(1S,2R,5S,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0?,??.0?,??.0??,??.0??,??]tetracosa-9,16(24),17,19,21-pentaen-8-one

• ChemBase ID: 105754
• Molecular Formular: C27H33NO4
• Molecular Mass: 435.55522
• Monoisotopic Mass: 435.24095854
• SMILES: CC(C)([C@@H]1C(=O)C=C2[C@H](CC[C@]3(C)[C@]4(C)[C@@H](CC[C@@]23O)Cc2c3ccccc3[nH]c42)O1)O
• Canonical SMILES: O=C1C=C2[C@@H](O[C@@H]1C(O)(C)C)CC[C@]1([C@@]2(O)CC[C@@H]2[C@]1(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/t15-,21-,23-,25+,26+,27+/m0/s1
• InChIKey: ACNHBCIZLNNLRS-UBGQALKQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,7R,11S,14S)-11-hydroxy-7-(2-hydroxypropan-2-yl)-1,2-dimethyl-6-oxa-23-azahexacyclo[12.10.0.0?,??.0?,??.0??,??.0??,??]tetracosa-9,16(24),17,19,21-pentaen-8-one; (1S,2R,5S,7R,11S,14S)-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: paxilline
• Synonyms: PAXILLINE

Database IDs

• CAS Number: 57186-25-1
• PubChem SID: 162092801
• PubChem CID: 105008
• CHEMBL: 410063
• Chemspider ID: 94753
• MeSH Name: Paxilline
• Wikipedia Title: Paxilline

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

Safety Information

• Storage Condition: -20°C
• RTECS: DJ2830000

DETAILS

MP Biomedicals - 02193944

From Penicillium paxilli
This fungal mycotoxin possess potent excitatory action on acetylcholine release from nerve terminals. It specifically inhibits smooth muscle high conductance Ca^2+ -activated K^+ channels, as well as, enhances [^125 I]-charybotoxin binding to these channels.

REFERENCES

• Knaus, et al., Biochemistry , 33 : 5819 (1994).