NAV

Wortmannin

Identification

Generic Name
Wortmannin
DrugBank Accession Number
DB08059
Background

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).

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 428.4319
Monoisotopic: 428.147117744
Chemical Formula
C23H24O8
Synonyms
  • Wartmannin
External IDs
  • NSC-627609
  • SL-2052
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoformNot AvailableHumans
USerine/threonine-protein kinase PLK1Not AvailableHumans
UPhosphatidylinositol 3-kinase regulatory subunit alphaNot AvailableHumans
UPhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoformNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Wortmannin is combined with 1,2-Benzodiazepine.
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Wortmannin.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with Wortmannin.
AcetazolamideThe risk or severity of CNS depression can be increased when Acetazolamide is combined with Wortmannin.
AcetophenazineThe risk or severity of CNS depression can be increased when Acetophenazine is combined with Wortmannin.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as oxasteroids and derivatives. These are steroid derivatives where a carbon atom of the steroid is replaced by an oxygen atom.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Oxasteroids and derivatives
Direct Parent
Oxasteroids and derivatives
Alternative Parents
Naphthopyrans / Naphthofurans / Naphthalenes / Furopyrans / Furoic acid esters / Aryl ketones / Pyrans / Dicarboxylic acids and derivatives / Heteroaromatic compounds / Lactones
show 5 more
Substituents
2-oxasteroid / Aromatic heteropolycyclic compound / Aryl ketone / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dialkyl ether / Dicarboxylic acid or derivatives / Ether / Furan
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cyclic ketone, organic heteropentacyclic compound, acetate ester, delta-lactone (CHEBI:52289)
Affected organisms
Not Available

Chemical Identifiers

UNII
XVA4O219QW
CAS number
19545-26-7
InChI Key
QDLHCMPXEPAAMD-QAIWCSMKSA-N
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
IUPAC Name
(1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.0^{2,10}.0^{5,9}.0^{15,19}]nonadeca-2(10),12(19),14-trien-3-yl acetate
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

References

General References
Not Available
KEGG Compound
C15181
PubChem Compound
312145
PubChem Substance
99444530
ChemSpider
276037
BindingDB
15234
ChEBI
52289
ChEMBL
CHEMBL428496
ZINC
ZINC000001619592
PDBe Ligand
KWT
Wikipedia
Wortmannin
PDB Entries
1e7u / 3d5x / 3hhm / 7otv

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.121 mg/mLALOGPS
logP2.31ALOGPS
logP1.44Chemaxon
logS-3.6ALOGPS
pKa (Strongest Basic)-3.2Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area109.11 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity106.86 m3·mol-1Chemaxon
Polarizability42.98 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9855
Blood Brain Barrier+0.957
Caco-2 permeable+0.5179
P-glycoprotein substrateSubstrate0.8161
P-glycoprotein inhibitor IInhibitor0.9581
P-glycoprotein inhibitor IIInhibitor0.9541
Renal organic cation transporterNon-inhibitor0.6551
CYP450 2C9 substrateNon-substrate0.8704
CYP450 2D6 substrateNon-substrate0.8509
CYP450 3A4 substrateSubstrate0.7654
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.5766
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7681
Ames testNon AMES toxic0.8847
CarcinogenicityNon-carcinogens0.9526
BiodegradationNot ready biodegradable0.9236
Rat acute toxicity4.0908 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8355
hERG inhibition (predictor II)Non-inhibitor0.6581
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a70-0009500000-d35038d955cb4044b624
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0000900000-9b163eab286155d21f8d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00n0-0019200000-ea7a4c3f9394845e695a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004j-2009100000-6e648ed9573213b7c004
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kp1-0009100000-59ea6d045203f838ed77
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kdi-2009200000-4cbe94841f184bff6588
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-207.1836247
predicted
DarkChem Lite v0.1.0
[M-H]-196.51462
predicted
DeepCCS 1.0 (2019)
[M+H]+208.1358247
predicted
DarkChem Lite v0.1.0
[M+H]+198.41002
predicted
DeepCCS 1.0 (2019)
[M+Na]+204.07713
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activity
Specific Function
Phosphoinositide-3-kinase (PI3K) that phosphorylates PtdIns(4,5)P2 (Phosphatidylinositol 4,5-bisphosphate) to generate phosphatidylinositol 3,4,5-trisphosphate (PIP3). PIP3 plays a key role by recr...
Gene Name
PIK3CG
Uniprot ID
P48736
Uniprot Name
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform
Molecular Weight
126452.625 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details2. Serine/threonine-protein kinase PLK1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activity
Specific Function
Serine/threonine-protein kinase that performs several important functions throughout M phase of the cell cycle, including the regulation of centrosome maturation and spindle assembly, the removal o...
Gene Name
PLK1
Uniprot ID
P53350
Uniprot Name
Serine/threonine-protein kinase PLK1
Molecular Weight
68254.03 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details3. Phosphatidylinositol 3-kinase regulatory subunit alpha
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transmembrane receptor protein tyrosine kinase adaptor activity
Specific Function
Binds to activated (phosphorylated) protein-Tyr kinases, through its SH2 domain, and acts as an adapter, mediating the association of the p110 catalytic unit to the plasma membrane. Necessary for t...
Gene Name
PIK3R1
Uniprot ID
P27986
Uniprot Name
Phosphatidylinositol 3-kinase regulatory subunit alpha
Molecular Weight
83597.675 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details4. Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein serine/threonine kinase activity
Specific Function
Phosphoinositide-3-kinase (PI3K) that phosphorylates PtdIns (Phosphatidylinositol), PtdIns4P (Phosphatidylinositol 4-phosphate) and PtdIns(4,5)P2 (Phosphatidylinositol 4,5-bisphosphate) to generate...
Gene Name
PIK3CA
Uniprot ID
P42336
Uniprot Name
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
Molecular Weight
124283.025 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:28 / Updated at June 30, 2022 20:57