Cannabielsoin
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Basic Info
| Common Name | Cannabielsoin(F04640) |
| 2D Structure | |
| Description | Chlorinated dibenzofurans (CDFs) are a family of chemical that contain one to eight chlorine atoms attached to the carbon atoms of the parent chemical, dibenzofuran. The CDF family contains 135 individual compounds (known as congeners) with varying harmful health and environmental effects. Of these 135 compounds, those that contain chlorine atoms at the 2,3,7,8-positions of the parent dibenzofuran molecule are especially harmful. Other than for laboratory use of small amounts of CDFs for research and development purposes, these chemicals are not deliberately produced by industry. Most CDFs are produced in very small amounts as unwanted impurities of certain products and processes utilizing chlorinated compounds. Only a few of the 135 CDF compounds have been produced in large enough quantities so that their properties, such as color, smell, taste, and toxicity could be studied. (L952) |
| FRCD ID | F04640 |
| CAS Number | 52025-76-0 |
| PubChem CID | 162113 |
| Formula | C21H30O3 |
| IUPAC Name | (5aS,6S,9R,9aR)-6-methyl-3-pentyl-9-prop-1-en-2-yl-7,8,9,9a-tetrahydro-5aH-dibenzofuran-1,6-diol |
| InChI Key | RBEAVAMWZAJWOI-MTOHEIAKSA-N |
| InChI | InChI=1S/C21H30O3/c1-5-6-7-8-14-11-16(22)19-17(12-14)24-20-18(19)15(13(2)3)9-10-21(20,4)23/h11-12,15,18,20,22-23H,2,5-10H2,1,3-4H3/t15-,18+,20-,21-/m0/s1 |
| Canonical SMILES | CCCCCC1=CC2=C(C3C(CCC(C3O2)(C)O)C(=C)C)C(=C1)O |
| Isomeric SMILES | CCCCCC1=CC2=C([C@H]3[C@@H](CC[C@]([C@H]3O2)(C)O)C(=C)C)C(=C1)O |
| Synonyms |
(5as,6s,9r,9ar)-6-methyl-3-pentyl-9-(prop-1-en-2-yl)-5a,6,7,8,9,9a-hexahydrodibenzo[b,d]furan-1,6-diol
Cannabielsoin
Cannabielsoin A
52025-76-0
AC1L4QPR
SCHEMBL13214152
CTK4J9282
RBEAVAMWZAJWOI-MTOHEIAKSA-N
C20218
(5aS,6S,9R,9aR)-6-methyl-3-pentyl-9-prop-1-en-2-yl-7,8,9,9a-tetrahydro-5aH-dibenzofuran-1,6-diol
|
| Classifies |
Pollutant
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Monoterpenoids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Aromatic monoterpenoids |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Aromatic monoterpenoid - P-menthane monoterpenoid - Coumaran - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Benzenoid - Cyclic alcohol - Tertiary alcohol - Ether - Oxacycle - Organoheterocyclic compound - Organic oxygen compound - Organooxygen compound - Alcohol - Hydrocarbon derivative - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 330.468 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 5 |
| Complexity | 462 |
| Monoisotopic Mass | 330.219 |
| Exact Mass | 330.219 |
| XLogP | 5.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 24 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9379 |
| Human Intestinal Absorption | HIA+ | 0.9964 |
| Caco-2 Permeability | Caco2+ | 0.6426 |
| P-glycoprotein Substrate | Substrate | 0.8896 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.5569 |
| Non-inhibitor | 0.6792 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8522 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.5131 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8145 |
| CYP450 2D6 Substrate | Non-substrate | 0.8404 |
| CYP450 3A4 Substrate | Substrate | 0.6997 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.5906 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6129 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8462 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.5856 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.5660 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7711 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9187 |
| Non-inhibitor | 0.6460 | |
| AMES Toxicity | Non AMES toxic | 0.7206 |
| Carcinogens | Non-carcinogens | 0.9090 |
| Fish Toxicity | High FHMT | 0.9928 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9980 |
| Honey Bee Toxicity | High HBT | 0.7988 |
| Biodegradation | Not ready biodegradable | 0.9938 |
| Acute Oral Toxicity | III | 0.4611 |
| Carcinogenicity (Three-class) | Non-required | 0.4823 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.3585 | LogS |
| Caco-2 Permeability | 1.2635 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.8849 | LD50, mol/kg |
| Fish Toxicity | 0.1323 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.1541 | pIGC50, ug/L |
Targets
- General Function:
- Transcription regulatory region dna binding
- Specific Function:
- Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues. Regulates the circadian clock by inhibiting the basal and circadian expression of the core circadian component PER1. Inhibits PER1 by repressing the CLOCK-ARNTL/BMAL1 heterodimer mediated transcriptional activation of PER1.
- Gene Name:
- AHR
- Uniprot ID:
- P35869
- Molecular Weight:
- 96146.705 Da
- Mechanism of Action:
- Dibenzofurans bind the aryl hydrocarbon receptor, which increases its ability to activate transcription in the XRE promoter region. This alters the expression of a number of genes.
References
- Ni J, Pang ST, Yeh S: Differential retention of alpha-vitamin E is correlated with its transporter gene expression and growth inhibition efficacy in prostate cancer cells. Prostate. 2007 Apr 1;67(5):463-71. [17252538 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560). Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
- Gene Name:
- ESR2
- Uniprot ID:
- Q92731
- Molecular Weight:
- 59215.765 Da
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
- Gene Name:
- ESR1
- Uniprot ID:
- P03372
- Molecular Weight:
- 66215.45 Da
- Mechanism of Action:
- Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor.
References
- Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [16531984 ]
- General Function:
- Temperature-gated cation channel activity
- Specific Function:
- Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
- Gene Name:
- TRPA1
- Uniprot ID:
- O75762
- Molecular Weight:
- 127499.88 Da
References
- Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]