Ikarugamycin

Names

[ Name ]:
Ikarugamycin

[Synonym ]:
14,17-Metheno-17H-as-indaceno[3,2-k][1,6]diazacycloheptadecine-9,16,18(1H)-trione, 3-ethyl-2,3,3a,5a,5b,6,10,11,12,13,14,15,20a,21,21a,21b-hexadecahydro-22-hydroxy-2-methyl-, (2R,3R,3aS,5aR,5bS,7Z,14S,19E,20aS,21aR,21bR)-
(3E,5S,7R,8R,10R,11R,12S,15R,16S,18Z,25S)-11-Ethyl-28-hydroxy-10-methyl-21,26-diazapentacyclo[23.2.1.0.0.0]octacosa-1(28),3,13,18-tetraene-2,20,27-trione
Ikarugamycin
tu-6239 c3

Biological Activity

[Description]:

Ikarugamycin is an antibiotic and a inhibitor of clathrin-mediated endocytosis (CME)[1].

[Related Catalog]:

Research Areas >> Others

Signaling Pathways >> Others >> Others

[Target]

Clathrin-mediated endocytosis[1]

[In Vitro]

Ikarugamycin has an IC50 of 2.7 μM in H1299 cells[1].

[References]

[1]. Elkin SR, et al. Ikarugamycin: A Natural Product Inhibitor of Clathrin-Mediated Endocytosis. Traffic. 2016 Oct;17(10):1139-49.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
741.9±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₉H₃₈N₂O₄

[ Molecular Weight ]:
478.62

[ Flash Point ]:
402.5±32.9 °C

[ Exact Mass ]:
478.283173

[ PSA ]:
95.50000

[ LogP ]:
5.05

[ Vapour Pressure ]:
0.0±5.6 mmHg at 25°C

[ Index of Refraction ]:
1.604

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NI0625500

CHEMICAL NAME :: Ikarugamycin

CAS REGISTRY NUMBER :: 36531-78-9

LAST UPDATED :: 199206

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C29-H38-N2-O4

MOLECULAR WEIGHT :: 478.69

WISWESSER LINE NOTATION :: T I5 H6 F5-17-5 A CV UVM D&MV DU NU SU C&HTTTT&J AQ L2

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 :: >500 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: 25,271,1972

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6 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: 25,271,1972

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >250 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: 25,271,1972

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

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: 25,271,1972

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301

[ Precautionary Statements ]:
P301 + P310

[ Hazard Codes ]:
T

[ RIDADR ]:
UN 2811 6.1 / PGIII

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Pathogen- and Host-Directed Antileishmanial Effects Mediated by Polyhexanide (PHMB).

PLoS Negl. Trop. Dis. 9 , e0004041, (2015)

Cutaneous leishmaniasis (CL) is a neglected tropical disease caused by protozoan parasites of the genus Leishmania. CL causes enormous suffering in many countries worldwide. There is no licensed vacci...

Clathrin-dependent and independent endocytic pathways in tobacco protoplasts revealed by labelling with charged nanogold.

J. Exp. Bot. 59(11) , 3051-68, (2008)

Positively charged nanogold was used as a probe to trace the internalization of plasma membrane (PM) domains carrying negatively charged residues at an ultrastructural level. The probe revealed distin...

Distinct endocytic pathways identified in tobacco pollen tubes using charged nanogold.

J. Cell Sci. 120(Pt 21) , 3804-19, (2007)

In an attempt to dissect endocytosis in Nicotiana tabacum L. pollen tubes, two different probes--positively or negatively charged nanogold--were employed. The destiny of internalized plasma membrane d...