(2S,3R,4R,6R)-4-{[(2H5)benzyl](methyl)amino}-3-methoxy-2-methyl-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-nonaene-16,18-dione

• ChemBase ID: 177859
• Molecular Formular: C35H30N4O4
• Molecular Mass: 570.6371
• Monoisotopic Mass: 570.22670546
• SMILES: c12c3c4c(c5c1n(c1c5cccc1)[C@H]1C[C@H]([C@H]([C@@](n2c2c3cccc2)(O1)C)OC)N(C)Cc1ccccc1)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(Cc1ccccc1)C
• InChI: InChI=1S/C35H30N4O4/c1-35-32(42-3)24(37(2)18-19-11-5-4-6-12-19)17-25(43-35)38-22-15-9-7-13-20(22)26-28-29(34(41)36-33(28)40)27-21-14-8-10-16-23(21)39(35)31(27)30(26)38/h4-16,24-25,32H,17-18H2,1-3H3,(H,36,40,41)/t24-,25?,32-,35+/m1/s1
• InChIKey: BGCHZMHNMQOZGG-HBXKOPBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R,6R)-4-{[(^2H₅)benzyl](methyl)amino}-3-methoxy-2-methyl-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-nonaene-16,18-dione
• IUPAC Traditional name: (2S,3R,4R,6R)-4-{[(^2H₅)benzyl](methyl)amino}-3-methoxy-2-methyl-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-nonaene-16,18-dione
• 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-d5; N-(Benzoyl-d5)-7-oxostaurosporine; Stauprimide-d5

Database IDs

• PubChem SID: 164233769
• PubChem CID: 71752235

CALCULATED PROPERTIES

• Acid pKa: 7.9803486
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.8126655
• LogD (pH = 7.4): 4.3538566
• Log P: 4.724174
• Molar Refractivity: 163.0065 cm^3
• Polarizability: 67.2933 Å^3
• Polar Surface Area: 77.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S684702

Labelled Stauprimide (S684700). It is an enhancer stem cell differentiation into endoderm.

REFERENCES

• Ji, L., et al.: J. Biol. Chem., 270, 13392 (1995)
• D'Amour, K., et al.: Nat. Biotechnol., 23, 1534 (1995)
• Eastham, A., et al.: Cancer Res., 67, 11254 (1995)