N-[(2R,4R,5R,6S)-5-methoxy-6-methyl-18-oxo-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 hydrate

• ChemBase ID: 154378
• Molecular Formular: C35H32N4O5
• Molecular Mass: 588.65238
• Monoisotopic Mass: 588.23727014
• SMILES: C[C@@]12[C@@H]([C@@H](C[C@@H](O1)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3C(=O)NC1)N(C)C(=O)c1ccccc1)OC.O
• Canonical SMILES: CO[C@@H]1[C@@H](C[C@H]2O[C@]1(C)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3CNC1=O)N(C(=O)c1ccccc1)C.O
• InChI: InChI=1S/C35H30N4O4.H2O/c1-35-32(42-3)25(37(2)34(41)19-11-5-4-6-12-19)17-26(43-35)38-23-15-9-7-13-20(23)28-29-22(18-36-33(29)40)27-21-14-8-10-16-24(21)39(35)31(27)30(28)38;/h4-16,25-26,32H,17-18H2,1-3H3,(H,36,40);1H2/t25-,26-,32-,35+;/m1./s1
• InChIKey: YEKDLUZCCDJYAJ-LJAYRLSQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,4R,5R,6S)-5-methoxy-6-methyl-18-oxo-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 hydrate
• IUPAC Traditional name: N-[(2R,4R,5R,6S)-5-methoxy-6-methyl-18-oxo-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 hydrate
• Synonyms: CGP 41251; N-[(9S,10R,11R,13R)-2,3,10,11,12,13-Hexahydro-10-methoxy-9-methyl-1-oxo-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-benzoylstaurosporine; PKC-412; Midostaurin hydrate

Database IDs

• MDL Number: MFCD12828879
• PubChem SID: 162248517
• PubChem CID: 71311854

CALCULATED PROPERTIES

• Acid pKa: 14.56283
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 5.4337883
• LogD (pH = 7.4): 5.4337897
• Log P: 5.4337897
• Molar Refractivity: 162.6085 cm^3
• Polarizability: 66.85327 Å^3
• Polar Surface Area: 77.73 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL
• Apperance: off-white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C35H30N4O4 · xH2O

DETAILS

Sigma Aldrich - M1323

Biochem/physiol Actions
Midostaurin is an inhibitor of tyrosine kinase, protein kinase C, and VEGF. Midostaurin inhibits cell growth and phosphorylation of FLT3, STAT5, and ERK. It is a potent inhibitor of a spectrum of FLT3 activation loop mutations.