NP-MRD: Showing NP-Card for (−)-matairesinol (NP0350972)

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Record Information

Version

2.0

Created at

2025-04-24 04:45:12 UTC

Updated at

2025-05-12 16:32:47 UTC

NP-MRD ID

NP0350972

Natural Product DOI

https://doi.org/10.57994/3959

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(−)-matairesinol

Description

(-)-Matairesinol, also known as artigenin congener, belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety (-)-Matairesinol is an extremely weak basic (essentially neutral) compound (based on its pKa). (−)-matairesinol was first documented in 2005 (PMID: 15653677). A lignan that is gamma-butyrolactone in which the 3 and 4 positions are substituted by 4-hydroxy-3-methoxybenzyl groups (the 3R,4R-diastereomer) (PMID: 18803219) (PMID: 19935713) (PMID: 20734328) (PMID: 21315909) (PMID: 40241524).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309272007272D          

 26 28  0  0  0  0            999 V2000
10001.1293 9998.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.557510000.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.706410001.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.985710000.1620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8698 9998.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.442010000.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.155910001.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.014210000.1620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5629 9999.9514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.011010000.1901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3436 9999.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5985 9998.9205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.4235 9998.9205    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.6784 9999.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.441910000.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7275 9999.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7275 9998.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4419 9998.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1564 9998.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1564 9999.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2727 9999.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.558310000.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8437 9999.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8437 9998.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5582 9998.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2727 9998.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  6  7  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 13  1  1  6  0  0  0
 12  5  1  1  0  0  0
 11  9  2  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 15  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 21  1  0  0  0  0
  1 24  1  0  0  0  0
 22  2  1  0  0  0  0
 21  4  1  0  0  0  0
  5 19  1  0  0  0  0
 15  6  1  0  0  0  0
 16  8  1  0  0  0  0
M  END


  Mrv1652309272007272D          

 26 28  0  0  0  0            999 V2000
10001.1293 9998.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.557510000.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.706410001.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.985710000.1620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8698 9998.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.442010000.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.155910001.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.014210000.1620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5629 9999.9514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.011010000.1901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3436 9999.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5985 9998.9205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.4235 9998.9205    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.6784 9999.7051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.441910000.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7275 9999.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7275 9998.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4419 9998.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1564 9998.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1564 9999.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2727 9999.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.558310000.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8437 9999.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8437 9998.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.5582 9998.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2727 9998.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  6  7  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 13  1  1  6  0  0  0
 12  5  1  1  0  0  0
 11  9  2  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 15  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 21  1  0  0  0  0
  1 24  1  0  0  0  0
 22  2  1  0  0  0  0
 21  4  1  0  0  0  0
  5 19  1  0  0  0  0
 15  6  1  0  0  0  0
 16  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0350972

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(OC)=C(O)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m0/s1

> <INCHI_KEY>
MATGKVZWFZHCLI-LSDHHAIUSA-N

> <FORMULA>
C20H22O6

> <MOLECULAR_WEIGHT>
358.3851

> <EXACT_MASS>
358.141638436

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
36.8600588964603

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
3.2917825110000005

> <ALOGPS_LOGS>
-4.47

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.246760875760991

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.644700805894656

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5896887507776425

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
95.6344

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
matairesinol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8668.7758663.891   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8671.4418668.508   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8669.8528669.423   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8674.1078666.969   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8664.5578663.891   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8661.8928668.508   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8663.2248669.273   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0    8659.2278666.969   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8663.9848666.576   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8666.6878667.022   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8665.4418666.116   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.9178664.652   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8667.4578664.652   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8667.9338666.116   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8661.8928666.969   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8660.5588666.199   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8660.5588664.659   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8661.8928663.889   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8663.2258664.659   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8663.2258666.199   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8672.7768666.199   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8671.4428666.969   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8670.1088666.199   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8670.1088664.659   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8671.4428663.889   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8672.7768664.659   0.000  0.00  0.00           C+0
CONECT    1   13   24                                                       
CONECT    2    3   22                                                       
CONECT    3    2                                                            
CONECT    4   21                                                            
CONECT    5   12   19                                                       
CONECT    6    7   15                                                       
CONECT    7    6                                                            
CONECT    8   16                                                            
CONECT    9   11                                                            
CONECT   10   11   14                                                       
CONECT   11   12   10    9                                                  
CONECT   12   11   13    5                                                  
CONECT   13   12   14    1                                                  
CONECT   14   13   10                                                       
CONECT   15   16   20    6                                                  
CONECT   16   15   17    8                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20    5                                                  
CONECT   20   19   15                                                       
CONECT   21   22   26    4                                                  
CONECT   22   21   23    2                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25    1                                                  
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
3R,4R-Bis((4-hydroxy-3-methoxyphenyl)methyl)dihydro-2(3H)-furanone	ChEBI
Artigenin congener	ChEBI
Matairesinol	ChEBI
(3R,4R)-3,4-Bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one	Kegg
(8R,8'r)-(-)-Matairesinol	HMDB
Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-(3R,4R)-2(3H)-furanone	HMDB
Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-(3R-trans)-2(3H)-furanone	HMDB
Matai-resinol	HMDB
(-)-Matairesinol	KEGG
(3R,4R)-Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone	HMDB
(8R,8’R)-(-)-Matairesinol	HMDB
Dihydro-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone	HMDB
Dihydro-3,4-divanillyl-2(3H)-furanone	PhytoBank

Chemical Formula

C₂₀H₂₂O₆

Average Mass

358.3851 Da

Monoisotopic Mass

358.14164 Da

IUPAC Name

(3R,4R)-3,4-bis[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

Traditional Name

matairesinol

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(C[C@H]2COC(=O)[C@@H]2CC2=CC(OC)=C(O)C=C2)=C1

InChI Identifier

InChI=1S/C20H22O6/c1-24-18-9-12(3-5-16(18)21)7-14-11-26-20(23)15(14)8-13-4-6-17(22)19(10-13)25-2/h3-6,9-10,14-15,21-22H,7-8,11H2,1-2H3/t14-,15+/m0/s1

InChI Key

MATGKVZWFZHCLI-LSDHHAIUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D_DEPT NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	dr.yknalli@iiim.res.in	CSIR-Indian Institute of Integrative Medicine	Yedukondalu Nalli	2025-04-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)	dr.yknalli@iiim.res.in	CSIR-Indian Institute of Integrative Medicine	Yedukondalu Nalli	2025-04-24	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	dr.yknalli@iiim.res.in	CSIR-Indian Institute of Integrative Medicine	Yedukondalu Nalli	2025-04-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	dr.yknalli@iiim.res.in	CSIR-Indian Institute of Integrative Medicine	Yedukondalu Nalli	2025-04-24	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	dr.yknalli@iiim.res.in	CSIR-Indian Institute of Integrative Medicine	Yedukondalu Nalli	2025-04-24	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	dr.yknalli@iiim.res.in	CSIR-Indian Institute of Integrative Medicine	Yedukondalu Nalli	2025-04-24	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CD3OD, experimental)	dr.yknalli@iiim.res.in	CSIR-Indian Institute of Integrative Medicine	Yedukondalu Nalli	2025-04-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD3OD, experimental)	dr.yknalli@iiim.res.in	CSIR-Indian Institute of Integrative Medicine	Yedukondalu Nalli	2025-04-24	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Himalaiella heteromalla		Not Available

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
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

polyphenol (CHEBI:6698 )
gamma-lactone (CHEBI:6698 )
lignan (CHEBI:6698 )
Lignans (C10682 )

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	2.79	ALOGPS
logP	3.29	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.64	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	95.63 m³·mol⁻¹	ChemAxon
Polarizability	36.86 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0035698

DrugBank ID

DB04200

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Matairesinol

METLIN ID

Not Available

PubChem Compound

119205

PDB ID

Not Available

ChEBI ID

6698

Good Scents ID

Not Available

References

General References

Muller U, Mrestani Y, Neubert R, Drager B: Chiral separation of the plant lignan matairesinol by capillary electrophoresis. Electrophoresis. 2008 Sep;29(17):3582-7. doi: 10.1002/elps.200700800. [PubMed:18803219 ]
Youn B, Moinuddin SG, Davin LB, Lewis NG, Kang C: Crystal structures of apo-form and binary/ternary complexes of Podophyllum secoisolariciresinol dehydrogenase, an enzyme involved in formation of health-protecting and plant defense lignans. J Biol Chem. 2005 Apr 1;280(13):12917-26. doi: 10.1074/jbc.M413266200. Epub 2005 Jan 13. [PubMed:15653677 ]
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DOI: 10.1080/14786419.2025.2491122
PMID: 40241524

Showing NP-Card for (−)-matairesinol (NP0350972)

MOL for NP0350972 ((−)-matairesinol)

3D MOL for NP0350972 ((−)-matairesinol)

3D SDF for NP0350972 ((−)-matairesinol)

3D-SDF for NP0350972 ((−)-matairesinol)

PDB for NP0350972 ((−)-matairesinol)

3D PDB for NP0350972 ((−)-matairesinol)

SMILES for NP0350972 ((−)-matairesinol)

INCHI for NP0350972 ((−)-matairesinol)

Structure for NP0350972 ((−)-matairesinol)

3D Structure for NP0350972 ((−)-matairesinol)