Carubicin

Names

[ Name ]:
Carubicin

[Synonym ]:
(1S,3S)-3-Acetyl-3,5,10,12-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside
Carminomycin
(1S,3S)-3-Acetyl-3,5,10,12-tetrahydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside
Carminomycin I
Antibiotic R-588A
Carminomicin I
(1S,3S)-3-Acetyl-1,2,3,4,6,11-hexahydro-3,5,10,12-tetrahydroxy-6,11-dioxo-1-naphthacenyl 3-Amino-2,3,6-trideoxy-a-L-lyxo-hexopyranoside
Karminomitsin
5,12-Naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-1,6,8,11-tetrahydroxy-, (8S-cis)-
4-O-Demethyldaunorubicin
5,12-Naphthacenedione, 8-acetyl-10-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-1,6,8,11-tetrahydroxy-, (8S,10S)-
Karminomycin
(8S-cis)-Acetyl-10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-1,6,8,11-tetrahydroxy-5,12-naphthacenedione
Carubicin

Biological Activity

[Description]:

Carubicin (Carminomycin) is a microbially-derived compound. Carubicin is an effective inhibitor of VHL-defective (VHL−/−) CCRCC cell proliferation. Carubicin also induces apoptosis by a mechanism independent of p53 or hypoxia-inducible factor HIF2. Carubicin has the potential for the research of cancer diseases[1][2].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Infection

[References]

[1]. [1]Woldemichael GM, et al. Carminomycin I is an apoptosis inducer that targets the Golgi complex in clear cell renal carcinoma cells. Cancer Res. 2011 Jan 1;71(1):134-42.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
750.6±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₆H₂₇NO₁₀

[ Molecular Weight ]:
513.493

[ Flash Point ]:
407.7±32.9 °C

[ Exact Mass ]:
513.163513

[ PSA ]:
196.84000

[ LogP ]:
3.54

[ Vapour Pressure ]:
0.0±2.6 mmHg at 25°C

[ Index of Refraction ]:
1.727

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QI9293250

CHEMICAL NAME :: 5,12-Naphthacenedione, 8-acetyl-10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hex opyranosyl)oxy)- 7,8,9,10-tetrahydro-1,6,8,11-tetrahydroxy-, (8S-cis)-

CAS REGISTRY NUMBER :: 50935-04-1

LAST UPDATED :: 199406

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C26-H27-N-O10

MOLECULAR WEIGHT :: 513.54

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 :: 7250 ug/kg

TOXIC EFFECTS :: Behavioral - tremor Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1100 ug/kg

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

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3800 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - tremor Nutritional and Gross Metabolic - weight loss or decreased weight gain

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3400 ug/kg

TOXIC EFFECTS :: Behavioral - tremor Gastrointestinal - hypermotility, diarrhea Nutritional and Gross Metabolic - weight loss or decreased weight gain

MUTATION DATA

TYPE OF TEST :: Mutation test systems - not otherwise specified

TEST SYSTEM :: Rodent - mouse Leukocyte

DOSE/DURATION :: 490 nmol/L

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: 34,1596,1981

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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