NP-MRD: Showing NP-Card for 3-({3-methoxy-4,5-bis[(trimethylsilyl)oxy]phenyl}methyl)-4-({3-methoxy-4-[(trimethylsilyl)oxy]phenyl}methyl)oxolan-2-one (NP0241908)

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Record Information

Version

2.0

Created at

2022-09-07 02:06:01 UTC

Updated at

2022-09-07 02:06:01 UTC

NP-MRD ID

NP0241908

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-({3-methoxy-4,5-bis[(trimethylsilyl)oxy]phenyl}methyl)-4-({3-methoxy-4-[(trimethylsilyl)oxy]phenyl}methyl)oxolan-2-one

Description

Thujaplicatin belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. 3-({3-methoxy-4,5-bis[(trimethylsilyl)oxy]phenyl}methyl)-4-({3-methoxy-4-[(trimethylsilyl)oxy]phenyl}methyl)oxolan-2-one is found in Juniperus phoenicea. 3-({3-methoxy-4,5-bis[(trimethylsilyl)oxy]phenyl}methyl)-4-({3-methoxy-4-[(trimethylsilyl)oxy]phenyl}methyl)oxolan-2-one was first documented in 2003 (PMID: 12956064). Based on a literature review a small amount of articles have been published on Thujaplicatin (PMID: 18569716) (PMID: 17555638).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072204062D          

 39 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072204062D          

 39 41  0  0  0  0            999 V2000
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   -4.5122   -3.7372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2968   -3.4823    0.0000 Si  0  0  0  0  0  0  0  0  0  0  0  0
   -6.0814   -3.2273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5518   -4.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0419   -2.6977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0706   -2.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8553   -2.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0268   -1.3163    0.0000 Si  0  0  0  0  0  0  0  0  0  0  0  0
   -4.2198   -1.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8338   -1.4878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1983   -0.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4575   -1.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367   -0.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4656    1.1759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1801    0.7634    0.0000 Si  0  0  0  0  0  0  0  0  0  0  0  0
   -4.8946    0.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5926    1.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7676    0.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 25 31  2  0  0  0  0
 14 31  1  0  0  0  0
  5 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
  3 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0241908

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CC2COC(=O)C2CC2=CC(OC)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)=CC=C1O[Si](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H46O7Si3/c1-31-25-16-20(12-13-24(25)34-37(3,4)5)14-22-19-33-29(30)23(22)15-21-17-26(32-2)28(36-39(9,10)11)27(18-21)35-38(6,7)8/h12-13,16-18,22-23H,14-15,19H2,1-11H3

> <INCHI_KEY>
FHYCUWIIEMRFFI-UHFFFAOYSA-N

> <FORMULA>
C29H46O7Si3

> <MOLECULAR_WEIGHT>
590.935

> <EXACT_MASS>
590.255133426

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
62.39671531558636

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-({3-methoxy-4,5-bis[(trimethylsilyl)oxy]phenyl}methyl)-4-({3-methoxy-4-[(trimethylsilyl)oxy]phenyl}methyl)oxolan-2-one

> <JCHEM_LOGP>
7.308600000000001

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1199330727622705

> <JCHEM_POLAR_SURFACE_AREA>
72.45000000000002

> <JCHEM_REFRACTIVITY>
145.99300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-({3-methoxy-4,5-bis[(trimethylsilyl)oxy]phenyl}methyl)-4-({3-methoxy-4-[(trimethylsilyl)oxy]phenyl}methyl)oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.136   4.505   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.802   3.735   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.802   2.195   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.468   1.425   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.468  -0.115   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.134  -0.885   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.134  -2.425   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.111  -3.330   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -0.364  -4.795   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.904  -4.795   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.810  -6.041   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.380  -3.330   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.845  -2.854   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.989  -3.885   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.669  -5.391   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.814  -6.422   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.494  -7.928   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -6.638  -8.958   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -7.278  -5.946   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -8.423  -6.976   0.000  0.00  0.00           O+0
HETATM   21 Si   UNK     0      -9.887  -6.500   0.000  0.00  0.00          Si+0
HETATM   22  C   UNK     0     -11.352  -6.024   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -10.363  -7.965   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -9.412  -5.036   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.599  -4.439   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -9.063  -3.963   0.000  0.00  0.00           O+0
HETATM   27 Si   UNK     0      -9.383  -2.457   0.000  0.00  0.00          Si+0
HETATM   28  C   UNK     0      -7.877  -2.137   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -10.890  -2.777   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -9.704  -0.951   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -6.454  -3.409   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.802  -0.885   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.136  -0.115   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.136   1.425   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -6.469   2.195   0.000  0.00  0.00           O+0
HETATM   36 Si   UNK     0      -7.803   1.425   0.000  0.00  0.00          Si+0
HETATM   37  C   UNK     0      -9.137   0.655   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -8.573   2.759   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -7.033   0.091   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   31                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
CONECT   25   19   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   25   14                                                       
CONECT   32    5   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33    3   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₆O₇Si₃

Average Mass

590.9350 Da

Monoisotopic Mass

590.25513 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC(CC2COC(=O)C2CC2=CC(OC)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)=CC=C1O[Si](C)(C)C

InChI Identifier

InChI=1S/C29H46O7Si3/c1-31-25-16-20(12-13-24(25)34-37(3,4)5)14-22-19-33-29(30)23(22)15-21-17-26(32-2)28(36-39(9,10)11)27(18-21)35-38(6,7)8/h12-13,16-18,22-23H,14-15,19H2,1-11H3

InChI Key

FHYCUWIIEMRFFI-UHFFFAOYSA-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
Juniperus phoenicea	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
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
Alkyl aryl ether
Benzenoid
Gamma butyrolactone
Monocyclic benzene moiety
Trialkylheterosilane
Tetrahydrofuran
Lactone
Carboxylic acid ester
Organoheterosilane
Oxacycle
Organic metalloid salt
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Organosilicon compound
Organooxygen compound
Carbonyl group
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122211995

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Sakakibara N, Suzuki S, Umezawa T, Shimada M: Biosynthesis of yatein in Anthriscus sylvestris. Org Biomol Chem. 2003 Jul 21;1(14):2474-85. doi: 10.1039/b304411d. [PubMed:12956064 ]
Lin RJ, Chen CY, Lo WL: Cytotoxic activity of Ipomoea cairica. Nat Prod Res. 2008 Jun 15;22(9):747-53. doi: 10.1080/14786410701628739. [PubMed:18569716 ]
Daniels CR, Russell JH: Analysis of western redcedar (Thuja plicata Donn) heartwood components by HPLC as a possible screening tool for trees with enhanced natural durability. J Chromatogr Sci. 2007 May-Jun;45(5):281-5. doi: 10.1093/chromsci/45.5.281. [PubMed:17555638 ]
LOTUS database [Link]

Showing NP-Card for 3-({3-methoxy-4,5-bis[(trimethylsilyl)oxy]phenyl}methyl)-4-({3-methoxy-4-[(trimethylsilyl)oxy]phenyl}methyl)oxolan-2-one (NP0241908)

MOL for NP0241908 (3-({3-methoxy-4,5-bis[(trimethylsilyl)oxy]phenyl}methyl)-4-({3-methoxy-4-[(trimethylsilyl)oxy]phenyl}methyl)oxolan-2-one)

3D MOL for NP0241908 (3-({3-methoxy-4,5-bis[(trimethylsilyl)oxy]phenyl}methyl)-4-({3-methoxy-4-[(trimethylsilyl)oxy]phenyl}methyl)oxolan-2-one)

3D SDF for NP0241908 (3-({3-methoxy-4,5-bis[(trimethylsilyl)oxy]phenyl}methyl)-4-({3-methoxy-4-[(trimethylsilyl)oxy]phenyl}methyl)oxolan-2-one)

3D-SDF for NP0241908 (3-({3-methoxy-4,5-bis[(trimethylsilyl)oxy]phenyl}methyl)-4-({3-methoxy-4-[(trimethylsilyl)oxy]phenyl}methyl)oxolan-2-one)

PDB for NP0241908 (3-({3-methoxy-4,5-bis[(trimethylsilyl)oxy]phenyl}methyl)-4-({3-methoxy-4-[(trimethylsilyl)oxy]phenyl}methyl)oxolan-2-one)

3D PDB for NP0241908 (3-({3-methoxy-4,5-bis[(trimethylsilyl)oxy]phenyl}methyl)-4-({3-methoxy-4-[(trimethylsilyl)oxy]phenyl}methyl)oxolan-2-one)

SMILES for NP0241908 (3-({3-methoxy-4,5-bis[(trimethylsilyl)oxy]phenyl}methyl)-4-({3-methoxy-4-[(trimethylsilyl)oxy]phenyl}methyl)oxolan-2-one)

INCHI for NP0241908 (3-({3-methoxy-4,5-bis[(trimethylsilyl)oxy]phenyl}methyl)-4-({3-methoxy-4-[(trimethylsilyl)oxy]phenyl}methyl)oxolan-2-one)

Structure for NP0241908 (3-({3-methoxy-4,5-bis[(trimethylsilyl)oxy]phenyl}methyl)-4-({3-methoxy-4-[(trimethylsilyl)oxy]phenyl}methyl)oxolan-2-one)

3D Structure for NP0241908 (3-({3-methoxy-4,5-bis[(trimethylsilyl)oxy]phenyl}methyl)-4-({3-methoxy-4-[(trimethylsilyl)oxy]phenyl}methyl)oxolan-2-one)