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Shikalkin

Names

[ CAS No. ]:
23444-65-7

[ Name ]:
Shikalkin

[Synonym ]:
SHIKALKIN
5,8-Dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)-1,4-naphthoquinone
1,4-Naphthalenedione, 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-penten-1-yl)-
Arnebin-4
Alkannin
(±)-Alkannin
5,8-Dihydroxy-2-(1-hydroxy-4-methyl-3-penten-1-yl)-1,4-naphthoquinone
5,8-dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione

Biological Activity

[Description]:

Alkannin is a potent and specific inhibitor of tumor-specific pyruvate kinase-M2 (PKM2). Alkannin does not inhibit PKM1 and pyruvate kinase-L (PKL). Alkannin acts as a potential anticancer agent[1].

[Related Catalog]:

Research Areas >> Cancer
Research Areas >> Inflammation/Immunology
Signaling Pathways >> GPCR/G Protein >> Ras

[In Vitro]

Alkannin is a potent and specific inhibitor to PKM2, an enzyme that dictates the last rate-limiting step of glycolysis, which is essential for cancer cells’ proliferation and survival. In the absence of D-fructose-1,6-bisphosphate (FBP), the IC50 of Alkannin is 0.3 μM. In the presence of FBP (125 μM), the IC50 of Alkannin is 0.9 μM, respectively. Alkannin effectively inhibits the cellular glycolytic flux in cancer cells dominantly expressing PKM2[1]. Alkannin (2.5-20 μM, 1 hour) inhibit the rates of cellular lactate production and glucose consumption[1]. Western Blot Analysis[1] Cell Line: MCF-7 and A549 express PKM2 but not PKM1 and PKL Concentration: 0-20 μM Incubation Time: 1 hour Result: Inhibited the cellular glycolytic rate in a concentration-dependent manner.

[References]

[1]. J Chen, et al. Shikonin and its analogs inhibit cancer cell glycolysis by targeting tumor pyruvate kinase-M2. Oncogene. 2011 Oct 20;30(42):4297-306.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
567.4±50.0 °C at 760 mmHg

[ Melting Point ]:
149°C

[ Molecular Formula ]:
C16H16O5

[ Molecular Weight ]:
288.295

[ Flash Point ]:
311.0±26.6 °C

[ Exact Mass ]:
288.099762

[ PSA ]:
94.83000

[ LogP ]:
4.35

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.642

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
QL8000000
CHEMICAL NAME :
1,4-Naphthoquinone, 5,8-dihydroxy-6-(1-hydroxy-4-methyl-3-pentenyl)-, (-)-
CAS REGISTRY NUMBER :
23444-65-7
BEILSTEIN REFERENCE NO. :
3213296
LAST UPDATED :
199801
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C16-H16-O5
MOLECULAR WEIGHT :
288.32
WISWESSER LINE NOTATION :
L66 BV EVJ CYQ2YU1&1 GQ JQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NAHRAR Nahrung. Chemistry, Biochemistry, Microbiology, Technology, Nutrition. (Akademie-Verlag GmBH, Postfach 1233, Berlin DDR-1086, Ger. Dem. Rep.) V.1- 1957- Volume(issue)/page/year: 15,505,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NAHRAR Nahrung. Chemistry, Biochemistry, Microbiology, Technology, Nutrition. (Akademie-Verlag GmBH, Postfach 1233, Berlin DDR-1086, Ger. Dem. Rep.) V.1- 1957- Volume(issue)/page/year: 15,505,1971

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
22

[ Safety Phrases ]:
22-24/25

[ HS Code ]:
2914690090

Customs

[ HS Code ]: 2914690090

[ Summary ]:
2914690090 other quinones。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:5.5%。General tariff:30.0%

Related Compounds

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