N-[(2S,4R,5R,6S)-5-methoxy-6-methyl-16,18-dioxo-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8,10,12,14(28),15(19),20(27),21(26),22,24-nonaen-4-yl]-N-methylbenzamide

• ChemBase ID: 154314
• Molecular Formular: C35H28N4O5
• Molecular Mass: 584.62062
• Monoisotopic Mass: 584.20597002
• SMILES: C[C@@]12[C@@H]([C@@H](C[C@H](O1)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3c(=O)[nH]c1=O)N(C)C(=O)c1ccccc1)OC
• Canonical SMILES: CO[C@@H]1[C@@H](C[C@@H]2O[C@]1(C)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3c(=O)[nH]c1=O)N(C(=O)c1ccccc1)C
• InChI: InChI=1S/C35H28N4O5/c1-35-31(43-3)23(37(2)34(42)18-11-5-4-6-12-18)17-24(44-35)38-21-15-9-7-13-19(21)25-27-28(33(41)36-32(27)40)26-20-14-8-10-16-22(20)39(35)30(26)29(25)38/h4-16,23-24,31H,17H2,1-3H3,(H,36,40,41)/t23-,24+,31-,35+/m1/s1
• InChIKey: MQCCJEYZKWZQHU-JTPSWESPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,4R,5R,6S)-5-methoxy-6-methyl-16,18-dioxo-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1^2,^6.0^7,^2^8.0^8,^1^3.0^1^5,^1^9.0^2^0,^2^7.0^2^1,^2^6]nonacosa-8,10,12,14(28),15(19),20(27),21(26),22,24-nonaen-4-yl]-N-methylbenzamide
• IUPAC Traditional name: N-[(2S,4R,5R,6S)-5-methoxy-6-methyl-16,18-dioxo-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1^2,^6.0^7,^2^8.0^8,^1^3.0^1^5,^1^9.0^2^0,^2^7.0^2^1,^2^6]nonacosa-8,10,12,14(28),15(19),20(27),21(26),22,24-nonaen-4-yl]-N-methylbenzamide
• Synonyms: Stauprimide

Database IDs

• CAS Number: 154589-96-5
• PubChem SID: 162248453
• PubChem CID: 71311840

CALCULATED PROPERTIES

• Acid pKa: 8.031408
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 5.3271093
• LogD (pH = 7.4): 5.238331
• Log P: 5.3284235
• Molar Refractivity: 163.3356 cm^3
• Polarizability: 66.67411 Å^3
• Polar Surface Area: 94.8 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >20 mg/mL
• Apperance: white to off-white powder

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C35H28N4O5

DETAILS

Sigma Aldrich - S2951

Biochem/physiol Actions
Stauprimide is an enhancer stem cell differentiation into endoderm. In vitro differentiation of embryonic stem cells is of great interest to regenerative medicine, and current protocols are labor-intensive and expensive. Small molecules that induce or enhance differentiation are highly desired. High-content screening identified compounds that enhance endodermal differentiation in the presence of low levels of Activin A. Stauprimide increased definitive endodermal markers but not markers for visceral/parietal endoderm or mesoderm. Stauprimide-differentiated cells could be further differentiated into hepatocytes. Stauprimide treatment during differentiation decreased the concentration of Activin A required for definitive endoderm formation, and it eliminated the need for serum. The mechanism of action of stauprimide is to sensitize cells for differentiation. Stauprimide enabled differentiation into other cell lineages under varying differentiation conditions, including neurons, hematopoietic mesoderm, beating cardiac myocytes, and skeletal muscle. The cellular target of stauprimide was determined to be inhibition of NME2 transcription factor translocation to the nucleus, leading to down-regulation of c-Myc expression.