(2S,3R,4R,6R,18S)-18-hydroxy-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),9,11,14(28),15(19),20(27),21,23,25-nonaen-16-one

• ChemBase ID: 155451
• Molecular Formular: C28H26N4O4
• Molecular Mass: 482.53044
• Monoisotopic Mass: 482.19540533
• SMILES: C[C@@]12[C@@H]([C@@H](C[C@@H](O1)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3C(=O)N[C@H]1O)NC)OC
• Canonical SMILES: CN[C@@H]1C[C@H]2O[C@]([C@@H]1OC)(C)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3[C@@H](NC1=O)O
• InChI: InChI=1S/C28H26N4O4/c1-28-25(35-3)15(29-2)12-18(36-28)31-16-10-6-4-8-13(16)19-21-22(27(34)30-26(21)33)20-14-9-5-7-11-17(14)32(28)24(20)23(19)31/h4-11,15,18,25,27,29,34H,12H2,1-3H3,(H,30,33)/t15-,18-,25-,27+,28+/m1/s1
• InChIKey: PBCZSGKMGDDXIJ-KRUBCLEUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R,6R,18S)-18-hydroxy-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,6R,18S)-18-hydroxy-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: KW-2401; UCN-01

Database IDs

• CAS Number: 112953-11-4
• PubChem SID: 162249589; 24724639
• PubChem CID: 3078519

CALCULATED PROPERTIES

• Acid pKa: 12.815151
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 0.42571327
• LogD (pH = 7.4): 1.4828526
• Log P: 3.6054492
• Molar Refractivity: 133.402 cm^3
• Polarizability: 56.554142 Å^3
• Polar Surface Area: 89.68 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >5 mg/mL; H2O: insoluble
• Apperance: light yellow powder

Safety Information

• Storage Condition: protect from light
• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C28H26N4O4

DETAILS

Sigma Aldrich - U6508

Biochem/physiol Actions
UCN-01 is a selective inhibitor for conventional PKC isotypes over novel PKC isotypes.