5-(1-hydroxyethylidene)-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0^{2,9}.0^{3,7}.0^{15,18}]octadeca-1(17),11(18),12,14-tetraene-4,6-dione

• ChemBase ID: 105133
• Molecular Formular: C20H20N2O3
• Molecular Mass: 336.3844
• Monoisotopic Mass: 336.14739251
• SMILES: C/C(=C\1/C(=O)C2C3C(Cc4c5c([nH]cc35)ccc4)C(C)(C)N2C1=O)/O
• Canonical SMILES: C/C(=C\1/C(=O)C2N(C1=O)C(C1C2c2c[nH]c3c2c(C1)ccc3)(C)C)/O
• InChI: InChI=1S/C20H20N2O3/c1-9(23)14-18(24)17-16-11-8-21-13-6-4-5-10(15(11)13)7-12(16)20(2,3)22(17)19(14)25/h4-6,8,12,16-17,21,23H,7H2,1-3H3
• InChIKey: CNZIQHGDUXRUJS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(1-hydroxyethylidene)-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0^{2,9}.0^{3,7}.0^{15,18}]octadeca-1(17),11(18),12,14-tetraene-4,6-dione
• IUPAC Traditional name: 5-(1-hydroxyethylidene)-8,8-dimethyl-7,16-diazapentacyclo[9.6.1.0^{2,9}.0^{3,7}.0^{15,18}]octadeca-1(17),11(18),12,14-tetraene-4,6-dione
• Synonyms: CYCLOPIAZONIC ACID

Database IDs

• CAS Number: 18172-33-3
• PubChem SID: 162093282
• PubChem CID: 54675761

CALCULATED PROPERTIES

• Acid pKa: 3.951955
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.57336426
• LogD (pH = 7.4): -1.044669
• Log P: 2.1560252
• Molar Refractivity: 94.8761 cm^3
• Polarizability: 37.095264 Å^3
• Polar Surface Area: 73.4 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: 0°C, Desiccate
• RTECS: UY8587000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• Hazard Class: 6.1
• Packing Group: II
• Australian Hazchem: 2XE
• Risk Statements: R:25
• Safety Statements: S:28-36/37/39-45-53
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154

Product Information

• Purity: 98%

DETAILS

MP Biomedicals - 02158895

From Penicillium species
Purity: 98%
Intracellular Ca^2+ release inducer. Inhibits endoplasmic reticulum Ca^2+ -ATPase. Highly selective for sarcoplasmic reticulum Ca^2+ -ATPase.

REFERENCES

• Demaurex, N., et al., J. Biol. Chem. , 267 : 2318 (1992).
• Goeger, D.E., et al., Biochem. Pharmacol. , 37 : 978 (1988).
• Seidler, N.W., et al., J. Biol. Chem. , 264 : 17816 (1989).