular Weight 401.538
Flash Point 338.8±31.5 °C
Exact Mass 401.277740
PSA 141.08000
LogP 4.21
Vapour Pressure 0.0±4.3 mmHg at 25°C
Index of Refraction 1.522
Storage condition -20℃

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
JX3890000
CHEMICAL NAME :
6-Eicosenoic acid, 2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-, (2S-(2R*,3S*,4S*,6E))-
CAS REGISTRY NUMBER :
35891-70-4
LAST UPDATED :
198910
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C21-H39-N-O6
MOLECULAR WEIGHT :
401.61
WISWESSER LINE NOTATION :
Q1XZVQYQYQ2U7V6

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2 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: 25,109,1972
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: 25,109,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5 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: 25,109,1972
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
250 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
85ERAY "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978 Volume(issue)/page/year: 3,2067,1978

 Safety Information

Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301
Precautionary Statements P301 + P310
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes Xi; Xn
Risk Phrases 22
RIDADR UN 2811 6.1/PG 3
WGK Germany 3.0
RTECS JX3890000
Hazard Class 6.1

 Synthetic Route

 Articles70

More Articles
Fungal metabolite myriocin promotes human herpes simplex virus-2 infection.

Life Sci. 120 , 31-8, (2015)

Myriocin is a fungal metabolite with antiviral activity, including influenza, hepatitis B, and hepatitis C viruses. We investigated whether myriocin has activity against human HSV-2, one of the most p...

Phosphorylation of caveolin-1 on tyrosine-14 induced by ROS enhances palmitate-induced death of beta-pancreatic cells.

Biochim. Biophys. Acta 1852(5) , 693-708, (2015)

A considerable body of evidence exists implicating high levels of free saturated fatty acids in beta pancreatic cell death, although the molecular mechanisms and the signaling pathways involved have n...

Ceramide metabolism regulates autophagy and apoptotic cell death induced by melatonin in liver cancer cells.

J. Pineal Res. 59 , 178-89, (2015)

Autophagy is a process that maintains homeostasis during stress, although it also contributes to cell death under specific contexts. Ceramides have emerged as important effectors in the regulation of ...

 Synonyms

Thermozymocidin
ISP-1
6-Eicosenoic acid, 2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-, (2S,3R,4R,6E)-
(2S,3R,4R,6E)-2-Amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxo-6-icosenoic acid
D-Serine, 2-[(1R,2R,4E)-1,2-dihydroxy-12-oxo-4-octadecen-1-yl]-
ISP-I
Myriocin from Mycelia sterilia
MFCD01632772
Myriocin
Myriocin,Mycelia sterilia
antibiotic ISP-I
(E,2S,3R,4R)-2-amino-3,4-dihydroxy-2-(hydroxymethyl)-14-oxoicos-6-enoic acid
2-[(1R,2R,4E)-1,2-Dihydroxy-12-oxo-4-octadecen-1-yl]-D-serine
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