(1S,12S,13R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol

• ChemBase ID: 154464
• Molecular Formular: C20H19NO5
• Molecular Mass: 353.36856
• Monoisotopic Mass: 353.12632271
• SMILES: CN1Cc2c(ccc3c2OCO3)[C@@H]2[C@H]1c1cc3c(cc1C[C@@H]2O)OCO3
• Canonical SMILES: CN1Cc2c([C@@H]3[C@H]1c1cc4OCOc4cc1C[C@@H]3O)ccc1c2OCO1
• InChI: InChI=1S/C20H19NO5/c1-21-7-13-11(2-3-15-20(13)26-9-23-15)18-14(22)4-10-5-16-17(25-8-24-16)6-12(10)19(18)21/h2-3,5-6,14,18-19,22H,4,7-9H2,1H3/t14-,18-,19+/m0/s1
• InChIKey: GHKISGDRQRSCII-ZOCIIQOWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,12S,13R)-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.0^2,^1^0.0^4,^8.0^1^4,^2^2.0^1^7,^2^1]tetracosa-2,4(8),9,14(22),15,17(21)-hexaen-12-ol
• IUPAC Traditional name: chelidonine
• Synonyms: Stylophorin; Chelidonine

Database IDs

• CAS Number: 476-32-4
• EC Number: 207-504-1
• MDL Number: MFCD00069660
• PubChem SID: 162248603
• PubChem CID: 197810

CALCULATED PROPERTIES

• Acid pKa: 14.643888
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.6219727
• LogD (pH = 7.4): 2.0454962
• Log P: 2.0547447
• Molar Refractivity: 93.0082 cm^3
• Polarizability: 36.442684 Å^3
• Polar Surface Area: 60.39 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: FL9450000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36/37
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (HPLC)
• Impurities: ~5% water
• Empirical Formula (Hill Notation): C20H19NO5

DETAILS

Sigma Aldrich - 54274

Biochem/physiol Actions
Inhibits tubulin polymerisation (IC50=24 μM), thereby disrupting microtubule structure in cells and inducing a G2/M mitotic arrest.