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Paspalitrem A

HCID 10028978
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Grundinformationen

CAS
63722-90-7
Standard-SMILES
CC(C)=CCc1ccc2[nH]c3c(c2c1)C[C@@H]1CC[C@@]2(O)C4=CC(=O)[C@@H]5O[C@@]4(CC[C@]2(C)[C@@]31C)OC5(C)C
InChIKey
WCISYVSWAOUFIY-TZHHUJIHSA-N
Summenformel
C32H39NO4
Durchschnittliche Molmasse
501,7 g/mol
Monoisotopische Masse
501,28790873

Überblick

Paspalitrem A is an organic heterotricyclic compound and an organooxygen compound.

Namen und Bezeichner

Bevorzugter Name
Paspalitrem A
IUPAC
(1S,4R,5S,16S,19S,23R)-19-hydroxy-4,5,24,24-tetramethyl-11-(3-methylbut-2-enyl)-25,26-dioxa-7-azaheptacyclo[21.2.1.01,20.04,19.05,16.06,14.08,13]hexacosa-6(14),8(13),9,11,20-pentaen-22-one

Namen und Synonyme

Paspalitrem AY875DQ8L6K(1S,4R,5S,16S,19S,23R)-19-hydroxy-4,5,24,24-tetramethyl-11-(3-methylbut-2-enyl)-25,26-dioxa-7-azaheptacyclo[21.2.1.01,20.04,19.05,16.06,14.08,13]hexacosa-6(14),8(13),9,11,20-pentaen-22-one(3R,5BS,7AS,13BS,13CR,15AS)-5B-HYDROXY-2,2,13B,13C-TETRAMETHYL-10-(3-METHYLBUT-2-EN-1-YL)-2,3,5B,6,7,7A,8,13,13B,13C,14,15-DODECAHYDRO-4H-3,15A-EPOXYOXEPINO(2'',3'':5',6')BENZO(1',2':6,7)INDENO(1,2-B)INDOL-4-ONE4H-3,15A-EPOXY-1-BENZOXEPINO(6',7':6,7)INDENO(1,2-B)INDOL-4-ONE, 2,3,5B,6,7,7A,8,13,13B,13C,14,15-DODECAHYDRO-5B-HYDROXY-2,2,13B,13C-TETRAMETHYL-10-(3-METHYL-2-BUTEN-1-YL)-, (3R,5BS,7AS,13BS,13CR,15AS)-63722-90-7(1S,4R,5S,16S,19S,23R)-19-hydroxy-4,5,24,24-tetramethyl-11-(3-methylbut-2-enyl)-25,26-dioxa-7-azaheptacyclo(21.2.1.01,20.04,19.05,16.06,14.08,13)hexacosa-6(14),8(13),9,11,20-pentaen-22-one19-hydroxy-4,5,24,24-tetramethyl-11-(3-methylbut-2-en-1-yl)-25,26-dioxa-7-azaheptacyclo(21.2.1.01,20.04,19.05,16.06,14.08,13)hexacosa-6(14),8(13),9,11,20-pentaen-22-one19-hydroxy-4,5,24,24-tetramethyl-11-(3-methylbut-2-en-1-yl)-25,26-dioxa-7-azaheptacyclo[21.2.1.01,20.04,19.05,16.06,14.08,13]hexacosa-6(14),8(13),9,11,20-pentaen-22-oneRefChem:170147CHEMBL4555220

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,1
Polarare Oberfläche (TPSA)
71,6 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
2
Schwere Atome
37
Formalladung
0
Komplexität
1.090

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Toxikologische Informationen

Treatment · 1 Eintrag

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 · 1 Eintrag

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. In addition, paspalitrem A inhibits presynaptic high-conductance Ca+2 activated maxi-K+ channels in the smooth muscle. (A2976, A2993)

Signs and Symptoms · 1 Eintrag

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).

Chemie und Industrie

Verwendung und Herstellung

UsesPaspalitrem A is a tremorgenic mycotoxin that has been found in fungi of the genera Penicillium and Aspergillus. It may be found in contaminated cereal crops such as oats, barley, millet, corn and rice. (A2976)

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
CHEBI:210797

Datenbank-Bezeichner

CAS
63722-90-7
PubChem CID
10028978
ChEMBL
CHEMBL4555220
ChEBI
CHEBI:210797
UNII
Y875DQ8L6K
Nikkaji
J2.411.020F