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Identification
- Generic Name
- (2E,4E)-11-METHOXY-3,7,11-TRIMETHYLDODECA-2,4-DIENOIC ACID
- DrugBank Accession Number
- DB08175
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for (2E,4E)-11-METHOXY-3,7,11-TRIMETHYLDODECA-2,4-DIENOIC ACID (DB08175)
- Weight
- Average: 268.3917
Monoisotopic: 268.203844762 - Chemical Formula
- C16H28O3
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Target Actions Organism UNuclear receptor coactivator 2 Not Available Humans URetinoic acid receptor RXR-beta Not Available Humans UOxysterols receptor LXR-alpha Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Sesquiterpenoids
- Direct Parent
- Sesquiterpenoids
- Alternative Parents
- Medium-chain fatty acids / Methyl-branched fatty acids / Unsaturated fatty acids / Monocarboxylic acids and derivatives / Dialkyl ethers / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aliphatic acyclic compound / Branched fatty acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dialkyl ether / Ether / Farsesane sesquiterpenoid / Fatty acid / Fatty acyl
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- MB9LR353F8
- CAS number
- Not Available
- InChI Key
- MNYBEULOKRVZKY-ATCPXPEISA-N
- InChI
- InChI=1S/C16H28O3/c1-13(10-7-11-16(3,4)19-5)8-6-9-14(2)12-15(17)18/h6,9,12-13H,7-8,10-11H2,1-5H3,(H,17,18)/b9-6+,14-12+/t13-/m1/s1
- IUPAC Name
- (2E,4E,7S)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid
- SMILES
- COC(C)(C)CCC[C@@](C)([H])C\C=C\C(\C)=C\C(O)=O
References
- General References
- Not Available
- External Links
- PubChem Compound
- 5288795
- PubChem Substance
- 99444646
- ChemSpider
- 4450887
- ZINC
- ZINC000002244163
- PDBe Ligand
- MEI
- PDB Entries
- 1uhl
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00868 mg/mL ALOGPS logP 5.18 ALOGPS logP 4.1 Chemaxon logS -4.5 ALOGPS pKa (Strongest Acidic) 4.82 Chemaxon pKa (Strongest Basic) -4.1 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 46.53 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 80.86 m3·mol-1 Chemaxon Polarizability 32.11 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9493 Blood Brain Barrier + 0.8798 Caco-2 permeable + 0.6882 P-glycoprotein substrate Substrate 0.5275 P-glycoprotein inhibitor I Non-inhibitor 0.7425 P-glycoprotein inhibitor II Inhibitor 0.6548 Renal organic cation transporter Non-inhibitor 0.8739 CYP450 2C9 substrate Non-substrate 0.8524 CYP450 2D6 substrate Non-substrate 0.9031 CYP450 3A4 substrate Substrate 0.6124 CYP450 1A2 substrate Non-inhibitor 0.8305 CYP450 2C9 inhibitor Non-inhibitor 0.8003 CYP450 2D6 inhibitor Non-inhibitor 0.9503 CYP450 2C19 inhibitor Non-inhibitor 0.871 CYP450 3A4 inhibitor Non-inhibitor 0.9086 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9121 Ames test Non AMES toxic 0.8874 Carcinogenicity Non-carcinogens 0.5799 Biodegradation Ready biodegradable 0.7087 Rat acute toxicity 1.3231 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9399 hERG inhibition (predictor II) Non-inhibitor 0.8858
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00di-9340000000-0b32ea76c1169199b12f Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-014u-1690000000-0830d20e8bebccb64dd7 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0090000000-ada0567337213ba0dabe Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00xu-2490000000-4e5cd7721d8d33e6b757 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4l-3910000000-6e6c576af225b1eb5ddf Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-05fr-4960000000-d681aea71fe07c46151a Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-053u-9600000000-2a43482a8bfa163d7c4f Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 171.77054 predictedDeepCCS 1.0 (2019) [M+H]+ 174.12854 predictedDeepCCS 1.0 (2019) [M+Na]+ 180.95546 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transcriptional coactivator for steroid receptors and nuclear receptors (PubMed:23508108, PubMed:8670870, PubMed:9430642). Coactivator of the steroid binding domain (AF-2) but not of the modulating N-terminal domain (AF-1) (PubMed:23508108, PubMed:8670870, PubMed:9430642). Required with NCOA1 to control energy balance between white and brown adipose tissues (PubMed:23508108, PubMed:8670870, PubMed:9430642). Critical regulator of glucose metabolism regulation, acts as a RORA coactivator to specifically modulate G6PC1 expression (PubMed:23508108, PubMed:8670870, PubMed:9430642). Involved in the positive regulation of the transcriptional activity of the glucocorticoid receptor NR3C1 by sumoylation enhancer RWDD3 (PubMed:23508108). Positively regulates the circadian clock by acting as a transcriptional coactivator for the CLOCK-BMAL1 heterodimer (By similarity)
- Specific Function
- Aryl hydrocarbon receptor binding
- Gene Name
- NCOA2
- Uniprot ID
- Q15596
- Uniprot Name
- Nuclear receptor coactivator 2
- Molecular Weight
- 159155.645 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE)
- Specific Function
- Dna-binding transcription activator activity, rna polymerase ii-specific
- Gene Name
- RXRB
- Uniprot ID
- P28702
- Uniprot Name
- Retinoic acid receptor RXR-beta
- Molecular Weight
- 56921.38 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Nuclear receptor that exhibits a ligand-dependent transcriptional activation activity (PubMed:19481530, PubMed:25661920, PubMed:37478846). Interaction with retinoic acid receptor (RXR) shifts RXR from its role as a silent DNA-binding partner to an active ligand-binding subunit in mediating retinoid responses through target genes defined by LXRES (PubMed:37478846). LXRES are DR4-type response elements characterized by direct repeats of two similar hexanuclotide half-sites spaced by four nucleotides (By similarity). Plays an important role in the regulation of cholesterol homeostasis, regulating cholesterol uptake through MYLIP-dependent ubiquitination of LDLR, VLDLR and LRP8 (PubMed:19481530). Interplays functionally with RORA for the regulation of genes involved in liver metabolism (By similarity). Induces LPCAT3-dependent phospholipid remodeling in endoplasmic reticulum (ER) membranes of hepatocytes, driving SREBF1 processing and lipogenesis (By similarity). Via LPCAT3, triggers the incorporation of arachidonate into phosphatidylcholines of ER membranes, increasing membrane dynamics and enabling triacylglycerols transfer to nascent very low-density lipoprotein (VLDL) particles. Via LPCAT3 also counteracts lipid-induced ER stress response and inflammation, likely by modulating SRC kinase membrane compartmentalization and limiting the synthesis of lipid inflammatory mediators (By similarity)
- Specific Function
- Cholesterol binding
- Gene Name
- NR1H3
- Uniprot ID
- Q13133
- Uniprot Name
- Oxysterols receptor LXR-alpha
- Molecular Weight
- 50395.34 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at September 15, 2010 21:29 / Updated at June 12, 2020 16:52