Basic information
- CAS
601514-19-6- Standard SMILES
Nc1cccc(-c2cc3c(Oc4cccc(O)c4)ncnc3[nH]2)c1- InChIKey
VPVLEBIVXZSOMQ-UHFFFAOYSA-N- Molecular formula
- C18H14N4O2
- Average molar mass
- 318.3 g/mol
- Monoisotopic mass
- 318.11167569
Overview
3-[[6-(3-aminophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenol is a member of pyrroles.
Names & identifiers
- Preferred name
- Tws119
- IUPAC
- 3-[[6-(3-aminophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenol
- English name
- GSK-3BETA INHIBITOR XII
- Molecular formula
- C18H14N4O2
- Molecular weight
- 318.33
Names & synonyms
TWS119601514-19-6TWS-1193-[[6-(3-Aminophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]phenolTWS 1193-{[6-(3-aminophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy}phenol3-((6-(3-AMINOPHENYL)-7H-PYRROLO[2,3-D]PYRIMIDIN-4-YL)OXY)PHENOLDTXSID004295503-((6-(3-aminophenyl)-7H-pyrrolo(2,3-d)pyrimidin-4-yl)oxy)phenolRefChem:192612DTXCID90380383GSK inhibitor XII
Show more names
TWS11TWS SCS-445CS-1924TWS119, >=98%OTAVA-BB 7070707013TWS119, 10 mM in DMSOGSK-3BETA INHIBITOR XII
MFCD090375353-(6-(3-aminophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenolCHEMBL405759GTPL5980SCHEMBL5559045CHEBI:91384EX-A151K00245
Database identifiers
- CAS
601514-19-6- PubChem CID
Properties
Computed structural properties
- XLogP
- 3.2
- Topological polar surface area
- 97.1 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 3
- Heavy atoms
- 24
- Formal charge
- 0
- Complexity
- 424
Physicochemical properties
- Melting point
- 249 °C · 249 °C
- Density
- 1.42 · 1.42
- storage temp.
- 2 · 2-8°C
- solubility
- 2 O; · insoluble in H2O; insoluble in EtOH; ≥15.9 mg/mL in DMSO
- pka
- 8.99 · 8.99±0.10(Predicted)
- form
- powder
- color
- white to beige
- InChI
- 1S/C18H14N4O2/c19-12-4-1-3-11(7-12)16-9-15-17(22-16)20-10-21-18(15)24-14-6-2-5-13(23)8-14/h1-10,23H,19H2,(H,20,21,22)
- InChIKey
- VPVLEBIVXZSOMQ-UHFFFAOYSA-N
- SMILES
- OC1=CC(OC2=NC=NC3=C2C=C(C4=CC=CC(N)=C4)N3)=CC=C1
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H319
- Precautionary statements
- 305 · P305+P351+P338
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (97.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (97.4%)
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H319
- Precautionary statements
- P305+P351+P338
Chemistry & industry
Applications
UsesTWS119 has been used as glycogen synthase kinase-3β (GSK-3β) GSK3β inhibitor.
UsesActs as an ARMS-selective inihibitor, through GSK3 (Glucose Synthase Kinase 3) inhibition.
General DescriptionA cell-permeable and potent inhibitor of GSK-3β (IC50 = 30 nM). Binds to GSK-3β with high-affinity (Kd = 126 nM), leading to an increase in the level of β-catenin, a downstream substrate of GSK-3β in the Wnt signaling pathway. Shown to selectively induce neuronal differentiation in both pluripotent murine embryonal carcinoma cells (P19; 30-40% at 1 μM) and embryonic stem cells (D3; 50-60% at 400 nM).
Upstream & downstream products
Upstream raw materials
Suppliers100 total
阿诺西（上海）生物技术有限公司400-1107768 15058188853 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
上海麦克林生化科技股份有限公司
Related reactions
1 records
Compound notes
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