(2S,3R,4R,6S)-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-8,10,12,14(28),15(19),20(27),21,23,25-nonaen-16-one

• ChemBase ID: 134161
• Molecular Formular: C28H26N4O3
• Molecular Mass: 466.53104
• Monoisotopic Mass: 466.20049071
• SMILES: C[C@@]12[C@@H]([C@@H](C[C@H](O1)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3C(=O)NC1)NC)OC
• Canonical SMILES: CN[C@@H]1C[C@@H]2O[C@]([C@@H]1OC)(C)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3CNC1=O
• InChI: InChI=1S/C28H26N4O3/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/h4-11,17,20,26,29H,12-13H2,1-3H3,(H,30,33)/t17-,20+,26-,28+/m1/s1
• InChIKey: HKSZLNNOFSGOKW-WIFUGMKFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R,6S)-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-8,10,12,14(28),15(19),20(27),21,23,25-nonaen-16-one; (2S,3R,4R,6S)-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),9,11,14(28),15(19),20(27),21,23,25-nonaen-16-one
• IUPAC Traditional name: (2S,3R,4R,6S)-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-8,10,12,14(28),15(19),20(27),21,23,25-nonaen-16-one; (2S,3R,4R,6S)-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),9,11,14(28),15(19),20(27),21,23,25-nonaen-16-one
• Synonyms: Antibiotic AM-2282; Staurosporine from Streptomyces sp.

Database IDs

• CAS Number: 62996-74-1
• MDL Number: MFCD00077402
• Beilstein Number: 1060573
• PubChem SID: 24899603; 162228438; 24899680
• PubChem CID: 9937179

CALCULATED PROPERTIES

• Acid pKa: 14.562835
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.7899368
• LogD (pH = 7.4): 1.8470752
• Log P: 3.9696732
• Molar Refractivity: 132.3721 cm^3
• Polarizability: 55.985493 Å^3
• Polar Surface Area: 69.45 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; ethanol: soluble; H2O: insoluble; methanol: soluble
• Apperance: film

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-46
• Safety Statements: 53-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H340-H350
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPLC); ≥95.0% (HPLC)
• Grade: for molecular biology
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C28H26N4O3

DETAILS

Sigma Aldrich - S5921

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Analysis Note
Tested for inhibition of interleukin 2 production in Jurkat cells.
Biochem/physiol Actions
Potent inhibitor of phospholipid/calcium-dependent protein kinase. Inhibits the upregulation of VEGF expression in tumor cells.
Partially reverses MDR, sensitizing cells with MDR phenotype to cytotoxic agents. Inhibits Pgp phosphorylation. However, functional significance of Pgp phosphorylation is ill defined.

Sigma Aldrich - S4400

Biochem/physiol Actions
Potent inhibitor of phospholipid/calcium-dependent protein kinase. Inhibits the upregulation of VEGF expression in tumor cells.
Partially reverses MDR, sensitizing cells with MDR phenotype to cytotoxic agents. Inhibits Pgp phosphorylation. However, functional significance of Pgp phosphorylation is ill defined.

Sigma Aldrich - 85658

Biochem/physiol Actions
Potent inhibitor of phospholipid/calcium-dependent protein kinase. Inhibits the upregulation of VEGF expression in tumor cells.

Sigma Aldrich - 85660

Biochem/physiol Actions
Potent inhibitor of phospholipid/calcium-dependent protein kinase. Inhibits the upregulation of VEGF expression in tumor cells.
Other Notes
A potent inhibitor of phospholipid / calcium dependent protein kinase1,2; Inhibits the respiratory burst and induces exocytosis in human neutrophils3