11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.02,11.05,10.016,24.017,22]tetracosa-9,16(24),17,19,21-pentaen-8-one

• ChemBase ID: 132828
• Molecular Formular: C27H33NO4
• Molecular Mass: 435.55522
• Monoisotopic Mass: 435.24095854
• SMILES: CC12CCC3C(=CC(=O)C(O3)C(C)(C)O)C1(CCC1C2(c2c(c3ccccc3[nH]2)C1)C)O
• Canonical SMILES: O=C1C=C2C(OC1C(O)(C)C)CCC1(C2(O)CCC2C1(C)c1[nH]c3c(c1C2)cccc3)C
• InChI: InChI=1S/C27H33NO4/c1-24(2,30)23-20(29)14-18-21(32-23)10-11-25(3)26(4)15(9-12-27(18,25)31)13-17-16-7-5-6-8-19(16)28-22(17)26/h5-8,14-15,21,23,28,30-31H,9-13H2,1-4H3
• InChIKey: ACNHBCIZLNNLRS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0^2,^1^1.0^5,^1^0.0^1^6,^2^4.0^1^7,^2^2]tetracosa-9,16(24),17,19,21-pentaen-8-one
• IUPAC Traditional name: 11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0^2,^1^1.0^5,^1^0.0^1^6,^2^4.0^1^7,^2^2]tetracosa-9,16(24),17,19,21-pentaen-8-one
• Synonyms: Paxilline

Database IDs

• CAS Number: 57186-25-1
• MDL Number: MFCD00083464
• PubChem SID: 162227105; 24898374
• PubChem CID: 4697

CALCULATED PROPERTIES

• Acid pKa: 13.558903
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.6230834
• LogD (pH = 7.4): 3.6230829
• Log P: 3.6230834
• Molar Refractivity: 123.2165 cm^3
• Polarizability: 49.2091 Å^3
• Polar Surface Area: 82.55 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: faint yellow powder

Safety Information

• RTECS: DJ2830000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 23/24/25-36/37/38-41
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H318-H331-H335
• GHS Precautionary statements: P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (TLC)

DETAILS

Sigma Aldrich - P2928

Biochem/physiol Actions
Selective blocker of high-conductance Ca2+-activated (Maxi-K) potassium channels
Other Notes
Major toxin in Penicillium paxilli