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Ascomycin

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Name

Ascomycin

EINECS 658-052-0
CAS No. 11011-38-4 Density 1.19 g/cm3
PSA 178.36000 LogP 4.41080
Solubility N/A Melting Point 153-157℃
Formula C43H69NO12 Boiling Point 868.3 °C at 760 mmHg
Molecular Weight 792.02 Flash Point 478.9 °C
Transport Information N/A Appearance White Powder
Safety Risk Codes  Xn:Harmful;
Molecular Structure Molecular Structure of 11011-38-4 (Ascomycin) Hazard Symbols R20/21/22:;
Synonyms

(3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-8-Ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-[(1E)-2-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-methylethenyl]-14,16-dimethoxy-4,10,12,18-tetramethyl-15,19-epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone;Immunomycin;

 

Ascomycin Synthetic route

11011-38-4

ascomycin

18162-48-6

tert-butyldimethylsilyl chloride

C56H99NO12Si2

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 108h;81%
11011-38-4

ascomycin

108-24-7

acetic anhydride

ascomycin 24,33-diacetate

Conditions
ConditionsYield
With dmap In pyridine at 0℃; for 1.5h;
108-05-4

vinyl acetate

11011-38-4

ascomycin

33-acetyl ascomycin

Conditions
ConditionsYield
In toluene at 30℃; for 80h;

Ascomycin Specification

The Ascomycin with CAS registry number of 11011-38-4 is also known as Immunomycin. The systematic name and product name are the same. It belongs to product categories of Immunosuppressant. In addition, the formula is C43H69NO12 and the molecular weight is 792.02. What's more, this chemical should be stored in sealed containers in cool, dry place at -20 °C. This chemical is prepared by the fermentation of Streptomyces hygroscopicus. What's more, it can be used to treat autoimmune diseases and skin diseases, and can help prevent rejection after an organ transplant.

Physical properties about Ascomycin are: (1)ACD/LogP: 3.81; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 3.81; (4)ACD/LogD (pH 7.4): 3.81; (5)ACD/BCF (pH 5.5): 460.15; (6)ACD/BCF (pH 7.4): 458.91; (7)ACD/KOC (pH 5.5): 2803.52; (8)ACD/KOC (pH 7.4): 2795.96; (9)#H bond acceptors: 13; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 9; (12)Index of Refraction: 1.546; (13)Molar Refractivity: 209.73 cm3; (14)Molar Volume: 661.8 cm3; (15)Surface Tension: 51.3 dyne/cm; (16)Density: 1.19 g/cm3; (17)Flash Point: 478.9 °C; (18)Enthalpy of Vaporization: 143.39 kJ/mol; (19)Boiling Point: 868.3 °C at 760 mmHg; (20)Vapour Pressure: 3.45E-35 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CCC1C=C(CC(CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C(CC1=O)O)C)C(=CC4CCC(C(C4)OC)O)C)O)C)OC)OC)C)C
2. Isomeric SMILES: CC[C@@H]1/C=C(/C[C@@H](C[C@@H]([C@@H]2[C@H](C[C@H]([C@@](O2)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@@H]([C@@H]([C@H](CC1=O)O)C)/C(=C/[C@H]4CC[C@@H]([C@@H](C4)OC)O)/C)O)C)OC)OC)C)\C
3. InChI: InChI=1S/C43H69NO12/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)44-16-12-11-13-31(44)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-32(45)35(22-29)52-7/h18,20,25,27-33,35-39,45-46,51H,10-17,19,21-23H2,1-9H3/b24-18+,26-20+/t25-,27+,28+,29+,30+,31-,32-,33-,35+,36-,37-,38+,39+,43+/m0/s1
4. InChIKey: ZDQSOHOQTUFQEM-BFFCMSJVSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD intraperitoneal > 100mg/kg (100mg/kg)   Journal of Antibiotics, Series A. Vol. 15, Pg. 231, 1962.

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