Basic information
- CAS
71678-03-0- Standard SMILES
C=C1CCC[C@H]2[C@](C)(CC3=C(O)C(=O)C=C(OC)C3=O)[C@@H](C)CC[C@]12C- InChIKey
JJWITJNSXCXULM-YVUMSICPSA-N- Molecular formula
- C22H30O4
- Average molar mass
- 358.5 g/mol
- Monoisotopic mass
- 358.21440943
Overview
Ilimaquinone is a prenylquinone and a member of monohydroxy-1,4-benzoquinones. It has a role as a metabolite.
Names & identifiers
- Preferred name
- Ilimaquinone
- IUPAC
- 3-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
- English name
- ILIMAQUINONE
- Molecular formula
- C22H30O4
- Molecular weight
- 358.47
Names & synonyms
ilimaquinone71678-03-0Illimaquinone5U0WAN3N8Q3-[[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dioneDTXSID902219092,5-Cyclohexadiene-1,4-dione, 3-((decahydro-1,2,4a-trimethyl-5-methylene-1-naphthalenyl)methyl)-2-hydroxy-5-methoxy-, (1R-(1alpha,2beta,4abeta,8aalpha))-3-(((1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-3,4,6,7,8,8a-hexahydro-2H-naphthalen-1-yl)methyl)-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dioneRefChem:147865DTXCID701444002-Hydroxy-5-methoxy-3-(((1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylenedecahydronaphthalen-1-yl)methyl)cyclohexa-2,5-diene-1,4-dioneImaquinone
Show more names
IQ(-)-Ilimaquinine(-)-ILIMAQUINONE5-EpiilimaquinoneIlimaquinone - CAS 71678-03-0 - CalbiochemIlimaquinone, Cytoplasmic microtubule inhibitor3-[(decahydro-1β,2β,4aβ-trimethyl-5-methylene-1-naphthyl)methyl]-2-hydroxy-5-methoxybenzoquinone
Properties
Computed structural properties
- XLogP
- 5.1
- Topological polar surface area
- 63.6 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 728
Physicochemical properties
- Melting point
- 108 · 108-110℃ (pentane )
- alpha
- 23 · D23 -23.2° (c = 1.12 in CHCl3)
- Boiling point
- 478.4 · 478.4±45.0 °C(Predicted)
- Density
- 1.14 · 1.14±0.1 g/cm3(Predicted)
- storage temp.
- 20 °C · −20°C
- solubility
- DMSO: Soluble; Ethanol: Soluble; Hexane: Soluble; Methanol: Soluble
- pka
- 2.92 · 2.92±0.50(Predicted)
- form
- Red solid
- color
- Light yellow to brown
- 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
- FDA UNII
- 5 U0WAN3N8Q · 5U0WAN3N8Q
- Proposition 65 List
- IQ (2-Amino-3-methylimidazo-[4-5-f]quinoline)
- UNSPSC Code
- 12352200 · 12352200
- NACRES
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
DescriptionIlimaquinone is a natural sesquiterpene quinone that has antimicrobial, anti-HIV, anti-mitotic, and anti-inflammatory properties. In mammalian cells, 25 μM ilimaquinone reversibly induces vesiculation of Golgi membranes, blocking the secretory pathway. It inhibits the conversion of S-adenosylhomocysteine (SAH) to homocysteine by SAH hydrolase (IC50 = 40 μM). Ilimaquinone also inhibits DNA polymerase β and dual specificity phosphatase Cdc25B (IC50 = 45.2 and 92 μM, respectively) and, at 10 μM, activates gene expression through hypoxia-inducible factor-1.
UsesIlimaquinone is an ADP-ribosylation factor (ARF) and β-COP to the Golgi membrane inhibitor.
UsesBiological probe for intracellular communications and vesicle-mediated transport.
General DescriptionA cell-permeable marine sponge metabolite with anti-microbial, anti-HIV, anti-inflammatory, and anti-mitotic properties. Induces a complete and reversible breakdown of Golgi membranes into smaller vesicular structures and causes depolymerization of microtubules. Inhibits cellular methylations through its interaction with S-adenosylhomocysteinase. Blocks the cytotoxicity of ricin and diphtheria toxin. Acts as an inhibitor of the RNase H activity of HIV-1.
Suppliers9 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
Aladdin Scientific[email protected]
上海皓骏医药科技有限公司021-34621078 13120882795 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
TargetMol中国（陶术生物）
Related reactions
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Compound notes
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