3,6-dimethyl-9-[6-(oxiran-2-yl)-6-oxohexyl]-tetradecahydropyrrolo[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone

• ChemBase ID: 132714
• Molecular Formular: C21H32N4O6
• Molecular Mass: 436.50198
• Monoisotopic Mass: 436.23218476
• SMILES: CC1C(=O)NC(C(=O)N2CCCC2C(=O)NC(C(=O)N1)C)CCCCCC(=O)C1CO1
• Canonical SMILES: O=C1NC(CCCCCC(=O)C2CO2)C(=O)N2CCCC2C(=O)NC(C(=O)NC1C)C
• InChI: InChI=1S/C21H32N4O6/c1-12-18(27)22-13(2)19(28)24-14(7-4-3-5-9-16(26)17-11-31-17)21(30)25-10-6-8-15(25)20(29)23-12/h12-15,17H,3-11H2,1-2H3,(H,22,27)(H,23,29)(H,24,28)
• InChIKey: GNYCTMYOHGBSBI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,6-dimethyl-9-[6-(oxiran-2-yl)-6-oxohexyl]-tetradecahydropyrrolo[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone
• IUPAC Traditional name: 3,6-dimethyl-9-[6-(oxiran-2-yl)-6-oxohexyl]-decahydropyrrolo[1,2-a]1,4,7,10-tetraazacyclododecane-1,4,7,10-tetrone
• Synonyms: HC toxin from Helminthosporium carbonum

Database IDs

• CAS Number: 83209-65-8
• MDL Number: MFCD00133388
• PubChem SID: 24895790; 162226991
• PubChem CID: 3571

CALCULATED PROPERTIES

• Acid pKa: 10.796976
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -0.69692177
• LogD (pH = 7.4): -0.69707406
• Log P: -0.6969198
• Molar Refractivity: 109.2529 cm^3
• Polarizability: 42.978123 Å^3
• Polar Surface Area: 137.21 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: lyophilized powder

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 90-95% (TLC)

DETAILS

Sigma Aldrich - H7270

Biochem/physiol Actions
Cyclic tetrapeptide1 fungal toxin selectively toxic to plants with susceptible host genotype.2