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Name |
Aclarubicin |
EINECS | 260-824-3 |
CAS No. | 57576-44-0 | Density | 1.42 g/cm3 |
PSA | 217.05000 | LogP | 3.15770 |
Solubility | Soluble in chloroform or ethyl acetate, insoluble in n-hexane, ether or petroleum ether | Melting Point |
151-153 °C |
Formula | C42H53NO15 | Boiling Point | 897.676 °C at 760 mmHg |
Molecular Weight | 811.881 | Flash Point | 496.696 °C |
Transport Information | UN 3249 | Appearance | N/A |
Safety | 36/37/39-45 | Risk Codes | 25 |
Molecular Structure | Hazard Symbols | T | |
Synonyms |
1-Naphthacenecarboxylicacid,2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-[[2,3,6-trideoxy-4-O-[2,6-dideoxy-4-O-[(2R-trans)-tetrahydro-6-methyl-5-oxo-2H-pyran-2-yl]-a-L-lyxo-hexopyranosyl]-3-(dimethylamino)-a-L-lyxo-hexopyranosyl]oxy]-,methyl ester, [1R-(1a,2b,4b)]-;Aclacinomycin A;Aclacur;Aclarubicin;Antibiotic3082A;Antibiotic 77-3082A;Antibiotic MA 144A1;Jaclacin;NSC 208734; |
Article Data | 1 |
Conditions | Yield |
---|---|
With soybean meal; dipotassium hydrogenphosphate; D-glucose; KE303 of S. galilaeus MA144-M1; magnesium sulfate; copper(II) sulfate; iron(II) sulfate; zinc(II) sulfate; sodium chloride; manganese(ll) chloride; starch; yeast extract In water at 28℃; for 96h; |
aclacinomycin A
(+)-aklavinone
Conditions | Yield |
---|---|
With hydrogenchloride In water at 90℃; | 100% |
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere; | 35% |
aclacinomycin A
Conditions | Yield |
---|---|
With aclacinomycin-10-hydroxylase from streptomyces purpurascens Reagent/catalyst; Enzymatic reaction; |
aclacinomycin A
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 90 °C 2: (triphenylphosphine)gold(I) chloride; silver(I) triflimide / dichloromethane / -20 °C / Molecular sieve View Scheme |
aclacinomycin A
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride / water / 90 °C 2: (triphenylphosphine)gold(I) chloride; silver(I) triflimide / dichloromethane / 0.5 h / -20 °C / Molecular sieve 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; aq. phosphate buffer / 1.5 h / 0 °C / pH 7 View Scheme |
aclacinomycin A
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride / water / 90 °C 2: (triphenylphosphine)gold(I) chloride; silver(I) triflimide / dichloromethane / -20 °C / Molecular sieve 3: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 0.5 h View Scheme |
aclacinomycin A
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: hydrogenchloride / water / 90 °C 2: (triphenylphosphine)gold(I) chloride; silver(I) triflimide / dichloromethane / -20 °C / Molecular sieve 3: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 0.5 h 4: pyridine; pyridine hydrofluoride / 0 °C View Scheme |
aclacinomycin A
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 90 °C 2: (triphenylphosphine)gold(I) chloride; silver(I) triflimide / dichloromethane / 0.5 h / -20 °C / Molecular sieve View Scheme |
aclacinomycin A
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: hydrogenchloride / water / 90 °C 2: (triphenylphosphine)gold(I) chloride; silver(I) triflimide / dichloromethane / 0.5 h / -20 °C / Molecular sieve 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; aq. phosphate buffer / 1.5 h / 0 °C / pH 7 4: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) / dichloromethane / 0.25 h / Inert atmosphere View Scheme |
The Aclarubicin, with the CAS registry number 57576-44-0, is also known as Aclacinomycin A. It belongs to the product categories of Interferes with DNA Synthesis; Antibiotics; Antibiotics A to; Antibiotics A-F Antibiotics; Antibiotics by Application; Antineoplastic and Immunosuppressive Antibiotics Antibiotics; Mechanism of Action; Antitumour. Its EINECS number is 260-824-3. This chemical's molecular formula is C42H53NO15 and molecular weight is 811.87. What's more, its systematic name is Methyl (1R,2R,4S)-2-ethyl-1,2,3,4,6,11-hexahydro-2,5,7-trihydroxy-6,11-dioxo-4-((2,3,6-trideoxy-4-O-(2,6-dideoxy-4-O-((2R,6S)-tetrahydro-6-methyl-5-oxo-2H-pyran-2-yl)-alpha-L-lyxo-hexopyranosyl)-3-(dimethylamino)-alpha-L-lyxo-hexopyranosyl)oxy)-1-naphthacenecarboxylate. This chemical is the second generation anti-tumor antibiotic and cell cycle nonspecific. It can restrain DNA and RNA protein. And it, as Anti-tumor antibiotic, is mainly used for lung, breast, gastrointestinal cancer, acute leukemia.
Physical properties of Aclarubicin are: (1)ACD/LogP: 3.987; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 1.63; (4)ACD/LogD (pH 7.4): 1.75; (5)ACD/BCF (pH 5.5): 2.78; (6)ACD/BCF (pH 7.4): 3.65; (7)ACD/KOC (pH 5.5): 15.50; (8)ACD/KOC (pH 7.4): 20.35; (9)#H bond acceptors: 16; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 14; (12)Polar Surface Area: 217.05 Å2; (13)Index of Refraction: 1.629; (14)Molar Refractivity: 202.551 cm3; (15)Molar Volume: 569.852 cm3; (16)Polarizability: 80.298×10-24cm3; (17)Surface Tension: 70.4 dyne/cm; (18)Density: 1.425 g/cm3; (19)Flash Point: 496.696 °C; (20)Enthalpy of Vaporization: 136.704 kJ/mol; (21)Boiling Point: 897.676 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
When you are using this chemical, please be cautious about it as the following:
This chemical is toxic if swallowed. When using it, you need wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES: O=C2c1cc7c(c(O)c1C(=O)c3c2cccc3O)[C@@H](O[C@@H]6O[C@H]([C@@H](O[C@@H]5O[C@H]([C@@H](O[C@@H]4O[C@H](C(=O)CC4)C)[C@@H](O)C5)C)[C@@H](N(C)C)C6)C)C[C@](O)(CC)[C@@H]7C(=O)OC
(2)Std. InChI: InChI=1S/C42H53NO15/c1-8-42(51)17-28(33-22(35(42)41(50)52-7)14-23-34(38(33)49)37(48)32-21(36(23)47)10-9-11-26(32)45)56-30-15-24(43(5)6)39(19(3)54-30)58-31-16-27(46)40(20(4)55-31)57-29-13-12-25(44)18(2)53-29/h9-11,14,18-20,24,27-31,35,39-40,45-46,49,51H,8,12-13,15-17H2,1-7H3/t18-,19-,20-,24-,27-,28-,29-,30-,31-,35-,39+,40+,42+/m0/s1
(3)Std. InChIKey: USZYSDMBJDPRIF-SVEJIMAYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LDLo | intravenous | 5mg/kg (5mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: FOOD INTAKE (ANIMAL) | Japanese Journal of Antibiotics. Vol. 33, Pg. 138, 1980. |
mammal (species unspecified) | LD50 | intraperitoneal | 25mg/kg (25mg/kg) | Antibiotiki. Vol. 29, Pg. 748, 1984. | |
mouse | LD50 | intraperitoneal | 16100ug/kg (16.1mg/kg) | Antibiotiki i Meditsinskaya Biotekhnologiya. Antibiotics and Medical Biotechnology. Vol. 30, Pg. 918, 1985. | |
mouse | LD50 | intravenous | 16500ug/kg (16.5mg/kg) | Antibiotiki i Meditsinskaya Biotekhnologiya. Antibiotics and Medical Biotechnology. Vol. 30, Pg. 918, 1985. | |
mouse | LD50 | oral | 30100ug/kg (30.1mg/kg) | Antibiotiki i Meditsinskaya Biotekhnologiya. Antibiotics and Medical Biotechnology. Vol. 30, Pg. 918, 1985. | |
mouse | LD50 | subcutaneous | 22100ug/kg (22.1mg/kg) | Antibiotiki i Meditsinskaya Biotekhnologiya. Antibiotics and Medical Biotechnology. Vol. 30, Pg. 918, 1985. | |
rat | LD50 | intraperitoneal | 17400ug/kg (17.4mg/kg) | BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED) BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE | Antibiotiki i Meditsinskaya Biotekhnologiya. Antibiotics and Medical Biotechnology. Vol. 32, Pg. 915, 1987. |
rat | LD50 | intravenous | 25710ug/kg (25.71mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: FOOD INTAKE (ANIMAL) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Japanese Journal of Antibiotics. Vol. 33, Pg. 138, 1980. |
rat | LD50 | oral | 58560ug/kg (58.56mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: FOOD INTAKE (ANIMAL) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Japanese Journal of Antibiotics. Vol. 33, Pg. 138, 1980. |
rat | LD50 | subcutaneous | 20mg/kg (20mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" BEHAVIORAL: FOOD INTAKE (ANIMAL) | Japanese Journal of Antibiotics. Vol. 33, Pg. 138, 1980. |