Ascomycin
Basic information
- CAS
104987-12-4- Standard SMILES
CC[C@@H]1/C=C(\C)C[C@H](C)C[C@H](OC)[C@H]2O[C@@](O)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@H](/C(C)=C/[C@@H]3CC[C@@H](O)[C@H](OC)C3)[C@H](C)[C@@H](O)CC1=O)[C@H](C)C[C@@H]2OC- InChIKey
ZDQSOHOQTUFQEM-NURRSENYSA-N- Molecular formula
- C43H69NO12
- Average molar mass
- 792 g/mol
- Monoisotopic mass
- 791.48197664
Overview
Ascomycin is a macrolide that is produced by the fermentation of Streptomyces hygroscopicus and exhibits strong immunosuppressant properties. It has a role as an immunosuppressive agent, an antifungal agent and a bacterial metabolite. It is a macrolide, an ether, a secondary alcohol and a lactol.
Names & identifiers
- Preferred name
- Ascomycin
- IUPAC
- (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone
- English name
- Ascomycin
- Molecular formula
- C43H69NO12
- Molecular weight
- 792.01
Names & synonyms
ascomycinImmunomycin104987-12-4ChangchuanmycinFK520AUF4U5NSJKL-683590FK-520NSC-106410CHEBI:29582DTXSID80894126FR-520
Show more names
AAGFR-900520AscoMycin solutionTacrolimus USP Related Compound ACBR02FR 520C058028CS-1818
(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone15,19-Epoxy-3H-pyrido(2,1-c)(1,4)oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 8-ethyl-5,6,8,11,12,13,14,15,16,17,18,19,24,25,26,26a-hexadecahydro-5,19-dihydroxy-3-(2-(4-hydroxy-3-methoxycyclohexyl)-1-methylethenyl)-14,16-dimethoxy-4,10,12,18-tetram(1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-((E)-1-((1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl)prop-1-en-2-yl)-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo(22.3.1.04,9)octacos-18-ene-2,3,10,16-tetroneRefChem:916297DTXCID201324166((4Z,6R,7R,8S,10E,12E,14E,16R)-6-hydroxy-16-methoxy-5,7-dimethyl-18,22,24-trioxo-19-azabicyclo(18.3.1)tetracosa-1(23),4,10,12,14,20-hexaen-8-yl) (2R)-2-(cyclohexanecarbonylamino)propanoate435-850-5FK 520
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 178 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 6
- Heavy atoms
- 56
- Formal charge
- 0
- Complexity
- 1,430
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
Physicochemical properties
- Melting point
- 153 · 153-157°C
- Boiling point
- 868 ℃ · 868℃
- Density
- 1.19 · 1.19±0.1 g/cm3(Predicted)
- Flash point
- 110 ° · >110°(230°F)
- storage temp.
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- solubility
- 38.9 mg/mL · ≥38.9 mg/mL in DMSO; insoluble in H2O; ≥98.6 mg/mL in EtOH
- form
- Powder
- pka
- 9.97 · 9.97±0.70(Predicted)
- color
- White to off-white
- Water Solubility
- 65 mg/ml; · Soluble in DMSO at 65mg/ml; soluble in ethanol at 50mg/m; with warming. Very poorly soluble in water
- InChIKey
- ZDQSOHOQTUFQEM-AMASXYNMSA-N
- FDA UNII
- 4 U5NSJK · AUF4U5NSJK
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Hazard information
Regulatory Information
REACH registered substance: ASCOMYCIN (EC: 435-850-5)
15,19-Epoxy-3H-pyrido[2,1-c][1,4]oxaazacyclotricosine-1,7,20,21(4H,23H)-tetrone, 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-, (3S,4R,5S,8R,9E,12S,14S,15R,16S,18R,19R,26aS)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute Tox. 4 (100%)
STOT RE 2 (100%)
Safety data
- F
- 10
- wgk
- 3
- rtecs
- KD4185000
- ridadr
- UN 1648 3 / PGII
- hs_code
- 29419090
- risk_code
- 20/21/22-36-11
- Signal word
- Danger
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.
Substances that inhibit the growth or reproduction of BACTERIA.
Applications
UsesA potent immunosuppressive agent and could be used as a potential therapeutic agent for autoimmune diseases
UsesEverolimus is a semi-synthetic macrocyclic lactone prepared from rapamycin by selective alkylation of the 42-hydroxy group with a silyl-protected hydroxyethyl triflate moiety, followed by addition of an ethylhydroxy moiety to provide greater stability and bioavailability. Like all tacrolimus analogues, everolimus binds to receptor protein, FKBP12. The complex then binds to mTOR preventing it from interacting with target proteins. Everolimus is extensively cited in the literature with over 2,000 citations.
UsesAscomycin is a macrocyclic lactone closely related to tacrolimus and rapamycin. Ascomycin is isolated from several species of Streptomyces and was first reported in 1988. Ascomycin exhibits limited, potent antifungal activity but has found considerable utility as an immunosuppressant.
Additional notes
DefinitionChEBI: A macrolide that is produced by the fermentation of Streptomyces hygroscopicus and exhibits strong immunosuppressant properties.
Related reactions
2 records
Compound notes
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