Basic information
- CAS
90986-52-0- Standard SMILES
CC(=O)O[C@@H]1C=C2[C@H](CC[C@@]3(C)[C@@]2(O)CC[C@H]2Cc4c([nH]c5cc6c(cc45)[C@@H](O)[C@H]4C6=CC(C)(C)OC4(C)C)[C@@]23C)O[C@@H]1C(C)(C)O- InChIKey
SHMYDSYGDWIPKT-WWVOELFWSA-N- Molecular formula
- C39H51NO7
- Average molar mass
- 645.8 g/mol
- Monoisotopic mass
- 645.36655297
Overview
Janthitrem F is produced by Penicillium janthinellum. Tremorgenic mycotoxin Janthitrem F belongs to the family of Diterpenes. These are terpene compounds formed by four isoprene units.
Names & identifiers
- Preferred name
- Janthitrem F
- IUPAC
- [(2S,3R,6S,8S,9R,12S,15S,21S,22R)-12,21-dihydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo[15.14.0.02,15.03,12.06,11.018,30.020,28.022,27]hentriaconta-1(17),10,18,20(28),26,29-hexaen-9-yl] acetate
Names & synonyms
Janthitrem FJanthitrem E monoacetate90986-52-0RefChem:108788812,21-dihydroxy-8-(2-hydroxypropan-2-yl)-2,3,23,23,25,25-hexamethyl-7,24-dioxa-31-azaoctacyclo(15.14.0.02,15.03,12.06,11.018,30.020,28.022,27)hentriaconta-1(17),10,18(30),19,26,28-hexaen-9-yl acetate(2s,3r,4bs,6as,9s,9ar,15bs,15cr,17as)-4b,9-dihydroxy-2-(2-hydroxypropan-2-yl)-10,10,12,12,15b,15c-hexamethyl-3,4b,5,6,6a,7,9,9a,10,12,15,15b,15c,16,17,17a-hexadecahydro-2h-chromeno[5',6':6,7]indeno[1,2-b]pyrano[4',3':3,4]cyclopenta[1,2-f]indol-3-yl acetatDTXSID70920024HY-N7222AKOS040752157CS-0105856(2S,3R,4bS,6aS,9S,9aR,15bS,15cR,17aS)-4b,9-Dihydroxy-2-(2-hydroxypropan-2-yl)-10,10,12,12,15b,15c-hexamethyl-3,4b,5,6,6a,7,9,9a,10,12,15,15b,15c,16,17,17a-hexadecahydro-2H-[1]benzopyrano[5',6':6,7]indeno[1,2-b]pyrano[4',3':3,4]cyclopenta[1,2-f]indol-3-yl acetate4b,9-Dihydroxy-2-(2-hydroxypropan-2-yl)-10,10,12,12,15b,15c-hexamethyl-3,4b,5,6,6a,7,9,9a,10,12,15,15b,15c,16,17,17a-hexadecahydro-2H-[1]benzopyrano[5',6':6,7]indeno[1,2-b]pyrano[4',3':3,4]cyclopenta[1,2-f]indol-3-yl acetate
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 3.1
- Topological polar surface area
- 121 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 47
- Formal charge
- 0
- Complexity
- 1,420
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
Treatment
To control severe tremors caused 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. (A744)
Health EffectsTremorgenic mycotoxins affect central nervous system activity. They cause a neurological disease of cattle known as "staggers syndrome". (A2976)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary
Tremorgenic mycotoxins exert their toxic effects by interfering with neurotransmitter release, possibly by causing degeneration of nerve terminals. They are thought to inhibit gamma-aminobutyric acid (GABA) receptors, both pre- and postsynaptic, as well as inhibit transmitter breakdown at the GABA-T receptors. This would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, then lead to decreased levels of neurotransmitter in the synapse. (A2976)
Signs and 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, hyperexcitability, convulsions and ataxia. (A2976)
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Chemistry & industry
Uses & manufacturing
UsesJanthitrems are tremorgenic mycotoxins that have been found in the fungus Penicillium janthinellum. They may be found in contaminated cereal crops such as oats, barley, millet, corn and rice. (A2976, A3065)
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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