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WORTMANNIN structure
WORTMANNIN structure

WORTMANNIN

CAS No.: 19545-26-7
Molecular Weight:428.437
Modify Date.: 2022-11-07 12:07
Introduction: 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 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. View more+
1. Names and Identifiers
1.1 Name
WORTMANNIN
1.2 Synonyms

(+)-Wortmannin (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,11S,11bR)-1-(Methoxymethyl)-9a,11b-dimethyl-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 acetate [1S-(1ALPHA,6BALPHA,9ABETA,11ALPHA,11BBETA)]-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 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,6bR,9aS,11S,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)]- antibioticsl-2052 KY 1242 KY 12420 sl-2052 Wortmannin KY 1242 Wortmannin (+)-Wortmannin Wortmannin from Talaromyces (Penicillium)

1.3 CAS No.
19545-26-7
1.4 CID
312145
1.5 EINECS(EC#)
606-337-5
1.6 Molecular Formula
C23H24O8 (isomer)
1.7 Inchi
InChI=1S/C23H24O8/c1-10(24)30-13-7-22(2)12(5-6-14(22)25)16-18(13)23(3)15(9-28-4)31-21(27)11-8-29-20(17(11)23)19(16)26/h8,12-13,15H,5-7,9H2,1-4H3/t12-,13+,15+,22-,23-/m0/s1
1.8 InChkey
QDLHCMPXEPAAMD-QAIWCSMKSA-N
1.9 Canonical Smiles
CC(=O)OC1CC2(C(CCC2=O)C3=C1C4(C(OC(=O)C5=COC(=C54)C3=O)COC)C)C
1.10 Isomers Smiles
CC(=O)O[C@@H]1C[C@]2([C@@H](CCC2=O)C3=C1[C@]4([C@H](OC(=O)C5=COC(=C54)C3=O)COC)C)C
2. Properties
2.1 Density
1.39
2.1 Melting point
234-240 °C
2.1 Boiling point
615.6 °C at 760 mmHg
2.1 Refractive index
1.591
2.1 Flash Point
326.1 °C
2.1 Precise Quality
428.14700
2.1 PSA
109.11000
2.1 logP
2.53640
2.1 Solubility
几乎不溶 (0.051 g/L) (25 oC),
2.2 Λmax
296nm(lit.)
2.3 Appearance
White solid
2.4 Storage
2-8°C
2.5 Chemical Properties
White to pale yellow powder
2.6 Color/Form
off-white
2.7 Water Solubility
DMSO: soluble
2.8 StorageTemp
2-8°C
3. Use and Manufacturing
3.1 GHS Classification
Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 27 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H300+H310+H330 (11.11%): Fatal if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
H310 (100%): Fatal in contact with skin [Danger Acute toxicity, dermal]
H330 (100%): Fatal if inhaled [Danger Acute toxicity, inhalation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
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
3.2 Usage
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 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.
4. Safety and Handling
4.1 Hazard Codes
T+
4.1 Risk Statements
R26/27/28
4.1 Safety Statements
28-36/37-45
4.1 Packing Group
I
4.1 Hazard Class
6.1
4.1 RIDADR
UN 3462
4.1 WGK Germany
3
4.1 RTECS
CB9641000
5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 1

Acute toxicity - Dermal, Category 2

Acute toxicity - Inhalation, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H300 Fatal if swallowed

H310 Fatal in contact with skin

H330 Fatal if inhaled

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P262 Do not get in eyes, on skin, or on clothing.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.

P284 [In case of inadequate ventilation] wear respiratory protection.

Response

P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P330 Rinse mouth.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P310 Immediately call a POISON CENTER/doctor/\u2026

P361+P364 Take off immediately all contaminated clothing and wash it before reuse.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P320 Specific treatment is urgent (see ... on this label).

Storage

P405 Store locked up.

P403+P233 Store in a well-ventilated place. Keep container tightly closed.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

7. Other Information
7.0 Usage
Wortmannin 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.
7.1 Merck
14,10053
7.2 BRN
67676
7.3 Chemical Properties
White to pale yellow powder
7.4 Uses
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 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.
7.5 Uses
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.
7.6 Biological Activity
Potent, selective, cell-permeable and irreversible inhibitor of phosphatidylinositol 3-kinase (PI 3-kinase) (IC 50 = 2-4 nM). Also potently inhibits polo-like kinase 1 (PLK1) (IC 50 = 5.8 nM).
8. Computational chemical data
  • Molecular Weight: 428.437g/mol
  • Molecular Formula: C23H24O8
  • Compound Is Canonicalized: True
  • XLogP3-AA: 1.2
  • Exact Mass: 428.14711772
  • Monoisotopic Mass: 428.14711772
  • Complexity: 921
  • Rotatable Bond Count: 4
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 8
  • Topological Polar Surface Area: 109
  • Heavy Atom Count: 31
  • Defined Atom Stereocenter Count: 5
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADceB4PAAAAAAAAAAAAAAAAAAAAaIAAAAkQIAAAAAAAEjBgAAAGgAAAAAADxSgmAIiDIAABECIAojSiAICCAAkIAAAiAFECMgNJzaMNB6CGWCl4BEKqYfL7vzvgAAAAAAAAAAAAAAAAAAAAAAACAAAAA==
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10. Realated Product Infomation