N-(6-methyl-1,3-benzothiazol-2-yl)-2-({4-oxo-3-phenyl-3H,4H,6H,7H-thieno[3,2-d]pyrimidin-2-yl}sulfanyl)acetamide

• ChemBase ID: 154356
• Molecular Formular: C22H18N4O2S3
• Molecular Mass: 466.59892
• Monoisotopic Mass: 466.05918884
• SMILES: Cc1ccc2c(c1)sc(n2)NC(=O)CSc1nc2c(c(=O)n1c1ccccc1)SCC2
• Canonical SMILES: O=C(Nc1nc2c(s1)cc(cc2)C)CSc1nc2CCSc2c(=O)n1c1ccccc1
• InChI: InChI=1S/C22H18N4O2S3/c1-13-7-8-15-17(11-13)31-21(23-15)25-18(27)12-30-22-24-16-9-10-29-19(16)20(28)26(22)14-5-3-2-4-6-14/h2-8,11H,9-10,12H2,1H3,(H,23,25,27)
• InChIKey: WRKPZSMRWPJJDH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(6-methyl-1,3-benzothiazol-2-yl)-2-({4-oxo-3-phenyl-3H,4H,6H,7H-thieno[3,2-d]pyrimidin-2-yl}sulfanyl)acetamide
• IUPAC Traditional name: N-(6-methyl-1,3-benzothiazol-2-yl)-2-({4-oxo-3-phenyl-6H,7H-thieno[3,2-d]pyrimidin-2-yl}sulfanyl)acetamide
• Synonyms: N-(6-Methyl-2-benzothiazolyl)-2-[(3,4,6,7-tetrahydro-4-oxo-3-phenylthieno[3,2-d]pyrimidin-2-yl)thio]-acetamide; IWP-2; N-(6-Methyl-2-benzothiazolyl)-2-[(3,4,6,7-tetrahydro-4-oxo-3-phenylthieno[3,2-d]pyrimidin-2-yl)thio]acetamide; IWP-2

Database IDs

• CAS Number: 686770-61-6
• MDL Number: MFCD04457599
• PubChem SID: 162248495
• PubChem CID: 2155128

CALCULATED PROPERTIES

• Acid pKa: 10.617733
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.968937
• LogD (pH = 7.4): 4.968691
• Log P: 4.9689407
• Molar Refractivity: 128.7995 cm^3
• Polarizability: 49.32451 Å^3
• Polar Surface Area: 74.66 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL
• Apperance: powder

Safety Information

• Storage Condition: desiccated
• German water hazard class: 2
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H18N4O2S3

DETAILS

Sigma Aldrich - I0536

Biochem/physiol Actions
IWP-2 is an inactivator of Porcn function; inhibitor of Wnt production. Wnt/b-catenin (‘canonical’) pathway maintains transcriptional programs that enable stem cells to remain multipotent. Hyperactivation of the Wnt/b-catenin pathway leads to disease stage. IWP-2 inhibits Wnt production. It appears that IWP inactivates Porcn function either by directly inhibiting the Porcn active site or by modulating the function of a Porcn regulator. Porcn is a member of the membrane-bound O-acyltransferase (MBOAT) family, which adds a palmitoyl group to Wnt proteins that is essential to their signaling ability and is required for Wnt secretion. IWP-2 is useful in both regenerative medicine and anticancer efforts.

Toronto Research Chemicals - I941600

IWP-2 is an inactivator of Porcn function; inhibitor of Wnt production. IWP-2 is useful in the treatment diseases and conditions such as cancer, degenerative diseases, type II diabetes and osteopetrosis.

REFERENCES

• Poss, K., et al.: Dev. Biol., 222, 347 (2000)
• Tanaka, K., et al.: Eur. J. Biochem., 267, 4300 (2000)
• Clevers, H., et al.: Cell, 2006, 127, 469 (2000)