(2S,3R,4R,6R)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.12,6.07,28.08,13.015,19.020,27.021,26]nonacosa-8(13),14(28),15(19),20(27),21(26),22,24-heptaen-16-one

• ChemBase ID: 178417
• Molecular Formular: C28H30N4O3
• Molecular Mass: 470.5628
• Monoisotopic Mass: 470.23179084
• SMILES: c12c3c4c(c5c1n(c1c5CCCC1)[C@H]1C[C@H]([C@H]([C@@](n2c2c3cccc2)(O1)C)OC)NC)C(=O)NC4
• Canonical SMILES: CN[C@@H]1C[C@H]2O[C@]([C@@H]1OC)(C)n1c3ccccc3c3c1c1n2c2CCCCc2c1c1c3CNC1=O
• InChI: InChI=1S/C28H30N4O3/c1-28-26(34-3)17(29-2)12-20(35-28)31-18-10-6-4-8-14(18)22-23-16(13-30-27(23)33)21-15-9-5-7-11-19(15)32(28)25(21)24(22)31/h5,7,9,11,17,20,26,29H,4,6,8,10,12-13H2,1-3H3,(H,30,33)/t17-,20?,26-,28+/m1/s1
• InChIKey: KIZWKTROWIIMNN-ZGQXJOJZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R,6R)-3-methoxy-2-methyl-4-(methylamino)-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(13),14(28),15(19),20(27),21(26),22,24-heptaen-16-one
• IUPAC Traditional name: (2S,3R,4R,6R)-3-methoxy-2-methyl-4-(methylamino)-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(13),14(28),15(19),20(27),21(26),22,24-heptaen-16-one
• Synonyms: (9S,10R,11R,13R)-2,3,10,11,12,13,15,16,17,18-Decahydro-10-methoxy-9-methyl-11-(methylamino)-9,13-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-lm]pyrrolo[3,4-j][1,7]benzodiazonin-1-one; AFN 941; 1,2,3,4-Tetrahydro Staurosporine

Database IDs

• CAS Number: 220038-19-7
• PubChem SID: 164234327
• PubChem CID: 4369398

CALCULATED PROPERTIES

• Acid pKa: 14.130311
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.987406
• LogD (pH = 7.4): 2.0445402
• Log P: 4.1671433
• Molar Refractivity: 133.5581 cm^3
• Polarizability: 54.890465 Å^3
• Polar Surface Area: 69.45 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: >230°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T295700

Staurosporine derivative for use as isoenzyme PKCα inhibitors and anticancer agents.

REFERENCES

• Pollack, V., et al.: J. Pharmacol. Exp. Ther., 291, 739 (1999)
• Barker, A., et al.: Bioorg. Med. Chem. Lett., 11, 1911 (1999)
• Brignola, P., et al.: J. Biol. Chem., 277, 1576 (1999)
• Amann, J., et al.: Cancer Res., 65, 226 (1999)
• Zhang, X., et al.: Cell,