CID 73555
Basic information
- CAS
97816-62-1- Standard SMILES
COc1cccc2c1Oc1cc(ccc1O)[C@H](O)[C@@]13SS[C@@]4(C(=O)N1C)[C@H](O)C1=COC=C[C@H](OC2=O)[C@@H]1N4C3=O- InChIKey
VASYTSFNISZKEL-DCTKBWBHSA-N- Molecular formula
- C27H22N2O10S2
- Average molar mass
- 598.6 g/mol
- Monoisotopic mass
- 598.07158725
Overview
(1R,3R,9S,24S,25S,32R)-20,24,32-Trihydroxy-16-methoxy-29-methyl-6,10,18-trioxa-26,27-dithia-2,29-diazaheptacyclo[23.2.2.11,4.12,25.119,23.03,9.012,17]dotriaconta-4,7,12(17),13,15,19,21,23(31)-octaene-11,28,30-trione has been reported in Aspergillus striatus with data available.
Names & identifiers
- Preferred name
- CID 73555
- IUPAC
- (1R,3R,9S,24S,25S,32R)-20,24,32-trihydroxy-16-methoxy-29-methyl-6,10,18-trioxa-26,27-dithia-2,29-diazaheptacyclo[23.2.2.11,4.12,25.119,23.03,9.012,17]dotriaconta-4,7,12(17),13,15,19,21,23(31)-octaene-11,28,30-trione
- English name
- emestrin
- Molecular formula
- C27H22N2O10S2
- Molecular weight
- 598.6
Names & synonyms
(1R,3R,9S,24S,25S,32R)-20,24,32-Trihydroxy-16-methoxy-29-methyl-6,10,18-trioxa-26,27-dithia-2,29-diazaheptacyclo[23.2.2.11,4.12,25.119,23.03,9.012,17]dotriaconta-4,7,12(17),13,15,19,21,23(31)-octaene-11,28,30-trioneemestrin AemestrinEmestrine(1R,2R,6aS,20S,21R,22bS)-6a,22b-dihydro-2,16,20-trihydroxy-12-methoxy-25-methyl-2H,8H,20H,22H-1,21-epidithio-21,1-(iminomethano)-9,13:15,19-dimetheno-4,7,14-trioxa-22a-azacyclononadec[cd]azulene-8,22,26-trione2H,8H,20H,22H-1,21-Epidithio-21,1-(iminomethano)-9,13:15,19-dimetheno-4,7,14-trioxa-22a-azacyclononadec[cd]azulene-8,22,26-trione, 6a,22b-dihydro-2,16,20-trihydroxy-12-methoxy-25-methyl-, (1R,2R,6aS,20S,21R,22bS)-
Database identifiers
- CAS
97816-62-1- PubChem CID
- 73555
- DTXSID
DTXSID901046701
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 206 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 1
- Heavy atoms
- 41
- Formal charge
- 0
- Complexity
- 1,220
Physicochemical properties
- Boiling point
- 1041.7 · 1041.7±65.0 °C(Predicted)
- Density
- 1.78 · 1.78±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble
- form
- A solid
- pka
- 8.88 · 8.88±0.60(Predicted)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Health EffectsEmestrin causes damage to the heart, liver and thymus. It can lead to cardiac failure. (A3041)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary
Emestrin causes degeneration of the mitochondria in both cardiac muscle cells and hepatocytes, leading to necrosis. It is also known to act as an antagonist at the chemokine receptor, reducing the inflammatory effects of autoimmune disorders including rheumatoid arthritis, multiple sclerosis, atherosclerosis. Emestrin may also cause DNA fragmentation. (A3040, A3042)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Chemistry & industry
Uses & manufacturing
Uses
Emestrin is a mycotoxin produced by fungi of the genus Emericella. Its action at the chemokine receptor has lead to its consideration as a possible treatment for autoimmune disorders including rheumatoid arthritis, atherosclerosis, multiple sclerosis, and infectious diseases.
Applications
DescriptionEmestrin is a mycotoxin originally isolated from E. striata that has antimicrobial, immunomodulatory, and cytotoxic activities.1,2,3,4,5 It is active against the fungi C. albicans and C. neoformans, as well as the bacteria E. coli, S. aureus, and methicillin-resistant S. aureus (MRSA; IC50s = 3.94, 0.6, 2.21, 4.55, and 2.21 μg/ml, respectively).2 Emestrin is a chemokine (C-C motif) receptor 2 (CCR2) antagonist (IC50 = 5.4 μM in a radioligand binding assay using isolated human monocytes).3 Emestrin (0.1 μg/ml) induces apoptosis in HL-60 cells.4 It induces heart, thymus, and liver tissue necrosis in mice when administered at doses ranging from 18 to 30 mg/kg.5
UsesEmestrin is a mycotoxin originally isolated from E. striata that has antimicrobial, immunomodulatory, and cytotoxic activities. It is active against the fungi C. albicans and C. neoformans, as well as the bacteria E. coli, S. aureus, and methicillin-resistant S. aureus (MRSA; IC50s=3.94, 0.6, 2.21, 4.55, and 2.21 μg/mL, respectively).2 Emestrin is a chemokine (C-C motif) receptor 2 (CCR2) antagonist (IC50=5.4 μM in a radioligand binding assay using isolated human monocytes).3 Emestrin (0.1 μg/mL) induces apoptosis in HL-60 cells. It induces heart, thymus, and liver tissue necrosis in mice when administered at doses ranging from 18 to 30 mg/kg.
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