1-{6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl}-3-phenylprop-2-en-1-one

• ChemBase ID: 109393
• Molecular Formular: C30H28O8
• Molecular Mass: 516.53852
• Monoisotopic Mass: 516.17841786
• SMILES: CC(=O)c1c(O)c(Cc2c(O)c3c(OC(C)(C)C=C3)c(c2O)C(=O)/C=C/c2ccccc2)c(O)c(C)c1O
• Canonical SMILES: O=C(c1c(O)c(Cc2c(O)c(C)c(c(c2O)C(=O)C)O)c(c2c1OC(C)(C)C=C2)O)/C=C/c1ccccc1
• InChI: InChI=1S/C30H28O8/c1-15-24(33)19(27(36)22(16(2)31)25(15)34)14-20-26(35)18-12-13-30(3,4)38-29(18)23(28(20)37)21(32)11-10-17-8-6-5-7-9-17/h5-13,33-37H,14H2,1-4H3
• InChIKey: DEZFNHCVIZBHBI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl}-3-phenylprop-2-en-1-one; (2E)-1-{6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-chromen-8-yl}-3-phenylprop-2-en-1-one
• IUPAC Traditional name: 1-{6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethylchromen-8-yl}-3-phenylprop-2-en-1-one; rottlerin
• Synonyms: MALLOTOXIN; Rottlerin; 1-[6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one; Mallotoxin; Rottlerin

Database IDs

• CAS Number: 82-08-6
• EC Number: 201-395-4
• MDL Number: MFCD00017361
• PubChem SID: 162096275; 24278679
• PubChem CID: 5281847
• Chemspider ID: 4445144
• Wikipedia Title: Rottlerin

CALCULATED PROPERTIES

• Acid pKa: 6.3252997
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 7.3257732
• LogD (pH = 7.4): 6.2199435
• Log P: 7.385985
• Molar Refractivity: 146.3561 cm^3
• Polarizability: 54.222088 Å^3
• Polar Surface Area: 144.52 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: AM6913800
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... CDK2(1017)

Product Information

• Purity: ≥85%

DETAILS

MP Biomedicals - 05210865

MP Biomedicals Rare Chemical collection

Sigma Aldrich - R5648

Biochem/physiol Actions
Recently, Rottlerin (mallotoxin) has been shown to be a potent activator of the large conductance voltage and Ca2 activated K+ channel and to potently leftward shift the conductance-voltage relationship of the channel. Mallatoxin tested on hERG channels increased both step and tail hERG current by leftward shifting the voltage dependence of hERG activation and slowing channel deactivation. These actions distinguish Mallatoxin as a novel naturally occurring hERG channel activator.