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Record Information
Version2.0
Creation Date2010-05-13 19:36:34 UTC
Update Date2014-12-24 20:26:29 UTC
Accession NumberT3D3754
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)
Compound Type
  • Amide
  • Amine
  • Ester
  • Ether
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(1R,3S,9S,23S,24R,34R)-19,23,34-Trihydroxy-15-methoxy-30-methyl-6,10,17-trioxa-25,26,27,28-tetrathia-2,30-diazaheptacyclo[22.4.2.11,4.12,24.112,16.118,22.03,9]tetratriaconta-4,7,12(33),13,15 ,18(32),19,21-octaene-11,29,31-trione
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 KeyInChIKey=VASYTSFNISZKEL-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
LogPNot 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0300390000-d6bac3f57cfb576fa9c1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00m1-0300190000-b0b2a7ef53e70f963559JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0080-5900000000-e7b9da91e4433e9d7154JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000390000-eb4f747f9ea2882fd3d9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0059030000-effe98be2fce767b622eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9521120000-5c52de580c6d92117e6aJSpectraViewer
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID73555
ChEMBL IDNot Available
ChemSpider IDNot Available
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
  1. Herath KB, Jayasuriya H, Ondeyka JG, Polishook JD, Bills GF, Dombrowski AW, Cabello A, Vicario PP, Zweerink H, Guan Z, Singh SB: Isolation and structures of novel fungal metabolites as chemokine receptor (CCR2) antagonists. J Antibiot (Tokyo). 2005 Nov;58(11):686-94. [16466022 ]
  2. Terao K, Ito E, Kawai K, Nozawa K, Udagawa S: Experimental acute poisoning in mice induced by emestrin, a new mycotoxin isolated from Emericella species. Mycopathologia. 1990 Nov;112(2):71-9. [2293035 ]
  3. Ueno Y, Umemori K, Niimi E, Tanuma S, Nagata S, Sugamata M, Ihara T, Sekijima M, Kawai K, Ueno I, et al.: Induction of apoptosis by T-2 toxin and other natural toxins in HL-60 human promyelotic leukemia cells. Nat Toxins. 1995;3(3):129-37. [7648021 ]
  4. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Protein homodimerization activity
Specific Function:
Receptor for the CCL2, CCL7 and CCL13 chemokines. Transduces a signal by increasing intracellular calcium ion levels. Alternative coreceptor with CD4 for HIV-1 infection.
Gene Name:
CCR2
Uniprot ID:
P41597
Molecular Weight:
41914.265 Da
References
  1. Herath KB, Jayasuriya H, Ondeyka JG, Polishook JD, Bills GF, Dombrowski AW, Cabello A, Vicario PP, Zweerink H, Guan Z, Singh SB: Isolation and structures of novel fungal metabolites as chemokine receptor (CCR2) antagonists. J Antibiot (Tokyo). 2005 Nov;58(11):686-94. [16466022 ]
2. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Ueno Y, Umemori K, Niimi E, Tanuma S, Nagata S, Sugamata M, Ihara T, Sekijima M, Kawai K, Ueno I, et al.: Induction of apoptosis by T-2 toxin and other natural toxins in HL-60 human promyelotic leukemia cells. Nat Toxins. 1995;3(3):129-37. [7648021 ]