Please note that T3DB is currently undergoing changes to improve data quality and
website features. You can access the original version of T3DB
here.
T3D3746 - Territrem A
| Record Information | |
|---|---|
| Version | 1.0 |
| Creation Date | 2010-05-10 16:23:41 UTC |
| Update Date | 2013-04-25 08:48:51 UTC |
| Accession Number | T3D3746 |
| Identification | |
| Common Name | Territrem A |
| Description | Territrem A is a tremorgenic mycotoxin found in the fungus Aspergillus terreus, which has been know to contaminate rice crops. Tremorgenic mycotoxins affect central nervous system activity, with their defining characteristic being the tremors that they cause. Territrems induce this effect by inhibiting the enzyme acetylcholinesterase in peripheral nerve endings. (W886, W887) |
| Compound Type |
|
| Chemical Structure |
|
| Synonyms |
|
| Chemical Formula | C28H30O9 |
| Average Molecular Weight | 510.5324 |
| Monoisotopic Molecular Weight | 510.188982558 |
| Chemical IUPAC Name | 7a,11b-dihydroxy-3-(7-methoxy-2H-1,3-benzodioxol-5-yl)-5a,8,8,11a-tetramethyl-7,12-dihydro-6H-2,5-dioxatetraphene-1,11-dione |
| CAS Registry Number | 70407-19-1 |
| SMILES | COC1=CC(=CC2=C1OCO2)C1=CC2=C(CC3(O)C(C)(CCC4(O)C(C)(C)C=CC(=O)C34C)O2)C(=O)O1 |
| InChI Identifier | InChI=1S/C28H30O9/c1-24(2)7-6-21(29)26(4)27(24,31)9-8-25(3)28(26,32)13-16-18(37-25)12-17(36-23(16)30)15-10-19(33-5)22-20(11-15)34-14-35-22/h6-7,10-12,31-32H,8-9,13-14H2,1-5H3 |
| InChI Key | InChIKey=LCJHAHVVYAVVPA-UHFFFAOYSA-N |
| Chemical Taxonomy | |
| Kingdom | Organic Compounds |
| Super Class | Heterocyclic Compounds |
| Class | Naphthopyrans |
| Sub Class | Not Available |
| Direct Parent | Naphthopyrans |
| Alternative Parents |
|
| Molecular Framework | Aromatic Heteropolycyclic Compounds |
| Substituents |
|
| External Descriptors | Not Available |
| External Links | |
| DrugBank ID | Not Available |
| PubChem Compound ID | 115079  |
| KEGG ID | Not Available |
| UniProt ID | Not Available |
| OMIM ID | Not Available |
| ChEBI ID | Not Available |
| BioCyc ID | Not Available |
| CTD ID | Not Available |
| Stitch ID | Not Available |
| PDB ID | Not Available |
| ACToR ID | Not Available |
| Wikipedia Link | Not Available |
| Physical Properties | |
| Appearance | Not Available |
| Melting Point | Not Available |
| Solubility | Not Available |
| Predicted LogP | 2.4436512230000003 |
| Toxicity Profile | |
| Route of Exposure | Oral, dermal, inhalation, and parenteral (contaminated drugs). (W967) |
| Mechanism of Action | Territrems act at the peripheral nerve endings as irreversible inhibitors of acetylcholinesterase. As acetylcholinesterase is needed to hydrolyze the neurotransmitter acetylcholine in cholinergic synapses, inhibition of this enzyme continually potentiates the acetylcholine-induced current of the neuron. It is thought that territrems inhibits acetylcholinesterase by becoming noncovalently trapped within the unique active-site gorge structure of the enzyme. (W886, W887) |
| Metabolism | The biotransformation of territrems involves hydroxylation and 0-demethylation. Metabolism is performed by cytochrome P-450 monooxygenases in the liver, with CYP3A4 and CYP3A5 being the major enzymes used. (W886, W888) |
| Toxicity Values | Not Available |
| Lethal Dose | Not Available |
| Carcinogenicity (IARC Classification) | Not Available |
| Uses/Sources | Territrem A is a tremorgenic mycotoxin found in the fungus Aspergillus terreus. (W886) |
| Minimum Risk Level | Not Available |
| Health Effects | Tremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of cattle known as "staggers syndrome". (W824) |
| Symptoms | Tremorgenic mycotoxins affect central nervous system activity, inducing neurologic symptoms including mental confusion, paralysis, tremors, seizures, and death. They cause a neurological disease of cattle known as "staggers syndrome", which is characterized by muscle tremors and hyperexcitability. (W824) |
| Treatment | To control severe tremorscaused by tremorgenic mycotoxins, methocarbamol should be administered. Generalized seizures may be treated with diazepam followed by methocarbamol or a barbiturate such as pentobarbital sodium. Gastric lavage should be performed and activated charcoal administered to limit further absorption of toxins. (W825) |
| References | |
| General References |
|
Targets
1. Acetylcholinesterase
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Territrems act at the peripheral nerve endings as irreversible inhibitors of acetylcholinesterase. As acetylcholinesterase is needed to hydrolyze the neurotransmitter acetylcholine in cholinergic synapses, inhibition of this enzyme continually potentiates the acetylcholine-induced current of the neuron. It is thought that territrems inhibits acetylcholinesterase by becoming noncovalently trapped within the unique active-site gorge structure of the enzyme. (W886, W887)UniProt ID: P22303
Gene: ACHE
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report
References:
- W886 — Ling KH, Chiou CM, Tseng YL. Biotransformation of territrems by S9 fraction from rat liver. Drug Metab Dispos. 1991 May-Jun;19(3):587-95.
[1680623 ]
- W887 — Chen JW, Luo YL, Hwang MJ, Peng FC, Ling KH. Territrem B, a tremorgenic mycotoxin that inhibits acetylcholinesterase with a noncovalent yet irreversible binding mechanism. J Biol Chem. 1999 Dec 3;274(49):34916-23.
[10574966 ]