wortmannin (CHEBI:52289)

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CHEBI:52289 - wortmannin

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ChEBI Name	wortmannin

ChEBI ID	CHEBI:52289

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Sandra Orchard

Secondary ChEBI IDs	CHEBI:43674

Supplier Information	ChemicalBook:CB7241293, eMolecules:533310, Selleckchem:wortmannin, ZINC000001619592

Download	Molfile XML SDF

more structures >>

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The Resolver thinks Mol

KWT - Ideal conformer

Mrv1927 10282111103D

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Time for openFile(KWT - Ideal conformer

Mrv1927 10282111103D

55 59 0 0 0 0 999 V2000

0.9950 -0.2240 1.9290 C 0 0 1 0 0 0 0 0 0 0 0 0

0.7910 -0.5540 3.3300 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.1050 -0.7940 1.0370 C 0 0 1 0 0 0 0 0 0 0 0 0

0.9730 1.3020 1.8270 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.4230 -0.8070 3.8930 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.5450 -1.3680 4.9640 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.5760 -0.3480 3.0920 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.3820 -0.3360 1.6820 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.8380 0.0960 3.2880 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.4920 0.1710 1.1140 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.4620 0.3590 -0.3410 C 0 0 0 0 0 0 0 0 0 0 0 0

-3.3810 0.3980 2.0830 O 0 0 0 0 0 0 0 0 0 0 0 0

-3.4720 0.6330 -0.9670 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.1370 0.1940 -0.9990 C 0 0 0 0 0 0 0 0 0 0 0 0

2.3270 0.1180 -0.4340 O 0 0 0 0 0 0 0 0 0 0 0 0

1.2440 -0.5500 -1.1350 C 0 0 1 0 0 0 0 0 0 0 0 0

3.5730 -0.3750 -0.4950 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.0590 -0.3340 -0.4020 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.0340 0.6790 -2.4070 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.0490 -2.3250 1.0850 C 0 0 0 0 0 0 0 0 0 0 0 0

1.2770 -0.0600 -2.5820 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.0910 -0.2610 -3.1940 C 0 0 1 0 0 0 0 0 0 0 0 0

-0.5320 -1.7190 -3.0790 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2740 0.2020 -4.6130 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.3000 0.6410 -3.2650 C 0 0 1 0 0 0 0 0 0 0 0 0

-1.7320 0.6420 -4.7120 C 0 0 2 0 0 0 0 0 0 0 0 0

0.5590 0.2220 -5.4840 O 0 0 0 0 0 0 0 0 0 0 0 0

3.7940 -1.3770 -1.1330 O 0 0 0 0 0 0 0 0 0 0 0 0

4.6960 0.3180 0.2300 C 0 0 0 0 0 0 0 0 0 0 0 0

1.9820 1.8510 2.6760 O 0 0 0 0 0 0 0 0 0 0 0 0

1.9110 3.2720 2.5370 C 0 0 0 0 0 0 0 0 0 0 0 0

1.9560 -0.6040 1.6250 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.0030 1.6720 2.1380 H 0 0 0 0 0 0 0 0 0 0 0 0

1.1630 1.6000 0.7960 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.3310 0.1970 4.2440 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4700 -1.6210 -1.1350 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.6260 1.6950 -2.4080 H 0 0 0 0 0 0 0 0 0 0 0 0

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-0.9020 -2.7370 0.5450 H 0 0 0 0 0 0 0 0 0 0 0 0

0.8750 -2.6700 0.6230 H 0 0 0 0 0 0 0 0 0 0 0 0

1.5460 0.9980 -2.6070 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0220 -0.6300 -3.1450 H 0 0 0 0 0 0 0 0 0 0 0 0

0.1880 -2.3570 -3.5910 H 0 0 0 0 0 0 0 0 0 0 0 0

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5.6260 -0.2240 0.0650 H 0 0 0 0 0 0 0 0 0 0 0 0

4.7980 1.3360 -0.1450 H 0 0 0 0 0 0 0 0 0 0 0 0

4.4760 0.3460 1.2970 H 0 0 0 0 0 0 0 0 0 0 0 0

2.6670 3.7370 3.1700 H 0 0 0 0 0 0 0 0 0 0 0 0

2.0900 3.5440 1.4970 H 0 0 0 0 0 0 0 0 0 0 0 0

0.9220 3.6170 2.8390 H 0 0 0 0 0 0 0 0 0 0 0 0

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3 8 1 0 0 0 0

3 18 1 0 0 0 0

3 20 1 6 0 0 0

4 30 1 0 0 0 0

4 33 1 0 0 0 0

4 34 1 0 0 0 0

5 6 2 0 0 0 0

5 7 1 0 0 0 0

7 8 1 0 0 0 0

7 9 2 0 0 0 0

8 10 2 0 0 0 0

9 12 1 0 0 0 0

9 35 1 0 0 0 0

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10 12 1 0 0 0 0

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14 19 1 0 0 0 0

15 16 1 0 0 0 0

15 17 1 0 0 0 0

16 18 1 0 0 0 0

16 21 1 0 0 0 0

16 36 1 6 0 0 0

17 28 2 0 0 0 0

17 29 1 0 0 0 0

19 22 1 0 0 0 0

19 25 1 0 0 0 0

19 37 1 1 0 0 0

20 38 1 0 0 0 0

20 39 1 0 0 0 0

20 40 1 0 0 0 0

21 22 1 0 0 0 0

21 41 1 0 0 0 0

21 42 1 0 0 0 0

22 23 1 6 0 0 0

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29 50 1 0 0 0 0

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29 52 1 0 0 0 0

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31 53 1 0 0 0 0

31 54 1 0 0 0 0

31 55 1 0 0 0 0

M END): 16 ms

reading 55 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

Default Van der Waals type for model set to Babel

55 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

Script completed

Jmol script terminated

Molfile expand

Molfile

Wikipedia	License
Wortmannin, a steroid metabolite of the fungi Penicillium funiculosum, Talaromyces wortmannii, is a non-specific, covalent inhibitor of phosphoinositide 3-kinases (PI3Ks). It has an in vitro inhibitory concentration (IC50) of around 5 nM, making it a more potent inhibitor than LY294002, another commonly used PI3K inhibitor. It displays a similar potency in vitro for the class I, II, and III PI3K members although it can also inhibit other PI3K-related enzymes such as mTOR, DNA-PKcs, some phosphatidylinositol 4-kinases, myosin light chain kinase (MLCK) and mitogen-activated protein kinase (MAPK) at high concentrations Wortmannin has also been reported to inhibit members of the polo-like kinase family with IC50 in the same range as for PI3K. The half-life of wortmannin in tissue culture is about 10 minutes due to the presence of the highly reactive C20 carbon that is also responsible for its ability to covalently inactivate PI3K. Wortmannin is a commonly used cell biology reagent that has been used previously in research to inhibit DNA repair, receptor-mediated endocytosis and cell proliferation.
Read full article at Wikipedia

Formula

C23H24O8

Net Charge

Average Mass

428.437

Monoisotopic Mass

428.14712

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

InChIKey

QDLHCMPXEPAAMD-QAIWCSMKSA-N

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)C[C@@H](OC(C)=O)C1=C2C(=O)C2=C3C(=CO2)C(=O)O[C@H](COC)[C@]13C

Roles Classification
Biological Role(s):	EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor An inhibitor of phosphatidylinositol 3-kinase, EC 2.7.1.137, a family of related enzymes capable of phosphorylating the 3 position hydroxy group of the inositol ring of a phosphatidylinositol. anticoronaviral agent Any antiviral agent which inhibits the activity of coronaviruses. autophagy inhibitor Any compound that inhibits the process of autophagy (the self-digestion of one or more components of a cell through the action of enzymes originating within the same cell). Penicillium metabolite Any fungal metabolite produced during a metabolic reaction in Penicillium.

Application(s):	geroprotector Any compound that supports healthy aging, slows the biological aging process, or extends lifespan. radiosensitizing agent A drug that makes increases the sensitivity of tumour cells to radiation therapy. antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	wortmannin (CHEBI:52289) has role Penicillium metabolite (CHEBI:76964) wortmannin (CHEBI:52289) has role anticoronaviral agent (CHEBI:149553) wortmannin (CHEBI:52289) has role antineoplastic agent (CHEBI:35610) wortmannin (CHEBI:52289) has role autophagy inhibitor (CHEBI:88230) wortmannin (CHEBI:52289) has role EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor (CHEBI:50914) wortmannin (CHEBI:52289) has role geroprotector (CHEBI:176497) wortmannin (CHEBI:52289) has role radiosensitizing agent (CHEBI:132992) wortmannin (CHEBI:52289) is a δ-lactone (CHEBI:18946) wortmannin (CHEBI:52289) is a acetate ester (CHEBI:47622) wortmannin (CHEBI:52289) is a cyclic ketone (CHEBI:3992) wortmannin (CHEBI:52289) is a organic heteropentacyclic compound (CHEBI:38164)

Incoming	PX-866 (CHEBI:65345) has functional parent wortmannin (CHEBI:52289)

IUPAC Name

(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 acetate

Synonym	Source
Wartmannin	ChemIDplus

Manual Xrefs	Databases
C00023672	KNApSAcK
C15181	KEGG COMPOUND
CPD-11924	MetaCyc
DB08059	DrugBank
HMDB0259902	HMDB
KWT	PDBeChem
LSM-3947	LINCS
Wortmannin	Wikipedia
View more database links

Registry Numbers	Types	Sources
19545-26-7	CAS Registry Number	ChemIDplus
67676	Reaxys Registry Number	Reaxys

Citations

Turkoz Uluer E, Kilicaslan Sonmez P, Akogullari D, Onal M, Tanriover G, Inan S (2021)
Do Wortmannin and Thalidomide induce apoptosis by autophagy inhibition in 4T1 breast cancer cells in vitro and in vivo?
American journal of translational research 13, 6236-6247 [PubMed:34306363]
[show Abstract]

Ihara M, Shichijo K, Takeshita S, Kudo T (2020)
Wortmannin, a specific inhibitor of phosphatidylinositol-3-kinase, induces accumulation of DNA double-strand breaks.
Journal of radiation research 61, 171-176 [PubMed:32052028]
[show Abstract]

Cantrell W, Huang Y, Menchaca AA, Kulik G, Welker ME (2018)
Synthesis and PI3 Kinase Inhibition Activity of a Wortmannin-Leucine Derivative.
Molecules (Basel, Switzerland) 23, E1791 [PubMed:30036994]
[show Abstract]

Wang Y, Kuramitsu Y, Baron B, Kitagawa T, Tokuda K, Akada J, Maehara SI, Maehara Y, Nakamura K (2017)
PI3K inhibitor LY294002, as opposed to wortmannin, enhances AKT phosphorylation in gemcitabine-resistant pancreatic cancer cells.
International journal of oncology 50, 606-612 [PubMed:28000865]
[show Abstract]

Guo Y, Quan T, Lu Y, Luo T (2017)
Enantioselective Total Synthesis of (+)-Wortmannin.
Journal of the American Chemical Society 139, 6815-6818 [PubMed:28474885]
[show Abstract]

Foissner I, Sommer A, Hoeftberger M, Hoepflinger MC, Absolonova M (2016)
Is Wortmannin-Induced Reorganization of the trans-Golgi Network the Key to Explain Charasome Formation?
Frontiers in plant science 7, 756 [PubMed:27375631]
[show Abstract]

Li Y, Wang X, Wei Z, Mao H, Gao M, Liu Y, Ma Y, Liu X, Guo C, Zhang L, Wang X (2014)
Pretreatment with wortmannin alleviates lipopolysaccharide/d-galactosamine-induced acute liver injury.
Biochemical and biophysical research communications 455, 234-240 [PubMed:25449276]
[show Abstract]

Chatterjee S, Browning EA, Hong N, DeBolt K, Sorokina EM, Liu W, Birnbaum MJ, Fisher AB (2012)
Membrane depolarization is the trigger for PI3K/Akt activation and leads to the generation of ROS.
American journal of physiology. Heart and circulatory physiology 302, H105-14 [PubMed:22003059]
[show Abstract]

Kim SH, Jang YW, Hwang P, Kim HJ, Han GY, Kim CW (2012)
The reno-protective effect of a phosphoinositide 3-kinase inhibitor wortmannin on streptozotocin-induced proteinuric renal disease rats.
Experimental & molecular medicine 44, 45-51 [PubMed:22056625]
[show Abstract]

Takáč T, Pechan T, Samajová O, Ovečka M, Richter H, Eck C, Niehaus K, Samaj J (2012)
Wortmannin treatment induces changes in Arabidopsis root proteome and post-Golgi compartments.
Journal of proteome research 11, 3127-3142 [PubMed:22524784]
[show Abstract]

Moskalev AA, Shaposhnikov MV (2010)
Pharmacological inhibition of phosphoinositide 3 and TOR kinases improves survival of Drosophila melanogaster.
Rejuvenation research 13, 246-247 [PubMed:20017609]
[show Abstract]

Mandelker D, Gabelli SB, Schmidt-Kittler O, Zhu J, Cheong I, Huang CH, Kinzler KW, Vogelstein B, Amzel LM (2009)
A frequent kinase domain mutation that changes the interaction between PI3Kalpha and the membrane.
Proceedings of the National Academy of Sciences of the United States of America 106, 16996-17001 [PubMed:19805105]
[show Abstract]

Elling RA, Fucini RV, Romanowski MJ (2008)
Structures of the wild-type and activated catalytic domains of Brachydanio rerio Polo-like kinase 1 (Plk1): changes in the active-site conformation and interactions with ligands.
Acta crystallographica. Section D, Biological crystallography 64, 909-918 [PubMed:18703838]
[show Abstract]

Walker EH, Pacold ME, Perisic O, Stephens L, Hawkins PT, Wymann MP, Williams RL (2000)
Structural determinants of phosphoinositide 3-kinase inhibition by wortmannin, LY294002, quercetin, myricetin, and staurosporine.
Molecular cell 6, 909-919 [PubMed:11090628]
[show Abstract]

Last Modified

28 October 2021

CHEBI:52289 - wortmannin

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