2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione

• ChemBase ID: 154384
• Molecular Formular: C17H26O4
• Molecular Mass: 294.38594
• Monoisotopic Mass: 294.18310931
• SMILES: CCCCCCCCCCCC1=C(C(=O)C=C(C1=O)O)O
• Canonical SMILES: CCCCCCCCCCCC1=C(O)C(=O)C=C(C1=O)O
• InChI: InChI=1S/C17H26O4/c1-2-3-4-5-6-7-8-9-10-11-13-16(20)14(18)12-15(19)17(13)21/h12,18,21H,2-11H2,1H3
• InChIKey: IRSFLDGTOHBADP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dihydroxy-3-undecylcyclohexa-2,5-diene-1,4-dione
• IUPAC Traditional name: embelin
• Synonyms: Embelic Acid; Embelin; 2,5-Dihydroxy-3-undecyl-2,5-cyclohexadiene-1,4-dione; Embelin

Database IDs

• CAS Number: 550-24-3
• EC Number: 208-979-8
• MDL Number: MFCD00016369
• PubChem SID: 162248523; 24724473
• PubChem CID: 3218

CALCULATED PROPERTIES

• Acid pKa: 5.3630805
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.453348
• LogD (pH = 7.4): 2.8008964
• Log P: 4.8280354
• Molar Refractivity: 85.3307 cm^3
• Polarizability: 32.21666 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble
• Apperance: powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Target: IAP
• Gene Information: human ... XIAP(331)

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C17H26O4

DETAILS

Sigma Aldrich - E1406

Biochem/physiol Actions
Embelin is an inhibitor of XIAP (X-linked inhibitor-of-apoptosis protein); in vivo antitumor and anti-inflammatory activity.