(4Z)-4-(1-hydroxyethylidene)-6,7,7-trimethyl-6,15-diazatetracyclo[8.6.1.02,8.014,17]heptadeca-1(16),10,12,14(17)-tetraene-3,5-dione

• ChemBase ID: 133560
• Molecular Formular: C20H22N2O3
• Molecular Mass: 338.40028
• Monoisotopic Mass: 338.16304257
• SMILES: C/C(=C/1\C(=O)C2c3c[nH]c4c3c(ccc4)CC2C(N(C1=O)C)(C)C)/O
• Canonical SMILES: C/C(=C\1/C(=O)N(C)C(C2C(C1=O)c1c[nH]c3c1c(C2)ccc3)(C)C)/O
• InChI: InChI=1S/C20H22N2O3/c1-10(23)15-18(24)17-12-9-21-14-7-5-6-11(16(12)14)8-13(17)20(2,3)22(4)19(15)25/h5-7,9,13,17,21,23H,8H2,1-4H3/b15-10-
• InChIKey: WJCPGKDPOYBOOJ-GDNBJRDFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4Z)-4-(1-hydroxyethylidene)-6,7,7-trimethyl-6,15-diazatetracyclo[8.6.1.0^2,^8.0^1^4,^1^7]heptadeca-1(16),10,12,14(17)-tetraene-3,5-dione
• IUPAC Traditional name: (4Z)-4-(1-hydroxyethylidene)-6,7,7-trimethyl-6,15-diazatetracyclo[8.6.1.0^2,^8.0^1^4,^1^7]heptadeca-1(16),10,12,14(17)-tetraene-3,5-dione
• Synonyms: CPA; Cyclopiazonic acid from Penicillium cyclopium

Database IDs

• CAS Number: 18172-33-3
• MDL Number: MFCD00167445
• PubChem SID: 24892420; 162227837
• PubChem CID: 54695722

CALCULATED PROPERTIES

• Acid pKa: 4.170162
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.8308821
• LogD (pH = 7.4): -0.85347885
• Log P: 2.2419589
• Molar Refractivity: 97.1471 cm^3
• Polarizability: 37.82527 Å^3
• Polar Surface Area: 73.4 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: chloroform: soluble; DMSO: soluble
• Apperance: white to off-white powder

Safety Information

• RTECS: UY8587000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 25
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... ADORA1(134), ADORA2A(135), ADORA3(140)mouse ... Adora1(11539)rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - C1530

Biochem/physiol Actions
Inhibits the sarcoplasmic reticulum Ca2+-pump.