Usnic acid

Names

[ Name ]:
Usnic acid

[Synonym ]:
Usnic acid
EINECS 231-456-0
(+)-Usniacin
(9bR)-2,6-Diacetyl-1,7,9-trihydroxy-8,9b-dimethyldibenzo[b,d]furan-3(9bH)-one
3(9bH)-Dibenzofuranone, 2,6-diacetyl-1,7,9-trihydroxy-8,9b-dimethyl-, (9bR)-
MFCD00016878
D-Usnic acid

Biological Activity

[Description]:

(+)-Usnic acid is isolated from isolated from lichens, binds at the ATP-binding pocket of mTOR, and inhibits mTORC1/2 activity. (+)-Usnic acid inhibits the phosphorylation of mTOR downstream effectors: Akt (Ser473), 4EBP1, S6K, induces autophay, with anti-cancer activity[1].

[Related Catalog]:

Signaling Pathways >> PI3K/Akt/mTOR >> mTOR

Research Areas >> Cancer

[Target]

mTORC1

mTORC2

[References]

[1]. Ebrahim HY, et al. Usnic Acid Benzylidene Analogues as Potent Mechanistic Target of Rapamycin Inhibitors for the Control of Breast Malignancies. J Nat Prod. 2017 Apr 28;80(4):932-952.

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Boiling Point ]:
638.2±55.0 °C at 760 mmHg

[ Melting Point ]:
201-203 °C(lit.)

[ Molecular Formula ]:
C₁₈H₁₆O₇

[ Molecular Weight ]:
344.315

[ Flash Point ]:
236.0±25.0 °C

[ Exact Mass ]:
344.089600

[ PSA ]:
121.13000

[ LogP ]:
2.30

[ Vapour Pressure ]:
0.0±2.0 mmHg at 25°C

[ Index of Refraction ]:
1.679

[ Storage condition ]:
2~8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HP5295050

CHEMICAL NAME :: 3(9bH)-dibenzofuranone, 2,6-diacetyl-1,7,9-trihydroxy-8,9b-dimethyl-, D-

CAS REGISTRY NUMBER :: 7562-61-0

LAST UPDATED :: 198910

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C18-H16-O7

MOLECULAR WEIGHT :: 344.34

WISWESSER LINE NOTATION :: T B656 EV HO BHJ B1 CQ DV1 JV1 KQ L1 MQ

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 :: 838 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TAKHAA Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. (Takeda Yakuhin Kogyo K.K., 2-17-85 Jusohon-machi, Yodogawa-ku, Osaka 532, Japan) V.29- 1970- Volume(issue)/page/year: 31,247,1972 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1500 ug/kg

SEX/DURATION :: female 1 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - female fertility index (e.g. # females pregnant per # sperm positive females; # females pregnant per # females mated)

REFERENCE :: NATUAS Nature. (Nature Subscription Dept., POB 1018, Manasguan, NJ 08736) V.1- 1869- Volume(issue)/page/year: 176,249,1955

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

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

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R22

[ Safety Phrases ]:
S36

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
HP5295050

[ HS Code ]:
2917399090

Customs

[ HS Code ]: 2917399090

[ Summary ]:
2917399090 aromatic polycarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

Articles

Proton-shuttling lichen compound usnic acid affects mitochondrial and lysosomal function in cancer cells.

PLoS ONE 7 , e51296, (2012)

The lichen compound usnic acid (UA) is a lipophilic weak acid that acts as a proton shuttle and causes loss of mitochondrial inner membrane potential. In the current study we show that UA treatment in...

Related Compounds

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