3-{[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]methyl}-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione

• ChemBase ID: 105375
• Molecular Formular: C22H30O4
• Molecular Mass: 358.4712
• Monoisotopic Mass: 358.21440944
• SMILES: C=C1CCC[C@@H]2[C@]1(C)CC[C@H](C)[C@@]2(C)CC1=C(C(=O)C=C(C1=O)OC)O
• Canonical SMILES: COC1=CC(=O)C(=C(C1=O)C[C@]1(C)[C@@H](C)CC[C@]2([C@H]1CCCC2=C)C)O
• InChI: InChI=1S/C22H30O4/c1-13-7-6-8-18-21(13,3)10-9-14(2)22(18,4)12-15-19(24)16(23)11-17(26-5)20(15)25/h11,14,18,24H,1,6-10,12H2,2-5H3/t14-,18+,21+,22+/m0/s1
• InChIKey: JJWITJNSXCXULM-YVUMSICPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]methyl}-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
• IUPAC Traditional name: 3-{[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]methyl}-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
• Synonyms: ILIMAQUINONE; 3-[(Decahydro-1β,2β,4aβ-trimethyl-5-methylene-1-naphthyl)methyl]-2-hydroxy-5-methoxybenzoquinone; Ilimaquinone

Database IDs

• CAS Number: 71678-03-0
• MDL Number: MFCD00274432
• PubChem SID: 24896109; 162092114
• PubChem CID: 72291

CALCULATED PROPERTIES

• Acid pKa: 8.368667
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.366662
• LogD (pH = 7.4): 4.3229265
• Log P: 4.367249
• Molar Refractivity: 104.1452 cm^3
• Polarizability: 39.79424 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: 99%

DETAILS

MP Biomedicals - 02159947

Purity: 99%
Completely and reversibly induces the breakdown of Golgi membranes. Inhibits the association of β-COP and ADP-ribosylation factor to Golgi membranes. It does not induce the redistribution of Golgi membranes into the endoplasmic re

Sigma Aldrich - I7146

Biochem/physiol Actions
Induces reversible breakdown of Golgi membranes.