N-[(2S,3R,4R,6R)-3-methoxy-2-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: 177858
• Molecular Formular: C35H28N4O5
• Molecular Mass: 584.62062
• Monoisotopic Mass: 584.20597002
• SMILES: c12c3c4c(c5c1n(c1c5cccc1)[C@H]1C[C@H]([C@H]([C@@](n2c2c3cccc2)(O1)C)OC)N(C)C(=O)c1ccccc1)c(=O)[nH]c4=O
• 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-UNFVMDDZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,6R)-3-methoxy-2-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: stauprimide
• Synonyms: N-[(9S,10R,11R,13R)-2,3,10,11,12,13-Hexahydro-10-methoxy-9-methyl-1,3-dioxo-9,13-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-11-yl]-N-methylbenzamide; N-Benzoyl-7-oxostaurosporine; Stauprimide

Database IDs

• CAS Number: 154589-96-5
• PubChem SID: 164233768
• PubChem CID: 46245328

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 (20mg/mL); only slightly soluble in EtOH

DETAILS

Toronto Research Chemicals - S684700

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 enh

REFERENCES

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• D'Amour, K., et al.: Nat. Biotechnol., 23, 1534 (1995)
• Eastham, A., et al.: Cancer Res., 67, 11254 (1995)
• S. Zhu et al.: Cell Stem Cell 4, 416 (1995)
• K.S. Zaret: Cell Stem Cell 4, 373 (2009)