Wortmannin

HCID 312145
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Grundinformationen

CAS
19545-26-7
Standard-SMILES
COC[C@H]1OC(=O)c2coc3c2[C@@]1(C)C1=C(C3=O)[C@@H]2CCC(=O)[C@@]2(C)C[C@H]1OC(C)=O
InChIKey
QDLHCMPXEPAAMD-QAIWCSMKSA-N
Summenformel
C23H24O8
Durchschnittliche Molmasse
428,4 g/mol
Monoisotopische Masse
428,14711773

Überblick

Wortmannin is a delta-lactone, an organic heteropentacyclic compound, a cyclic ketone and an acetate ester. It has a role as a radiosensitizing agent, an anticoronaviral agent, a geroprotector, an antineoplastic agent, an EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor, a Penicillium metabolite and an autophagy inhibitor.

Namen und Bezeichner

Bevorzugter Name
Wortmannin
IUPAC
[(1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.02,10.05,9.015,19]nonadeca-2(10),12(19),14-trien-3-yl] acetate
Englischer Name
WORTMANNIN
Summenformel
C23H24O8
Molmasse
428.43

Namen und Synonyme

wortmannin19545-26-7WartmanninAntibiotic SL-2052SL-2052XVA4O219QWNSC221019DTXSID8040642NSC-627609CHEBI:52289NSC627609(1S,6bR,9aS,11R,11bR)-11-(Acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-3H-furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione
Weitere Namen anzeigen
CS-731KY 1242KY 12420WortmamminWortmannin,98%WORTMANNINTOXINKY-12420antibioticsl-2052
[(1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.02,10.05,9.015,19]nonadeca-2(10),12(19),14-trien-3-yl] acetate(1S,6bR,9aS,11R,11bR)-9a,11b-dimethyl-1-[(methyloxy)methyl]-3,6,9-trioxo-1,6,6b,7,8,9,9a,10,11,11b-decahydro-3H-furo[4,3,2-de]indeno[4,5-h]isochromen-11-yl acetateMS54MS-54((1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo(10.6.1.02,10.05,9.015,19)nonadeca-2(10),12(19),14-trien-3-yl) acetate(1S,6bR,9aS,11R,11bR)-11-(Acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-3H-furo(4,3,2-de)indeno(4,5-h)-2-benzopyran-3,6,9-trione(1S,6bR,9aS,11R,11bR)-9a,11b-dimethyl-1-((methyloxy)methyl)-3,6,9-trioxo-1,6,6b,7,8,9,9a,10,11,11b-decahydro-3H-furo(4,3,2-de)indeno(4,5-h)isochromen-11-yl acetateRefChem:389363

Datenbank-Bezeichner

CAS
19545-26-7
PubChem CID
312145
DTXSID
DTXSID8040642
ChEMBL
CHEMBL428496
ChEBI
CHEBI:52289
UNII
XVA4O219QW
EC Number
606-337-5
Nikkaji
J13.549F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,2
Polarare Oberfläche (TPSA)
109 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
8
Frei drehbare Bindungen
4
Schwere Atome
31

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

Physikochemische Eigenschaften

Schmelzpunkt
234 · 234-240 °C
Siedepunkt
463.31 °C · 463.31°C (rough estimate)
Dichte
1.2454 · 1.2454 (rough estimate)
Brechungsindex
1.448 · 1.4480 (estimate)
Flammpunkt
2 ℃ · 2℃
storage temp.
-20 °C · -20°C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 44 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 2 (100%)

Sicherheitsdaten

F
3-8-10
wgk
3
ridadr
UN 3462 6.1/PG 1
hs_code
29322090
RTECS-Nr.
CB9641000
risk_code
26/27/28-36/37/38-36-20/21/22-11

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 5 Einträge

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging.

Compounds which inhibit or antagonize the biosynthesis or action of insulin.

Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells.

Agents that inhibit PROTEIN KINASES.

Anwendungen · 1 Eintrag

VerwendenWortmannin is a steroidal metabolite belonging to the viridin group, isolated from Penicillium wortmannii in 1957. The structure was finally solved in 1968. Wortmannin exhibits broad spectrum antifungal activity, together with antitumour and antiinflammatory activity. Wortmannin is a potent inhibitor of phosphoinositide 3-kinase and myosin light chain kinase. Wortmannin also activates neutrophil and formyl-Met-Leu-Phe-mediated phospholipase D, inhibits autophagy, potentiates LPS-induced NO production and induces Alzheimer-like hyperphosphorylation in tau in vivo.

Vor- und nachgelagerte Produkte

Anbieter100 Anbieter

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]

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