Record Information
Version1.0
Creation Date2010-05-13 19:36:34 UTC
Update Date2026-04-06 13:19:37 UTC
Accession NumberCHEM002722
Identification
Common NameEmestrin
ClassSmall Molecule
DescriptionEmestrin is a mycotoxin produced by fungi of the genus Emericella. It mainly targets the heart, liver and thymus. 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. (1, 2)
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Ester
  • Ether
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
SynonymsNot Available
Chemical FormulaC27H22N2O10S2
Average Molecular Mass598.601 g/mol
Monoisotopic Mass598.072 g/mol
CAS Registry Number97816-62-1
IUPAC Name20,24,32-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
Traditional Name20,24,32-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
SMILESCOC1=CC=CC2=C1OC1=C(O)C=CC(=C1)C(O)C13SSC4(C(O)C5=COC=CC(OC2=O)C5N4C1=O)C(=O)N3C
InChI IdentifierInChI=1S/C27H22N2O10S2/c1-28-24(34)27-22(32)14-11-37-9-8-16-19(14)29(27)25(35)26(28,40-41-27)21(31)12-6-7-15(30)18(10-12)38-20-13(23(33)39-16)4-3-5-17(20)36-2/h3-11,16,19,21-22,30-32H,1-2H3
InChI KeyVASYTSFNISZKEL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolactams
Sub ClassNot Available
Direct ParentMacrolactams
Alternative Parents
Substituents
  • Macrolactam
  • Diaryl ether
  • Alpha-amino acid or derivatives
  • Epipolythiodioxopiperazine
  • Thiodioxopiperazine
  • Anisole
  • Dioxopiperazine
  • 2,5-dioxopiperazine
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • N-methylpiperazine
  • N-alkylpiperazine
  • 1,4-diazinane
  • Dithiazinane
  • Piperazine
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Secondary alcohol
  • Carboxamide group
  • Carboxylic acid ester
  • Lactam
  • Lactone
  • Organic disulfide
  • Oxacycle
  • Polyol
  • Monocarboxylic acid or derivatives
  • Ether
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Azacycle
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Carbonyl group
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.22 g/LALOGPS
logP2.13ALOGPS
logP1.94ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.35ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area155.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity145.62 m³·mol⁻¹ChemAxon
Polarizability55.86 ųChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0300390000-d6bac3f57cfb576fa9c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00m1-0300190000-b0b2a7ef53e70f963559Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0080-5900000000-e7b9da91e4433e9d7154Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000390000-eb4f747f9ea2882fd3d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0059030000-effe98be2fce767b622eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9521120000-5c52de580c6d92117e6aSpectrum
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (4)
Mechanism of ToxicityEmestrin 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. (1, 3)
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseLD50: 13.0 mg/kg (Intraperitoneal, Mouse) (2)
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesEmestrin 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.
Minimum Risk LevelNot Available
Health EffectsEmestrin causes damage to the heart, liver and thymus. It can lead to cardiac failure. (2)
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID78169525
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available