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Secoisolariciresinol

PubChem CID: 65373

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Compound Synonyms Secoisolariciresinol, 29388-59-8, (-)-Secoisolariciresinol, (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol, 1,4-Butanediol, 2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-, (2R,3R)-, M8QRJ7JEJH, CHEMBL368347, CHEBI:65004, (2R,3R)-2,3-bis(4-hydroxy-3-methoxybenzyl)butane-1,4-diol, (2R*,3R*)-2,3-Bis(4-hydroxy-3-methoxybenzyl)-1,4-butanediol, (2R,3R)-2,3-bis[(3-methoxy-4-oxidanyl-phenyl)methyl]butane-1,4-diol, CCRIS 7790, (+/-)-Secoisolariciresinol, UNII-M8QRJ7JEJH, EINECS 249-599-2, GO6, RR-secoisolariciresinol, (-) secoisolariciresinol, secoisolariciresinol-(-), 8R,8'R-secoisolariciresinol, MLS001424213, SCHEMBL12427083, DTXSID50183615, HMS2052G03, HMS2232J05, HY-N6071, SECOISOLARICIRESINOL, (-)-, BDBM50240914, MFCD01075136, (R-(R*,R*))-2,3-Bis((4-hydroxy-3-methoxyphenyl)methyl)butane-1,4-diol, AKOS032948353, CCG-101074, DB12179, FS65512, NC00324, 1,4-Butanediol, 2,3-bis((4-hydroxy-3-methoxyphenyl)methyl)-, (R-(R*,R*))-, NCGC00346838-01, AS-78311, DA-67513, Secoisolariciresinol, >=95.0% (HPLC), SMR000469212, (8R,8'R)-(-)-SECOISOLARICIRESINOL, CS-0032316, NS00028683, 4,4',9,9'-Tetrhydroxy-3,3'-dimethoxylignan, C18167, A876479, 1,4-BUTANEDIOL, 2,3-DIVANILLYL-, (-)-, Q4413253, BRD-K91733562-001-05-0, 2,3-Bis(4-hydroxy-3-methoxybenzyl)-1,4-butanediol, (-), (2R,3R)-2,3-bis[(4-hydroxy-3-methoxy-phenyl)methyl]butane-1,4-diol, 1,4-Butanediol,2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-, (2R,3R)-
Ghose Rule True
Classyfire Kingdom Organic compounds
Topological Polar Surface Area 99.4
Hydrogen Bond Donor Count 4.0
Pfizer 3 75 Rule True
Scaffold Graph Level C1CCC(CCCCC2CCCCC2)CC1
Np Classifier Class Dibenzylbutane lignans
Deep Smiles OC[C@@H][C@@H]Ccccccc6)OC)))O))))))CO)))Ccccccc6)OC)))O
Heavy Atom Count 26.0
Classyfire Class Dibenzylbutane lignans
Description Secoisolariciresinol, also known as knotolan or secoisolariciresinol, (r*,s*)-isomer, is a member of the class of compounds known as dibenzylbutanediol lignans. Dibenzylbutanediol lignans are lignan compounds containing a 2,3-dibenzylbutane-1,4-diol moiety. Secoisolariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Secoisolariciresinol can be found in a number of food items such as grape, saskatoon berry, asparagus, and sweet potato, which makes secoisolariciresinol a potential biomarker for the consumption of these food products. Secoisolariciresinol can be found primarily in urine. Secoisolariciresinol is a lignan, a type of phenylpropanoid. It is present in the water extract of silver fir wood, where its content is more than 5 % .
Scaffold Graph Node Level C1CCC(CCCCC2CCCCC2)CC1
Classyfire Subclass Dibenzylbutanediol lignans
Isotope Atom Count 0.0
Molecular Complexity 356.0
Database Name cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem
Defined Atom Stereocenter Count 2.0
Uniprot Id Q7ZJM1, n.a., P47989, P04278, P08684, P10635, P03956, P0DTD1
Iupac Name (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol
Prediction Hob 0.0
Class Dibenzylbutane lignans
Veber Rule True
Classyfire Superclass Lignans, neolignans and related compounds
Target Id NPT967, NPT895, NPT109, NPT69
Xlogp 2.5
Superclass Lignans, neolignans and related compounds
Subclass Dibenzylbutanediol lignans
Gsk 4 400 Rule True
Molecular Formula C20H26O6
Scaffold Graph Node Bond Level c1ccc(CCCCc2ccccc2)cc1
Prediction Swissadme 0.0
Inchi Key PUETUDUXMCLALY-HOTGVXAUSA-N
Silicos It Class Moderately soluble
Fcsp3 0.4
Logs -2.672
Rotatable Bond Count 9.0
Logd 2.158
Synonyms (-)-Secoisolariciresinol, Secoisolariciresinol, (+)-Secoisolariciresinol, 2,3-Bis((4-hydroxy-3-methoxyphenyl)methyl)-1,4-butanediol, Knotolan, Secoisolariciresinol, (r*,s*)-isomer, (8R,8'R)-(-)-Secoisolariciresinol, (8R,8’R)-(-)-Secoisolariciresinol, seco-Isolariciresinol, 2,3-Bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol, 2,3-Divanillyl-1,4-butanediol, (-)-secoisolariciresinol, --secoisolariciresinol, secoisolariciresinol
Esol Class Soluble
Functional Groups CO, cO, cOC
Compound Name Secoisolariciresinol
Kingdom Organic compounds
Prediction Hob Swissadme 0.0
Exact Mass 362.173
Formal Charge 0.0
Monoisotopic Mass 362.173
Hydrogen Bond Acceptor Count 6.0
Molecular Weight 362.4
Gi Absorption True
Covalent Unit Count 1.0
Total Atom Stereocenter Count 2.0
Total Bond Stereocenter Count 0.0
Molecular Framework Aromatic homomonocyclic compounds
Lipinski Rule Of 5 True
Esol -3.422154861538462
Inchi 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
Smiles COC1=C(C=CC(=C1)C[C@@H](CO)[C@@H](CC2=CC(=C(C=C2)O)OC)CO)O
Nring 2.0
Np Classifier Biosynthetic Pathway Shikimates and Phenylpropanoids
Defined Bond Stereocenter Count 0.0
Egan Rule True
Taxonomy Direct Parent Dibenzylbutanediol lignans
Np Classifier Superclass Lignans

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