Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H26O6 |
Molecular Weight | 362.4168 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(C[C@@H](CO)[C@H](CO)CC2=CC(OC)=C(O)C=C2)=CC=C1O
InChI
InChIKey=PUETUDUXMCLALY-HOTGVXAUSA-N
InChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16-/m0/s1
Molecular Formula | C20H26O6 |
Molecular Weight | 362.4168 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.hmdb.ca/metabolites/HMDB13692Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/21138310 | https://www.ncbi.nlm.nih.gov/pubmed/22658537 | https://www.ncbi.nlm.nih.gov/pubmed/21420296 | https://www.ncbi.nlm.nih.gov/pubmed/24429845
Sources: http://www.hmdb.ca/metabolites/HMDB13692
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/21138310 | https://www.ncbi.nlm.nih.gov/pubmed/22658537 | https://www.ncbi.nlm.nih.gov/pubmed/21420296 | https://www.ncbi.nlm.nih.gov/pubmed/24429845
Secoisolaricircsinol is one of the most abundant dietary lignans in various foods, such as plant seeds, whole grains, legumes, vegetables, and fruits. Secoisolariciresinol is the major lignin found in flaxseed and is present in a polymer that contains Secoisolariciresinol diglucoside. Secoisolariciresinol and Secoisolariciresinol diglucoside are known to have a number of health benefits, including reduction of the serum cholesterol levels, delaying of the onset of type 2 diabetes, and reduction of the formation of hormone-sensitive cancers such as breast, prostate, and colon cancers. Following the consumption of Secoisolariciresinol diglucoside, it is further converted by the bacteria in the colon of humans and other animals into aglycone Secoisolariciresinol and the mammalian lignans, enterodiol and enterolactone. The structures of enterodiol and enterolactone are similar to that of estradiol, an endogenous estrogen. This structural similarity accounts for the ability of these compounds to bind to estrogen receptors and to exert weak estrogenic or anti-estrogenic effects, depending on the presence of stronger estrogen. It is well known that Secoisolariciresinol has an estrogen-like activity and stimulates the cell growth of human breast cancer MCF-7 cells.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL332 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22658537 |
50.12 µM [IC50] | ||
Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21138310 |
47.3 µM [IC50] | ||
Target ID: CHEMBL1929 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16309309 |
213.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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New lignans from Anogeissus acuminata with HIV-1 reverse transcriptase inhibitory activity. | 1994 Jul |
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(-)-Arctigenin as a lead structure for inhibitors of human immunodeficiency virus type-1 integrase. | 1996 Jan 5 |
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Lignans, bacteriocides and organochlorine compounds activate the human pregnane X receptor (PXR). | 2005 Dec 1 |
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Endocrine disrupting effects in rats perinatally exposed to a dietary relevant mixture of phytoestrogens. | 2013 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23885143
20 mg secoisolariciresinol for 60 days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21420296
Four human tumor cell lines including A549 (non-small cell lung carcinoma), SK-OV-3 (ovary malignant ascites), SK-MEL-2 (skin melanoma), and XF498 (human CNS cancer) were used for activity evaluation. Cells were treated with Secoisolaricircsinol (0.1-100mkM) and compound activity was evaluated using a sulforhodamine B (SRB) assay. Secoisolaricircsinol showed cytotoxicity against SK-MEL-2 and XF498 cell lines with IC50 values of 21.47 and , 18.7 mkM, respectively
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:51:12 GMT 2023
by
admin
on
Fri Dec 15 19:51:12 GMT 2023
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Record UNII |
M8QRJ7JEJH
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Record Status |
Validated (UNII)
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Record Version |
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C63638
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SECOISOLARICIRESINOL
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C060283
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C68495
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