Etrinabdione (EHP-101; VCE004.8; VCE-004.8) is a semi-synthetic multitarget cannabinoquinoid, acting as a specific PPARγ and CB2 receptor dual agonist with potent anti-inflammatory activity. While activating the HIF pathway, VCE-004.8 inhibits prolyl-hydroxylases (PHDs). Avoiding diet-induced obesity, VCE-004.8 attenuates adipogenesis.
Physicochemical Properties
| Molecular Formula | C28H35NO3 |
| Molecular Weight | 433.582408189774 |
| Exact Mass | 433.26 |
| Elemental Analysis | C, 77.56; H, 8.14; N, 3.23; O, 11.07 |
| CAS # | 1818428-24-8 |
| Related CAS # | 1818428-24-8 |
| PubChem CID | 118465221 |
| Appearance | Dark purple to black solid powder |
| LogP | 6.3 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 9 |
| Heavy Atom Count | 32 |
| Complexity | 839 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | CCCCCC1=C(C(=C(C(=O)C1=O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O)NCC3=CC=CC=C3 |
| InChi Key | CGGGAXJIRQSRPH-JTHBVZDNSA-N |
| InChi Code | InChI=1S/C28H35NO3/c1-5-6-8-13-22-25(29-17-20-11-9-7-10-12-20)27(31)24(28(32)26(22)30)23-16-19(4)14-15-21(23)18(2)3/h7,9-12,16,21,23,29,31H,2,5-6,8,13-15,17H2,1,3-4H3/t21-,23+/m0/s1 |
| Chemical Name | 5-(benzylamino)-4-hydroxy-3-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-6-pentylcyclohexa-3,5-diene-1,2-dione |
| Synonyms | etrinabdione; EHP-101; EHP101; VCE-004; EHP 101; VCE004; VCE 004; VCE004.8; VCE 004.8; VCE-004.8 |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | PPARγ; CB2 |
| ln Vivo | Etrinabdione (i.p.; 20 mg/kg/day; for 3 weeks) causes a notable decrease in body weight gain, total fat mass, adipocyte volume, and plasma triglyceride levels over the course of three weeks in HFD mice. Additionally, etrinabdione has been shown to significantly improve glucose tolerance, lower levels of leptin, an adiposity marker, and raise levels of adiponectin, incretins (GLP-1 and GIP), and adiponectin[1]. |
| References |
[1]. Hypoxia mimetic activity of VCE-004.8, a cannabidiol quinone derivative: implications for multiple sclerosis therapy. J Neuroinflammation. 2018 Mar 1;15(1):64. [2]. VCE-004.8, A Multitarget Cannabinoquinone, Attenuates Adipogenesis and Prevents Diet-Induced Obesity. Sci Rep. 2018 Oct 31;8(1):16092. |
Solubility Data
| Solubility (In Vitro) | DMSO: ~50 mg/mL (~115.3 mM） |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (5.77 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (5.77 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (5.77 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.3064 mL | 11.5319 mL | 23.0638 mL | |
| 5 mM | 0.4613 mL | 2.3064 mL | 4.6128 mL | |
| 10 mM | 0.2306 mL | 1.1532 mL | 2.3064 mL |