CAS 19545-26-7 Wortmannin (HCID 312145)

Overview

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.

Names & identifiers

Preferred 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
English name: WORTMANNIN
Molecular formula: C23H24O8
Molecular weight: 428.43

Names & synonyms

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

Show more names

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

Database identifiers

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

Properties

Computed structural properties

XLogP: 1.2
Topological polar surface area: 109 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 8
Rotatable bonds: 4
Heavy atoms: 31
Formal charge: 0
Complexity: 921

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Physicochemical properties

Melting point: 234 · 234-240 °C
Boiling point: 463.31 °C · 463.31°C (rough estimate)
alpha: 80 · +80.0~+105.0゜(20℃/D)(c=0.1,C2H5OH)
Density: 1.2454 · 1.2454 (rough estimate)
refractive index: 1.448 · 1.4480 (estimate)
Flash point: 2 ℃ · 2℃
storage temp.: -20 °C · -20°C
solubility: DMSO: soluble
form: powder
color: off-white
biological source: Penicillium funiculosum
λmax: 296 nm · 296nm(lit.)
Sensitive: Light Sensitive
Merck: 14 · 14,10053
BRN: 67676 · 67676
Stability: 1 year · Stable for 1 year from date of purchase as supplied. Dried aliquots evaporated from ethanol may be stored at -20° for several months. Solutions however are not stable and must be used within one working day. Note
InChIKey: QDLHCMPXEPAAMD-QAIWCSMKSA-N
SMILES: [o]1c2c3c(c1)C(=O)O[C@@H]([C@@]3(C4=C([C@H]5[C@](C[C@H]4OC(=O)C)(C(=O)CC5)C)C2=O)C)COC
FDA UNII: 4 O219QW · XVA4O219QW
UNSPSC Code: 12352200 · 12352200
NACRES: 77 · NA.77
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements: 300 · H300+H310+H330
Precautionary statements: 262 · P262-P280-P301+P310+P330-P302+P352+P310-P304+P340+P310
Hazard Codes: T+,T,Xi,Xn,F
Risk Statements: 26 · 26/27/28-36/37/38-36-20/21/22-11
Safety Statements: 28 · 28-36/37-45-37/39-26-16
RIDADR: 3462 · UN 3462 6.1/PG 1
WGK Germany: 3 · 3
RTECS: 9641000 · CB9641000
F: 3 · 3-8-10
HazardClass: 6.1 · 6.1
PackingGroup: I
HS Code: 29322090 · 29322090
Storage Class: 6.1 A · 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications: 1 InhalationAcute · Acute Tox. 1 InhalationAcute Tox. 1 OralAcute Tox. 2 Dermal

Safety & regulation

GHS classification

GHS Classification · 4 items

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.

Hazard information

Hazard Classes and CategoriesAcute Tox. 2 (100%)

Safety data

F: 3-8-10
wgk: 3
rtecs: CB9641000
ridadr: UN 3462 6.1/PG 1
hs_code: 29322090
risk_code: 26/27/28-36/37/38-36-20/21/22-11
Signal word: Danger
Symbol(GHS): GHS06
hazard_code: T+,T,Xi,Xn,F
safety_code: 28-36/37-45-37/39-26-16
hazard_class: 6.1
Storage Class: 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
packing_group: I
Hazard statements: H300+H310+H330
Hazard Classifications: Acute Tox. 1 InhalationAcute Tox. 1 OralAcute Tox. 2 Dermal
Precautionary statements: P262-P280-P301+P310+P330-P302+P352+P310-P304+P340+P310

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 5 items

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.

Applications · 4 items

DescriptionWortmannin (19545-26-7) is a potent and selective inhibitor of PI3-kinase which acts via covalent modification of Lys-802.2Inhibits autophagy in rat hepatocytes.3Inhibits adipocyte differentiation of 3T3-L1 cells.4Wortmannin is useful tool for probing PI3-K-mediated cellular events.5

UsesWortmannin 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.

UsesWortmannin is used as inhibitor of phosphatidylinositol 3-kinase, used cell biology reagent that has been used previously in research to inhibit DNA repair, receptor-mediated endocytosis and cell proliferation. It inhibits fMLP induced PIP3 and superoxide anion production in guinea pig neutrophils. It blocks insulin metabolic effects in rat adipocytes without affecting the insulin receptor tyrosine kinase activity.

UsesWortmannin, Ready Made Solution has been used: as a phosphoinositide 3-kinase (PI3K) pathway inhibitoras an endoderm-inducing agent in stem cell selection and differentiation as a autophagy inhibitor

Upstream & downstream products

Upstream raw materials

3H-Furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione, 1,6b,7,8,9a,10,11,11b-octahydro-11-hydroxy-1-(methoxymethyl)-9a,11b-dimethyl-, (1S,6bR,9aS,11R,11bR)-Androst-4-ene-3,17-dione, 9,11-epoxy-, (11α)-17β-hydroxy Wortmannin

Suppliers100 total

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]

Additional notes · 1 item

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