(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

• ChemBase ID: 5687
• Molecular Formular: C23H24O8
• Molecular Mass: 428.43186
• Monoisotopic Mass: 428.14711773
• SMILES: [C@@H]1(OC(=O)c2c3[C@]1(C1=C(C(=O)c3oc2)[C@H]2[C@@](C[C@H]1OC(=O)C)(C)C(=O)CC2)C)COC
• Canonical SMILES: COC[C@H]1OC(=O)c2c3[C@@]1(C)C1=C(C(=O)c3oc2)[C@H]2[C@@](C[C@H]1OC(=O)C)(C)C(=O)CC2
• 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

NAMES AND DATABASE IDS

Names

• 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; (1R,3R,5S,9R,18S)-18-(methoxymethyl)-1,5-dimethyl-6,11,16-trioxo-13,17-dioxapentacyclo[10.6.1.0^2,^1^0.0^5,^9.0^1^5,^1^9]nonadeca-2(10),12(19),14-trien-3-yl acetate
• IUPAC Traditional name: wortmannin
• Synonyms: (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][2]BENZOPYRAN-11-YL ACETATE; Wortmannin; KY 12420; Wortmannin

Database IDs

• CAS Number: 19545-26-7
• MDL Number: MFCD00133927
• Beilstein Number: 67676
• PubChem SID: 160969114; 24278777; 99444530
• PubChem CID: 312145
• CHEMBL: 428496
• Chemspider ID: 276037
• Wikipedia Title: Wortmannin

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.667614
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 1.4426177
• LogD (pH = 7.4): 1.4426177
• Log P: 1.4426177
• Molar Refractivity: 106.8572 cm^3
• Polarizability: 41.506565 Å^3
• Polar Surface Area: 109.11 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.31
• LOG S: -3.55
• Solubility (Water): 1.21e-01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; H2O: unstable
• Apperance: off-white powder
• Melting Point: 238-242 °C

Safety Information

• RTECS: CB9641000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 26/27/28
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 1
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: PI3K
• Gene Information: human ... PIK3CD(5293), PIK3CG(5294), PIK3R1(5295)

Product Information

• Purity: ≥98% (HPLC and TLC); ≥98.0% (TLC)
• Salt Data: Free Base
• Biological Source: from Penicillium funiculosum
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C23H24O8

DETAILS

DrugBank - DB08059

Drug information: experimental

Sigma Aldrich - W1628

Biochem/physiol Actions
Wortmannin is a potent and specific phosphatidylinositol 3-kinase (PI3-K) inhibitor with an IC50 of 2-4 nM. Inhibition of PI3-K/Akt signal transduction cascade enhances the apoptotic effects of radiation or serum withdrawal and blocks the antiapoptotic effect of cytokines. Inhibition of PI3-K by wortmannin also blocks many of the short-term metabolic effects induced by insulin receptor activation.

Sigma Aldrich - 95455

Biochem/physiol Actions
Wortmannin is a potent and specific phosphatidylinositol 3-kinase (PI3-K) inhibitor with an IC50 of 2-4 nM. Inhibition of PI3-K/Akt signal transduction cascade enhances the apoptotic effects of radiation or serum withdrawal and blocks the antiapoptotic effect of cytokines. Inhibition of PI3-K by wortmannin also blocks many of the short-term metabolic effects induced by insulin receptor activation.