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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
Structure of SECOISOLARICIRESINOL

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

HIDE SMILES / InChI

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

Description
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

Sources: Tetrahedron Letters (1959), 4, 14-15.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
50.12 µM [IC50]
47.3 µM [IC50]
213.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
New lignans from Anogeissus acuminata with HIV-1 reverse transcriptase inhibitory activity.
1994 Jul
(-)-Arctigenin as a lead structure for inhibitors of human immunodeficiency virus type-1 integrase.
1996 Jan 5
Lignans, bacteriocides and organochlorine compounds activate the human pregnane X receptor (PXR).
2005 Dec 1
Endocrine disrupting effects in rats perinatally exposed to a dietary relevant mixture of phytoestrogens.
2013 Sep
Patents

Sample Use Guides

20 mg secoisolariciresinol for 60 days
Route of Administration: Oral
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 Fri Dec 15 19:51:12 GMT 2023
Edited
by admin
on Fri Dec 15 19:51:12 GMT 2023
Record UNII
M8QRJ7JEJH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SECOISOLARICIRESINOL
Common Name English
(8R,8'R)-(-)-SECOISOLARICIRESINOL
Common Name English
(-)-SECOISOLARICIRESINOL
Common Name English
1,4-BUTANEDIOL, 2,3-DIVANILLYL-, (-)-
Systematic Name English
1,4-BUTANEDIOL, 2,3-BIS((4-HYDROXY-3-METHOXYPHENYL)METHYL)-, (R-(R*,R*))-
Common Name English
SECOISOLARICIRESINOL, (-)-
Common Name English
SECO-ISOLARICIRESINOL
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C63638
Created by admin on Fri Dec 15 19:51:12 GMT 2023 , Edited by admin on Fri Dec 15 19:51:12 GMT 2023
Code System Code Type Description
FDA UNII
M8QRJ7JEJH
Created by admin on Fri Dec 15 19:51:12 GMT 2023 , Edited by admin on Fri Dec 15 19:51:12 GMT 2023
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DRUG BANK
DB12179
Created by admin on Fri Dec 15 19:51:12 GMT 2023 , Edited by admin on Fri Dec 15 19:51:12 GMT 2023
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ECHA (EC/EINECS)
249-599-2
Created by admin on Fri Dec 15 19:51:12 GMT 2023 , Edited by admin on Fri Dec 15 19:51:12 GMT 2023
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PUBCHEM
65373
Created by admin on Fri Dec 15 19:51:12 GMT 2023 , Edited by admin on Fri Dec 15 19:51:12 GMT 2023
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CAS
29388-59-8
Created by admin on Fri Dec 15 19:51:12 GMT 2023 , Edited by admin on Fri Dec 15 19:51:12 GMT 2023
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CHEBI
65004
Created by admin on Fri Dec 15 19:51:12 GMT 2023 , Edited by admin on Fri Dec 15 19:51:12 GMT 2023
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EPA CompTox
DTXSID50183615
Created by admin on Fri Dec 15 19:51:12 GMT 2023 , Edited by admin on Fri Dec 15 19:51:12 GMT 2023
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WIKIPEDIA
SECOISOLARICIRESINOL
Created by admin on Fri Dec 15 19:51:12 GMT 2023 , Edited by admin on Fri Dec 15 19:51:12 GMT 2023
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MESH
C060283
Created by admin on Fri Dec 15 19:51:12 GMT 2023 , Edited by admin on Fri Dec 15 19:51:12 GMT 2023
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NCI_THESAURUS
C68495
Created by admin on Fri Dec 15 19:51:12 GMT 2023 , Edited by admin on Fri Dec 15 19:51:12 GMT 2023
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