methyl (15S,16R,18R)-16-hydroxy-15-methyl-3-oxo-28-oxa-4,14,19-triazaoctacyclo[12.11.2.115,18.02,6.07,27.08,13.019,26.020,25]octacosa-1(26),2(6),7(27),8,10,12,20(25),21,23-nonaene-16-carboxylate

• ChemBase ID: 154113
• Molecular Formular: C27H21N3O5
• Molecular Mass: 467.47274
• Monoisotopic Mass: 467.14812079
• SMILES: C[C@@]12[C@](C[C@H](O1)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3C(=O)NC1)(C(=O)OC)O
• Canonical SMILES: COC(=O)[C@@]1(O)C[C@@H]2O[C@]1(C)n1c3ccccc3c3c1c1n2c2ccccc2c1c1c3CNC1=O
• InChI: InChI=1S/C27H21N3O5/c1-26-27(33,25(32)34-2)11-18(35-26)29-16-9-5-3-7-13(16)20-21-15(12-28-24(21)31)19-14-8-4-6-10-17(14)30(26)23(19)22(20)29/h3-10,18,33H,11-12H2,1-2H3,(H,28,31)/t18?,26-,27-/m0/s1
• InChIKey: KOZFSFOOLUUIGY-BEJFKGIZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (15S,16R,18R)-16-hydroxy-15-methyl-3-oxo-28-oxa-4,14,19-triazaoctacyclo[12.11.2.1^1^5,^1^8.0^2,^6.0^7,^2^7.0^8,^1^3.0^1^9,^2^6.0^2^0,^2^5]octacosa-1(26),2(6),7(27),8,10,12,20(25),21,23-nonaene-16-carboxylate
• IUPAC Traditional name: methyl (15S,16R,18R)-16-hydroxy-15-methyl-3-oxo-28-oxa-4,14,19-triazaoctacyclo[12.11.2.1^1^5,^1^8.0^2,^6.0^7,^2^7.0^8,^1^3.0^1^9,^2^6.0^2^0,^2^5]octacosa-1(26),2(6),7(27),8,10,12,20(25),21,23-nonaene-16-carboxylate
• Synonyms: K-252a

Database IDs

• CAS Number: 99533-80-9
• EC Number: 200-664-3
• MDL Number: MFCD00161522
• PubChem SID: 24896210; 162248252
• PubChem CID: 3035817

CALCULATED PROPERTIES

• Acid pKa: 10.71429
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.4832048
• LogD (pH = 7.4): 3.4829972
• Log P: 3.4832075
• Molar Refractivity: 126.1198 cm^3
• Polarizability: 53.223053 Å^3
• Polar Surface Area: 94.72 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble1 mg/mL; DMSO: soluble1 mg/mL
• Flash Point: 188.6 °F; 87 °C

Safety Information

• RTECS: NZ0550000
• 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 ... NTRK1(4914)rat ... Prkca(24680)

Product Information

• Purity: >98%; ≥98% (HPLC)
• Biological Source: from Nonomuraea longicatena
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C27H21N3O5

DETAILS

Sigma Aldrich - K2015

Physical form
Supplied as a 0.2 μm-filtered 1 mM solution in dimethyl sulfoxide (DMSO).
Biochem/physiol Actions
K-252a is also a specific inhibitor of Trk (tyrosine kinase) receptors and selectively blocks the effect of nerve growth factor.1 At lower concentrations, K-252a acts as a neuroprotective compound prompting survival of primary neuronal cultures.2 K-252a induces cell cycle arrest and apoptosis by inhibiting both Cdc2 and Cdc25c.3 K-252a improves psoriasis in a SCID mouse-human skin model4 and also suppresses referred mechanical hypersensitivity and neuropeptide up-regulation associated with acute pancreatitis.5