pentyl 2-(3,5-dihydroxy-2-nonanoylphenyl)acetate

• ChemBase ID: 154752
• Molecular Formular: C22H34O5
• Molecular Mass: 378.50236
• Monoisotopic Mass: 378.24062419
• SMILES: CCCCCCCCC(=O)c1c(cc(cc1O)O)CC(=O)OCCCCC
• Canonical SMILES: CCCCCCCCC(=O)c1c(O)cc(cc1CC(=O)OCCCCC)O
• InChI: InChI=1S/C22H34O5/c1-3-5-7-8-9-10-12-19(24)22-17(14-18(23)16-20(22)25)15-21(26)27-13-11-6-4-2/h14,16,23,25H,3-13,15H2,1-2H3
• InChIKey: FCKDHZVFIMRCNM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: pentyl 2-(3,5-dihydroxy-2-nonanoylphenyl)acetate
• IUPAC Traditional name: pentyl 2-(3,5-dihydroxy-2-nonanoylphenyl)acetate
• Synonyms: Cytosporone A n-amyl ester; compound 10i; n-Amyl 2-[3,5-dihydroxy-2-(1-nonanoyl)phenyl]acetate

Database IDs

• MDL Number: MFCD18632550
• PubChem SID: 162248890
• PubChem CID: 67448541

CALCULATED PROPERTIES

• Acid pKa: 7.80963
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 6.4917116
• LogD (pH = 7.4): 6.352122
• Log P: 6.4938207
• Molar Refractivity: 107.2068 cm^3
• Polarizability: 41.81772 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: >65 mg/mL
• Apperance: white powder

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H34O5

DETAILS

Sigma Aldrich - A0987

Biochem/physiol Actions
n-Amyl 2-[3,5-dihydroxy-2-(1-nonanoyl)phenyl]acetate is a Nur77 agonist. Nur77 is a steroid orphan receptor that plays a critical role in regulating proliferation, differentiation and apoptosis. n-Amyl 2-[3,5-dihydroxy-2-(1-nonanoyl)phenyl]acetate, a cytosporone B analog, is a stronger activator of Nur77 than it parent compound. n-Amyl 2-[3,5-dihydroxy-2-(1-nonanoyl)phenyl]acetate treatment causes Nur77 migration to mitochondria, which results in mitochondrial Cyt c release into the cytoplasm and mitochondrial AIF redistribution in both the cytoplasm and nucleus.