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Wortmannin

Wortmannin structure

CAS No:
19545-26-7
Formula:
C23H24O8
Chemical Name:
Wortmannin
Synonyms:
3H-Furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione,11-(acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-,(1S,6bR,9aS,11R,11bR)-;3H-Furo[4,3,2-de]indeno[4,5-h]-2-benzopyran-3,6,9-trione,11-(acetyloxy)-1,6b,7,8,9a,10,11,11b-octahydro-1-(methoxymethyl)-9a,11b-dimethyl-,[1S-(1α,6bα,9aβ,11α,11bβ)]-;(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;Wortmannin;KY 12420;(+)-Wortmannin;1405-03-4
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

White to pale yellow powder

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.|Wortmannin is a steroid metabolite of Penicillium funiculosum and Talaromyces wortmannii fungi. This drug acts as a nonspecific, covalent inhibitor of phosphoinositide 3-kinase enzymes (PI3Ks).|Wortmannin is a potent fungal metabolite isolated from Penicillium wortmannin that selectively inhibits phosphatidylinositol 3-kinase and affects the signal transduction pathway. (NCI)|An androstadiene metabolite produced by the fungi PENICILLIUM funiculosum that inhibits PHOSPHATIDYLINOSITOL-3-KINASES and alloantigen-specific activation of T-LYMPHOCYTES in human tumor cell lines. It is widely used in CELL BIOLOGY research and has broad therapeutic potential.

Wortmannin Basic Attributes

Molecular Weight：

428.43

Exact Mass：

428.43

EC Number：

214-538-0

UNII：

XVA4O219QW

NSC Number：

627609|221019

DSSTox ID：

DTXSID8040642

NCI Thesaurus Code：

C1277

HScode：

29322090

Characteristics

PSA：

109

XLogP3：

1.2

Appearance：

off-white powder

Density：

1.2454 (rough estimate)

Melting Point：

240 °C

Boiling Point：

463.31°C (rough estimate)

Flash Point：

2℃

Refractive Index：

1.4480 (estimate)

Water Solubility：

DMSO: soluble

Storage Conditions：

2-8°C

Safety Information

Packing level：

Hazard category：

6.1

Transport codes：

UN 3462 6.1/PG 1

wgk germany：

hazard class code：

26/27/28-36/37/38-36-20/21/22-11

safety instructions：

28-36/37-45-37/39-26-16

RTECS Number：

CB9641000

Marks：

T+,T,Xi,Xn,F

Precautionary statement(s)：

P260-P264-P280-P284-P302 + P350-P310

Hazard Statements：

H300-H310-H330

GHS Classification：

|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|P260, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P304+P340, P310, P320, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 43 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

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. (See all compounds classified as Immunosuppressive Agents.)|Compounds which inhibit or antagonize the biosynthesis or action of insulin. (See all compounds classified as Insulin Antagonists.)|Agents that inhibit PROTEIN KINASES. (See all compounds classified as Protein Kinase Inhibitors.)|Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells. (See all compounds classified as Radiation-Sensitizing Agents.)|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. (See all compounds classified as Antifungal Agents.)

MeSH Entry Terms：

MS 54

Wortmannin Use and Manufacturing

Wortmannin 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 antitumor 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.

Computed Properties

Molecular Weight:428.4
XLogP3:1.2
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:4
Exact Mass:428.14711772
Monoisotopic Mass:428.14711772
Topological Polar Surface Area:109
Heavy Atom Count:31
Complexity:921
Defined Atom Stereocenter Count:5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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