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Aclarubicin

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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 Molecular Structure of 57576-44-0 (Aclarubicin) Hazard Symbols ToxicT
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

Aclarubicin Synthetic route

16234-96-1

(+)-aklavinone

A

57576-44-0

aclacinomycin A

B

aclacinomycin X

Conditions
ConditionsYield
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;
57576-44-0

aclacinomycin A

16234-96-1

(+)-aklavinone

Conditions
ConditionsYield
With hydrogenchloride In water at 90℃;100%
69489-87-8

D-galactonic acid hydrazide

57576-44-0

aclacinomycin A

C48H65N3O20

Conditions
ConditionsYield
In dimethyl sulfoxide at 20℃; for 1h; Inert atmosphere;35%
57576-44-0

aclacinomycin A

11-deoxy-β-rhodomycin A

Conditions
ConditionsYield
With aclacinomycin-10-hydroxylase from streptomyces purpurascens Reagent/catalyst; Enzymatic reaction;
57576-44-0

aclacinomycin A

C50H71NO16Si2

Conditions
ConditionsYield
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
57576-44-0

aclacinomycin A

C44H53NO17

Conditions
ConditionsYield
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
57576-44-0

aclacinomycin A

7-[2-deoxy-3,4-tetraisopropyldisiloxyl-α-L-fucopyranosyl-(1→4)-3-amino-2,3-dideoxy-α-L-fucopyranoside]-aklavinone

Conditions
ConditionsYield
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
57576-44-0

aclacinomycin A

7-[2-deoxy-α-L-fucopyranosyl-(1→4)-3-amino-2,3-dideoxy-α-L-fucopyranoside]-aklavinone

Conditions
ConditionsYield
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
57576-44-0

aclacinomycin A

C52H61NO18

Conditions
ConditionsYield
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
57576-44-0

aclacinomycin A

3',3'-didesmethyl-aclarubicin

Conditions
ConditionsYield
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

Aclarubicin Specification

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.

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