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Fumitremorgin A

HCID 107713
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
12626-18-5
Standard-SMILES
COc1ccc2c3c4n(c2c1)[C@@H](C=C(C)C)OOC(C)(C)C[C@@H]4N1C(=O)[C@@H]2CCCN2C(=O)[C@]1(O)[C@H]3OCC=C(C)C
InChIKey
ACGHJVZDNQZJOV-BMOJZYMJSA-N
Summenformel
C32H41N3O7
Durchschnittliche Molmasse
579,7 g/mol
Monoisotopische Masse
579,29445066

Überblick

Fumitremorgin A is an organic heterohexacyclic compound that is a mycotoxic indole alkaloid obtained by prenylation of the 10-hydroxy group of verruculogen. It has a role as a mycotoxin. It is a diol, an organic peroxide, an aromatic ether, an indole alkaloid and an organic heterohexacyclic compound. It is functionally related to a verruculogen.

Namen und Bezeichner

Bevorzugter Name
Fumitremorgin A
IUPAC
(9R,14S,17S,23R,24S)-23-hydroxy-5-methoxy-12,12-dimethyl-24-(3-methylbut-2-enoxy)-9-(2-methylprop-1-enyl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.02,7.08,25.015,23.017,21]pentacosa-1(25),2(7),3,5-tetraene-16,22-dione
Englischer Name
Fumitremorgin A
Summenformel
C32H41N3O7
Molmasse
579.68

Namen und Synonyme

Fumitremorgin A12626-18-5ZR1C7949XTCHEBI:72766DTXSID30925479(9R,14S,17S,23R,24S)-23-hydroxy-5-methoxy-12,12-dimethyl-24-(3-methylbut-2-enoxy)-9-(2-methylprop-1-enyl)-10,11-dioxa-8,15,21-triazahexacyclo[12.10.1.02,7.08,25.015,23.017,21]pentacosa-1(25),2(7),3,5-tetraene-16,22-dione(5R,10S,10aR,14aS,15bS)-10a-hydroxy-7-methoxy-2,2-dimethyl-10-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylprop-1-en-1-yl)-1,10,10a,14,14a,15b-hexahydro-12H-3,4-dioxa-5a,11a,15a-triazacycloocta[1,2,3-lm]indeno[5,6-b]fluorene-11,15(H,13H)-dione(5R,10S,10aR,14aS,15bS)-10a-hydroxy-7-methoxy-2,2-dimethyl-10-((3-methylbut-2-en-1-yl)oxy)-5-(2-methylprop-1-en-1-yl)-1,10,10a,14,14a,15b-hexahydro-12H-3,4-dioxa-5a,11a,15a-triazacycloocta(1,2,3-lm)indeno(5,6-b)fluorene-11,15(H,13H)-dione(9R,14S,17S,23R,24S)-23-hydroxy-5-methoxy-12,12-dimethyl-24-(3-methylbut-2-enoxy)-9-(2-methylprop-1-enyl)-10,11-dioxa-8,15,21-triazahexacyclo(12.10.1.02,7.08,25.015,23.017,21)pentacosa-1(25),2(7),3,5-tetraene-16,22-dioneRefChem:921909DTXCID20135430723-hydroxy-5-methoxy-12,12-dimethyl-24-((3-methylbut-2-en-1-yl)oxy)-9-(2-methylprop-1-en-1-yl)-10,11-dioxa-8,15,21-triazahexacyclo(12.10.1.02,7.08,25.015,23.017,21)pentacosa-1(25),2(7),3,5-tetraene-16,22-dione

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,8
Polarare Oberfläche (TPSA)
103 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
7
Frei drehbare Bindungen
5
Schwere Atome
42
Formalladung
0
Komplexität
1.150

Physikochemische Eigenschaften

Siedepunkt
762.1 · 762.1±60.0 °C(Predicted)
Dichte
1.34 · 1.34±0.1 g/cm3(Predicted)
pka
10.53 · 10.53±0.70(Predicted)

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. (A2974, A2975, A2976)

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 and hyperexcitability. Fumitremorgin A exposure has also been shown to cause bradycardia, arrhythmia, and hypertension. (A2974, A3025)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Chemie und Industrie

Verwendung und Herstellung

UsesFumitremorgin A (FTA) is mycotoxin isolated from Aspergillus fumigatus. (A3024)

Anwendungen

OccurrenceA tremorgenic toxin isolated as a metabolite of AspergillusJurnigatus. It is highly toxic.

Anbieter6 Anbieter

成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
青岛贞开生物医药技术有限公司0532-58268781 18561687109 · [email protected]
ATK CHEMICAL COMPANY LIMITED+undefined-21-51877795 · [email protected]
四川恒诚致远生物科技有限公司18113192475 18113192475 · [email protected]
上海禾午生物科技有限公司021-57886085 17317861055 · [email protected]
武汉丽合智造生物科技有限公司18971458902 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: An organic heterohexacyclic compound that is a mycotoxic indole alkaloid obtained by prenylation of the 10-hydroxy group of verruculogen.

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Weitere Namen anzeigen
FUMITREMORGENAA Fumitremorgin AFumitremorgin A / Fumitremorgen A5H,12H-3,4-Dioxa-5a,11a,15a-triazacyclooct[lm]indeno[5,6-b]fluorene-11,15(2H,13H)-dione, 1,10,10a,14,14a,15b-hexahydro-10a-hydroxy-7-methoxy-2,2-dimethyl-10-[(3-methyl-2-buten-1-yl)oxy]-5-(2-methyl-1-propen-1-yl)-, (5R,10S,10aR,14aS,15bS)-
UNII-ZR1C7949XTFUMITREMORGEN ASCHEMBL1887086ACon1_001759BRD8008BRD-8008NCGC00180170-01NCGC00180170-02

Datenbank-Bezeichner

CAS
12626-18-5
PubChem CID
107713
DTXSID
DTXSID30925479
ChEBI
CHEBI:72766
UNII
ZR1C7949XT
Nikkaji
J152.196I