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Ascomycin

Ascomycin structure

CAS No:
11011-38-4
Formula:
C43H69NO12
Chemical Name:
Ascomycin
Synonyms:
ASCOMYCIN, STREPTOMYCES HYGROSCOPICUS;ASCOMYCIN, STREPTOMYCES HYGROSCOPICUS VAR ASCOMYCETICUS;FR-900520;FK-520;IMMUNOMYCIN;AAG;ASCOMYCIN (IMMUNOMYCIN, FR-900520) \ INH IBITS CALCINEURIN (PP2B);(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
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Ascomycin (11011-38-4) is an analog of FK-506 (Cat.# 10-1103). Potent immunosuppressant1. Binds to FKBP122 and inhibits calcineurin and NFAT. Ascomycin displays anti-inflammatory effects in skin diseases3. Cell permeable and active in vivo.

White powder, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from biological fermentation.

An ethyl analog of FK506 with similar immunosuppressant properties. Acts by binding to immunophilins. Inhibits the synthesis of Th-1 and Th-2 type cytokines in target cells.

Ascomycin Basic Attributes

Molecular Weight：

792.01

Exact Mass：

792.01

EC Number：

658-052-0

Color/Form：

White

Characteristics

PSA：

178.36000

XLogP3：

3.81

Density：

1.2±0.1 g/cm3

Melting Point：

158 - 161°C

Boiling Point：

868.3±75.0 °C at 760 mmHg

Flash Point：

478.9±37.1 °C

Refractive Index：

1.546

Storage Conditions：

-20°C

Critical Temperature & Pressure：

-20°C

Safety Information

wgk germany：

WGK 2

safety instructions：

S36/37

RTECS Number：

CI7570000

Marks：

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P264, P270, P273, P281, P301+P312, P308+P313, P330, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Ascomycin Use and Manufacturing

This antifungal antibiotic (FW = 792.02 g/mol; CAS 104987-12-4; Solubility: 50 mM in DMSO), also known as FK520, isolated from Streptomyces hygroscopicus, is also a powerful immunosuppressant. Note that ascomycin is a structural analogue of tacrolimus (or FK506) and, as such, operates by a similar mechanism of action (See Tacrolimus). Ascomycin inhibits allogenic T-lymphocyte proliferation and calcineurin phosphatase activity.

A potent immunosuppressive agent and could be used as a potential therapeutic agent for autoimmune diseases.

Computed Properties

Molecular Weight:792.0
XLogP3:2.5
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:12
Rotatable Bond Count:6
Exact Mass:791.48197664
Monoisotopic Mass:791.48197664
Topological Polar Surface Area:178
Heavy Atom Count:56
Complexity:1430
Undefined Atom Stereocenter Count:14
Undefined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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