NP-MRD: Showing NP-Card for (4s)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one (NP0163586)

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Record Information

Version

2.0

Created at

2022-09-02 22:16:33 UTC

Updated at

2022-09-02 22:16:33 UTC

NP-MRD ID

NP0163586

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one

Description

Enterolactone, also known as BHMDF or 2,3-BHBB, belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. (4s)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one is found in Linum usitatissimum. (4s)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one was first documented in 2022 (PMID: 35633575). Based on a literature review a small amount of articles have been published on Enterolactone (PMID: 35914449) (PMID: 35757242) (PMID: 35745107) (PMID: 35532015).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    2.7428   -2.6349    1.4607 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5962   -2.2052    1.1376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771   -2.8818    0.3330 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6045   -2.2415    0.4558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1668   -0.8009    0.6023 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2093    0.0601    1.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4867    0.1036    0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4685   -0.8229    0.7913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6856   -0.8277    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9584    0.1049   -0.8531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9832    1.0366   -1.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2457    1.9768   -2.1141 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7639    1.0347   -0.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985   -0.9430    1.5244 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8908    0.2522    1.5734 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4988    0.6267    0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8695    1.4914   -0.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4559    1.8423   -1.7924 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6835    1.3268   -2.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3274    0.4603   -1.2873 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5617   -0.0336   -1.6843 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7216    0.1290   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1258   -2.6239    1.3607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2223   -2.4135   -0.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1080   -0.4482   -0.4083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3435   -0.2884    2.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7608    1.0820    1.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2719   -1.5728    1.5634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4550   -1.5560    0.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9112    0.1179   -1.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6762    2.8427   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9921    1.7699   -0.6848 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -1.0770    2.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6752    0.0331    2.3573 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2930    1.0864    2.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9060    1.9336   -0.3696 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9758    2.5184   -2.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1307    1.6058   -3.0893 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3996    0.4853   -1.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2586   -0.5492    0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 13  2  0
 13  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 14  5  1  0
 22 16  1  0
 12 31  1  0
 13 32  1  0
  6 26  1  0
  6 27  1  0
  5 25  1  6
  4 23  1  0
  4 24  1  0
 14 33  1  1
 15 34  1  0
 15 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 21 39  1  0
 22 40  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
M  END


  Mrv1652309032200162D          

 22 24  0  0  1  0            999 V2000
    2.0367   -0.4741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367   -1.2991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7041   -1.7840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -2.5687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6242   -2.5687    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1393   -3.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4748   -3.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2953   -4.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6309   -4.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1460   -5.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3255   -5.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8406   -6.0783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9899   -4.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3693   -1.7840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4131   -0.7221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3715   -0.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5430    0.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0701    0.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8547    0.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4678    1.1889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0262   -0.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  7 13  1  0  0  0  0
  5 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 16 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0163586

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(C[C@@H]2COC(=O)C2CC2=CC=CC(O)=C2)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2/t14-,17?/m1/s1

> <INCHI_KEY>
HVDGDHBAMCBBLR-XPCCGILXSA-N

> <FORMULA>
C18H18O4

> <MOLECULAR_WEIGHT>
298.338

> <EXACT_MASS>
298.12050906

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
30.922298487506243

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
3.607125042333333

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.765099955610825

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.163039070788626

> <JCHEM_PKA_STRONGEST_BASIC>
-5.9640436366683405

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
82.708

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  O   UNK     0       3.802  -0.885   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.048  -3.330   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.572  -4.795   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.032  -4.795   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.127  -6.041   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.753  -7.448   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.285  -7.609   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.911  -9.015   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.006 -10.261   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.474 -10.100   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.569 -11.346   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.848  -8.693   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.091  -2.854   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.771  -1.348   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.693  -0.872   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.014   0.634   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.131   1.665   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.595   1.189   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.740   2.219   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.916  -0.317   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7                                                       
CONECT   14    5    2   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-(+-)-isomer	MeSH
BHMDF	MeSH
2,3-BHBB	MeSH
2,3-Bis(3'-hydroxybenzyl)butyrolactone	MeSH
3,4-Bis((3-hydroxyphenyl)methyl)dihydro-2-(3H)-furanone	MeSH
trans-2,3-Bis(3-hydroxybenzyl)-gamma-butyrolactone	MeSH
2,3-Bis(3'-hydroxybenzyl)butyrolactone, (trans)-isomer	MeSH
HPMF	MeSH

Chemical Formula

C₁₈H₁₈O₄

Average Mass

298.3380 Da

Monoisotopic Mass

298.12051 Da

IUPAC Name

(4S)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one

Traditional Name

(4S)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

OC1=CC(C[C@@H]2COC(=O)C2CC2=CC=CC(O)=C2)=CC=C1

InChI Identifier

InChI=1S/C18H18O4/c19-15-5-1-3-12(8-15)7-14-11-22-18(21)17(14)10-13-4-2-6-16(20)9-13/h1-6,8-9,14,17,19-20H,7,10-11H2/t14-,17?/m1/s1

InChI Key

HVDGDHBAMCBBLR-XPCCGILXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Linum usitatissimum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

Dibenzylbutyrolactone lignans

Alternative Parents

Substituents

Dibenzylbutyrolactone
Lignan lactone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Gamma butyrolactone
Benzenoid
Oxolane
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.2	ALOGPS
logP	3.61	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.16	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.71 m³·mol⁻¹	ChemAxon
Polarizability	30.92 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00000703

Chemspider ID

21466929

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Enterolactone

METLIN ID

Not Available

PubChem Compound

71684354

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hamdi T, Gouissem I: Potential effect of Enterolactone and Raloxifene in reversing osteoarthritis markers in cultured human articular chondrocytes. ARP Rheumatol. 2022 Jan-Mar;1(1):30-41. [PubMed:35633575 ]
Yu L, Xu Q, Wang P, Luo J, Zheng Z, Zhou J, Zhang L, Sun L, Zuo D: Secoisolariciresinol diglucoside-derived metabolite, enterolactone, attenuates atopic dermatitis by suppressing Th2 immune response. Int Immunopharmacol. 2022 Oct;111:109039. doi: 10.1016/j.intimp.2022.109039. Epub 2022 Jul 29. [PubMed:35914449 ]
Castellano-Escuder P, Gonzalez-Dominguez R, Vaillant MF, Casas-Agustench P, Hidalgo-Liberona N, Estanyol-Torres N, Wilson T, Beckmann M, Lloyd AJ, Oberli M, Moinard C, Pison C, Borel JC, Joyeux-Faure M, Sicard M, Artemova S, Terrisse H, Dancer P, Draper J, Sanchez-Pla A, Andres-Lacueva C: Assessing Adherence to Healthy Dietary Habits Through the Urinary Food Metabolome: Results From a European Two-Center Study. Front Nutr. 2022 Jun 9;9:880770. doi: 10.3389/fnut.2022.880770. eCollection 2022. [PubMed:35757242 ]
Mullens DA, Ivanov I, Hullar MAJ, Randolph TW, Lampe JW, Chapkin RS: Personalized Nutrition Using Microbial Metabolite Phenotype to Stratify Participants and Non-Invasive Host Exfoliomics Reveal the Effects of Flaxseed Lignan Supplementation in a Placebo-Controlled Crossover Trial. Nutrients. 2022 Jun 8;14(12):2377. doi: 10.3390/nu14122377. [PubMed:35745107 ]
Tse TJ, Guo Y, Shim YY, Purdy SK, Kim JH, Cho JY, Alcorn J, Reaney MJT: Availability of bioactive flax lignan from foods and supplements. Crit Rev Food Sci Nutr. 2023;63(29):9843-9858. doi: 10.1080/10408398.2022.2072807. Epub 2022 May 9. [PubMed:35532015 ]
LOTUS database [Link]

Showing NP-Card for (4s)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one (NP0163586)

MOL for NP0163586 ((4s)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one)

3D MOL for NP0163586 ((4s)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one)

3D SDF for NP0163586 ((4s)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one)

3D-SDF for NP0163586 ((4s)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one)

PDB for NP0163586 ((4s)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one)

3D PDB for NP0163586 ((4s)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one)

SMILES for NP0163586 ((4s)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one)

INCHI for NP0163586 ((4s)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one)

Structure for NP0163586 ((4s)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one)

3D Structure for NP0163586 ((4s)-3,4-bis[(3-hydroxyphenyl)methyl]oxolan-2-one)