3,13,23-triazahexacyclo[14.7.0.0^{2,10}.0^{4,9}.0^{11,15}.0^{17,22}]tricosa-1,4,6,8,10,15,17,19,21-nonaen-12-one

• ChemBase ID: 5664
• Molecular Formular: C20H13N3O
• Molecular Mass: 311.33672
• Monoisotopic Mass: 311.10586205
• SMILES: C1NC(=O)c2c1c1c([nH]c3c1cccc3)c1c2c2c([nH]1)cccc2
• Canonical SMILES: O=C1NCc2c1c1c([nH]c3c1cccc3)c1c2c2ccccc2[nH]1
• InChI: InChI=1S/C20H13N3O/c24-20-17-12(9-21-20)15-10-5-1-3-7-13(10)22-18(15)19-16(17)11-6-2-4-8-14(11)23-19/h1-8,22-23H,9H2,(H,21,24)
• InChIKey: MEXUTNIFSHFQRG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,13,23-triazahexacyclo[14.7.0.0^{2,10}.0^{4,9}.0^{11,15}.0^{17,22}]tricosa-1,4,6,8,10,15,17,19,21-nonaen-12-one; 3,13,23-triazahexacyclo[14.7.0.0^2,^1^0.0^4,^9.0^1^1,^1^5.0^1^7,^2^2]tricosa-1(16),2(10),4(9),5,7,11(15),17,19,21-nonaen-12-one
• IUPAC Traditional name: 3,13,23-triazahexacyclo[14.7.0.0^{2,10}.0^{4,9}.0^{11,15}.0^{17,22}]tricosa-1,4,6,8,10,15,17,19,21-nonaen-12-one; 3,13,23-triazahexacyclo[14.7.0.0^2,^1^0.0^4,^9.0^1^1,^1^5.0^1^7,^2^2]tricosa-1(16),2(10),4(9),5,7,11(15),17,19,21-nonaen-12-one
• Synonyms: 6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazol-5-one; K-252c; Staurosporine aglycone; Staurosporonine; K252c, Ready Made Solution; Staurosporine aglycone

Database IDs

• EC Number: 200-664-3
• MDL Number: MFCD00236435
• PubChem SID: 99444507; 160969091; 24899575
• PubChem CID: 3815

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.286813
• H Acceptors: 1
• H Donor: 3
• LogD (pH = 5.5): 3.034069
• LogD (pH = 7.4): 3.0340688
• Log P: 3.0340693
• Molar Refractivity: 93.4161 cm^3
• Polarizability: 39.961216 Å^3
• Polar Surface Area: 60.68 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.57
• LOG S: -4.77
• Solubility (Water): 5.28e-03 g/l

PROPERTIES

Physical Property

• Solubility: DMSO: soluble
• Apperance: crystalline powder

Safety Information

• German water hazard class: 1; 3
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US); Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... CDK2(1017)

Product Information

• Purity: >95% (HPLC); ≥95%
• Biological Source: from Streptomyces albus
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C20H13N3O

DETAILS

DrugBank - DB08036

Drug information: experimental

Sigma Aldrich - S3939

Biochem/physiol Actions
K-252c is a PKC inhibitor active at submicromolar concentrations.

Sigma Aldrich - K1890

Physical form
Supplied as a 1.6 mM, 0.2 μm-filtered solution in dimethyl sulfoxide (DMSO).
Biochem/physiol Actions
K252c belongs to the K252 family of compounds, which are general and potent inhibitors of various protein kinases.1 K252c is a protein kinase C inhibitor, weaker than K252b (IC50 of K252c = 214 nM and IC50 of K252b = 38.3 nM).1 K252c is also a weak inhibitor of calcium/calmodulin-activated phosphodiesterase with IC50 values of 297 μM for the brain enzyme.1, K252c expresses potent cytotoxicity against lung cancer A549 cells in vitro with an IC50 of 2.0 μM and against P388, IC50 = 3.2 μM.2, K252c exhibits moderate cytotoxic activity against K562 cells and induces apoptotic responses at 10 μM.3