concanamycin A

Names

[ Name ]:
concanamycin A

[Synonym ]:
antibioticx4357b
S-45A
MFCD00210037
Antibiotic A661I
(5R)-3-O-(4-O-Carbamoyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2,4-dideoxy-1-C-{(2S,3R,4S)-4-[(2R,3S,4E,6E,9R,10S,11S,12R,13R,14E,16Z)-11-ethyl-10,12-dihydroxy-3,17-dimethoxy-7,9,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6,14,16-tetraen-2-yl]-3-hydroxypentan-2-yl}-4-methyl-5-[(1E)-prop-1-en-1-yl]-α-D-threo-pentopyranose
FOLIMYCIN,STREPTOMYCES SP
α-D-threo-Pentopyranose, 3-O-[4-O-(aminocarbonyl)-2,6-dideoxy-β-D-arabino-hexopyranosyl]-2,4-dideoxy-1-C-[(1S,2R,3S)-3-[(2R,3S,4E,6E,9R,10S,11S,12R,13R,14E,16Z)-11-ethyl-10,12-dihydroxy-3,17-dimethoxy-7,9,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6,14,16-tetraen-2-yl]-2-hydroxy-1-methylbutyl]-4-methyl-5-C-[(1E)-1-propen-1-yl]-, (5R)-
A661-I
FOLIMYCIN
Antibiotic S-45A
x4357b
α-D-threo-Pentopyranose, 3-O-[4-O-(aminocarbonyl)-2,6-dideoxy-β-D-arabino-hexopyranosyl]-2,4-dideoxy-1-C-[(1S,2R,3S)-3-[(2R,3S,4E,6E,9R,10S,11S,12R,13R,14E,16Z)-11-ethyl-10,12-dihydroxy-3,17-di methoxy-7,9,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6,14,16-tetraen-2-yl]-2-hydroxy-1-methylbutyl]-4-methyl-5-C-[(1E)-1-propen-1-yl]-, (5R)-
Concanamycin A,(3Z,5E,7R,8R,9S,10S,11R,13E,15E,17S,18R)-18-[(1S,2R,3S)-3-[(2R,4R,5S,6R)-4-[[4-O-(Aminocarbonyl)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy]tetrahydro-2-hydroxy-5-methyl-6-(1E)-1-propenyl-2H-pyran-2-yl]-2-hydroxy-1-methylbutyl]-9-ethyl-8,10-
CONCANAMYCIN A
(5R)-3-O-(4-O-Carbamoyl-2,6-dideoxy-β-D-arabino-hexopyranosyl)-2,4-dideoxy-1-C-{(2S,3R,4S)-4-[(2R,3S,4E,6E,9R,10S,11S,12R,13R,14E,16Z)-11-ethyl-10,12-dihydroxy-3,17-dimethoxy-7,9,13,15-tetramethyl- 18-oxooxacyclooctadeca-4,6,14,16-tetraen-2-yl]-3-hydroxy-2-pentanyl}-4-methyl-5-[(1E)-1-propen-1-yl]-α-D-threo-pentopyranose

Biological Activity

[Description]:

Concanamycin A (Antibiotic X 4357B; Concanamycin; X 4357B) is a macrolide antibiotic and a specific vacuolar type H+-ATPase (V-ATPase) inhibitor[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Membrane Transporter/Ion Channel >> Proton Pump

[Target]

Vacuolar type H+-ATPase[1]

[References]

[1]. Togashi K, et al. Concanamycin A, a vacuolar type H(+)-ATPase inhibitor, induces cell death in activated CD8(+) CTL. Cytotechnology. 1997 Nov;25(1-3):127-35.

[2]. Eswarappa SM, et al. Folimycin (concanamycin A) inhibits LPS-induced nitric oxide production and reduces surface localization of TLR4 in murine macrophages. Innate Immun. 2008 Feb;14(1):13-24.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
966.4±65.0 °C at 760 mmHg

[ Melting Point ]:
179-180℃ (dichloromethane ethanol )

[ Molecular Formula ]:
C₄₆H₇₅NO₁₄

[ Molecular Weight ]:
866.09

[ Flash Point ]:
538.3±34.3 °C

[ Exact Mass ]:
865.518738

[ PSA ]:
225.92000

[ LogP ]:
3.88

[ Vapour Pressure ]:
0.0±0.6 mmHg at 25°C

[ Index of Refraction ]:
1.555

[ Storage condition ]:
−20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CB9732000

CHEMICAL NAME :: Antibiotic X 4357 B

CAS REGISTRY NUMBER :: 80890-47-7

LAST UPDATED :: 199712

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C46-H75-N-O14

MOLECULAR WEIGHT :: 866.22

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 :: 21 mg/kg

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

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4076802

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2450 ug/kg

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

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4076802

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300 + H310 + H330-H319

[ Precautionary Statements ]:
P260-P264-P280-P284-P301 + P310-P302 + P350

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T+

[ Risk Phrases ]:
26/27/28-36

[ Safety Phrases ]:
26-36/37/39-45

[ RIDADR ]:
UN 3462 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
CB9732000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

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