NP-MRD: Showing NP-Card for 4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one (NP0231185)

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Record Information

Version

2.0

Created at

2022-09-06 11:55:20 UTC

Updated at

2022-09-06 11:55:20 UTC

NP-MRD ID

NP0231185

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

Description

(-)-Arctiin belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. 4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one is found in Abeliophyllum distichum, Arctium lappa, Centaurea arenaria, Centaurea deflexa, Centaurea sclerolepis, Daphne feddei, Forsythia intermedia, Forsythia ovata, Onopordum illyricum, Plectocephalus americanus, Saussurea involucrata, Saussurea laniceps, Saussurea medusa, Saussurea salicifolia, Torreya nucifera, Trachelospermum asiaticum and Trachelospermum axillare. They include 1-aryltetralin lactones (-)-Arctiin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161522542D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004161522542D          

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   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    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  2  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  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  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  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  0  0  0  0
 18 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 31 34  2  0  0  0  0
 15 34  1  0  0  0  0
  6 35  1  0  0  0  0
 35 36  2  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0231185

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CC2COC(=O)C2CC2=CC=C(OC3OC(CO)C(O)C(O)C3O)C(OC)=C2)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O11/c1-33-18-6-4-14(10-20(18)34-2)8-16-13-36-26(32)17(16)9-15-5-7-19(21(11-15)35-3)37-27-25(31)24(30)23(29)22(12-28)38-27/h4-7,10-11,16-17,22-25,27-31H,8-9,12-13H2,1-3H3

> <INCHI_KEY>
XOJVHLIYNSOZOO-UHFFFAOYSA-N

> <FORMULA>
C27H34O11

> <MOLECULAR_WEIGHT>
534.558

> <EXACT_MASS>
534.210111915

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.41112197710589

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
1.71

> <JCHEM_LOGP>
1.169608473666667

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.196043729445432

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.20001489976324

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092354907191

> <JCHEM_POLAR_SURFACE_AREA>
153.37

> <JCHEM_REFRACTIVITY>
132.26110000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.755  -7.835   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.231  -9.300   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.771  -9.300   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.676 -10.546   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.247  -7.835   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.712  -7.359   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.032  -5.853   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.496  -5.377   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.817  -3.871   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -7.672  -2.840   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -7.992  -1.334   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -9.457  -0.858   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0     -10.601  -1.888   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0     -12.066  -1.413   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -13.210  -2.443   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -12.890  -3.949   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0     -12.386   0.094   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0     -13.851   0.570   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0     -11.242   1.124   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0     -11.562   2.631   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -9.777   0.648   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -8.633   1.679   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -6.207  -3.316   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -5.063  -2.286   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -3.598  -2.762   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.887  -4.822   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   35                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   34                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   20   30                                                  
CONECT   30   29                                                            
CONECT   31   18   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31   15                                                       
CONECT   35    6   36                                                       
CONECT   36   35    3   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₁₁

Average Mass

534.5580 Da

Monoisotopic Mass

534.21011 Da

IUPAC Name

4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

Traditional Name

4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CC2COC(=O)C2CC2=CC=C(OC3OC(CO)C(O)C(O)C3O)C(OC)=C2)C=C1OC

InChI Identifier

InChI=1S/C27H34O11/c1-33-18-6-4-14(10-20(18)34-2)8-16-13-36-26(32)17(16)9-15-5-7-19(21(11-15)35-3)37-27-25(31)24(30)23(29)22(12-28)38-27/h4-7,10-11,16-17,22-25,27-31H,8-9,12-13H2,1-3H3

InChI Key

XOJVHLIYNSOZOO-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
Abeliophyllum distichum	LOTUS Database	35616633
Arctium lappa	LOTUS Database	35616633
Centaurea arenaria	LOTUS Database	35616633
Centaurea deflexa	LOTUS Database	35616633
Centaurea sclerolepis	LOTUS Database	35616633
Daphne feddei	LOTUS Database	35616633
Forsythia intermedia	LOTUS Database	35616633
Forsythia ovata	LOTUS Database	35616633
Onopordum illyricum	LOTUS Database	35616633
Plectocephalus americanus	LOTUS Database	35616633
Saussurea involucrata	LOTUS Database	35616633
Saussurea laniceps	LOTUS Database	35616633
Saussurea medusa	LOTUS Database	35616633
Saussurea salicifolia	LOTUS Database	35616633
Torreya nucifera	LOTUS Database	35616633
Trachelospermum asiaticum	LOTUS Database	35616633
Trachelospermum axillare	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
Dibenzylbutyrolactone
Lignan lactone
Tetrahydrofuran lignan
9,9p-epoxylignan
Furanoid lignan
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Phenolic glycoside
Alkyl glycoside
O-glycosyl compound
Glycosyl compound
O-dimethoxybenzene
Dimethoxybenzene
Methoxybenzene
Phenol ether
Anisole
Phenoxy compound
Alkyl aryl ether
Fatty acyl
Oxane
Benzenoid
Monocyclic benzene moiety
Monosaccharide
Gamma butyrolactone
Oxolane
Lactone
Carboxylic acid ester
Secondary alcohol
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Polyol
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxygen compound
Organic oxide
Primary alcohol
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	1.71	ALOGPS
logP	1.17	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	153.37 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	132.26 m³·mol⁻¹	ChemAxon
Polarizability	54.41 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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

3660596

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one (NP0231185)

MOL for NP0231185 (4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

3D MOL for NP0231185 (4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

3D SDF for NP0231185 (4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

3D-SDF for NP0231185 (4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

PDB for NP0231185 (4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

3D PDB for NP0231185 (4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

SMILES for NP0231185 (4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

INCHI for NP0231185 (4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

Structure for NP0231185 (4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

3D Structure for NP0231185 (4-[(3,4-dimethoxyphenyl)methyl]-3-[(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)