O-Desmethylangolensin
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Basic Info
| Common Name | O-Desmethylangolensin(F05166) |
| 2D Structure | |
| Description | O-Desmethylangolensin (ODMA) is a metabolite of the soy isoflavone daidzein by intestinal bacteria in approximately 80-90% of persons. Studies suggest beneficial health effects associated with daidzein-metabolizing phenotypes, and there is some small association between ODMA production and some phenotypes. Few dietary factors are associated with daidzein-metabolizing phenotypes. However, it remains unclear why some, but not all, persons harbor ODMA-producing bacteria. ODMA production is inversely associated with age, height, weight, and body mass index. In addition, Asians are less likely than whites to be ODMA producers, and former smokers were more likely than never smokers to be ODMA producers. Investigators have attempted to identify the bacteria involved in ODMA production, and several candidate bacteria were associated, but not definitely identified. ODMA production is correlated with the abundance of methanogens, indicating that the metabolic fate of daidzein may be related to intestinal H(2) metabolism. (A3192, A3193). |
| FRCD ID | F05166 |
| CAS Number | 21255-69-6 |
| PubChem CID | 89472 |
| Formula | C15H14O4 |
| IUPAC Name | 1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one |
| InChI Key | JDJPNKPFDDUBFV-UHFFFAOYSA-N |
| InChI | InChI=1S/C15H14O4/c1-9(10-2-4-11(16)5-3-10)15(19)13-7-6-12(17)8-14(13)18/h2-9,16-18H,1H3 |
| Canonical SMILES | CC(C1=CC=C(C=C1)O)C(=O)C2=C(C=C(C=C2)O)O |
| Isomeric SMILES | CC(C1=CC=C(C=C1)O)C(=O)C2=C(C=C(C=C2)O)O |
| Synonyms |
1-Propanone, 1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)-
O-Desmethylangolensin
o-demethylangolensin
21255-69-6
1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one
O-Demethylangolesin
AC1L3HY3
AC1Q5ED8
SCHEMBL677731
SCHEMBL12255054
|
| Classifies |
Animal Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Phenylpropanoids and polyketides |
| Class | Alpha-methyldeoxybenzoin flavonoids |
| Subclass | Not available |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Alpha-methyldeoxybenzoin flavonoids |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Alpha-methyldeoxybenzoin flavonoid - Stilbene - Alkyl-phenylketone - Phenylketone - Phenylpropane - Benzoyl - Aryl alkyl ketone - Aryl ketone - Resorcinol - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Monocyclic benzene moiety - Benzenoid - Vinylogous acid - Ketone - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Organic oxygen compound - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as alpha-methyldeoxybenzoin flavonoids. These are flavonoids with a structure based on a 1,2-diphenyl-2-propan-2-one. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 258.273 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 3 |
| Complexity | 309 |
| Monoisotopic Mass | 258.089 |
| Exact Mass | 258.089 |
| XLogP | 3.3 |
| Formal Charge | 0 |
| Heavy Atom Count | 19 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 1 |
| 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+ | 0.6150 |
| Human Intestinal Absorption | HIA+ | 0.9875 |
| Caco-2 Permeability | Caco2+ | 0.8966 |
| P-glycoprotein Substrate | Non-substrate | 0.5556 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9381 |
| Non-inhibitor | 0.9671 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8843 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8873 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6881 |
| CYP450 2D6 Substrate | Non-substrate | 0.8990 |
| CYP450 3A4 Substrate | Non-substrate | 0.6575 |
| CYP450 1A2 Inhibitor | Inhibitor | 0.9266 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.8820 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9047 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.8215 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.6496 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7280 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9460 |
| Non-inhibitor | 0.9294 | |
| AMES Toxicity | Non AMES toxic | 0.9112 |
| Carcinogens | Non-carcinogens | 0.8415 |
| Fish Toxicity | High FHMT | 0.9148 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9913 |
| Honey Bee Toxicity | High HBT | 0.6739 |
| Biodegradation | Not ready biodegradable | 0.6818 |
| Acute Oral Toxicity | III | 0.8425 |
| Carcinogenicity (Three-class) | Non-required | 0.7616 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.5888 | LogS |
| Caco-2 Permeability | 1.0950 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.0353 | LD50, mol/kg |
| Fish Toxicity | 0.1726 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 1.1151 | pIGC50, ug/L |
Targets
- 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
- 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