NP-MRD: Showing NP-Card for (+)-5,5'-Dimethoxy-9-O-beta-D-glucopyranosyl lariciresinol (NP0081530)

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Record Information

Version

2.0

Created at

2022-04-29 02:32:08 UTC

Updated at

2022-04-29 02:32:08 UTC

NP-MRD ID

NP0081530

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-5,5'-Dimethoxy-9-O-beta-D-glucopyranosyl lariciresinol

Description

CHEMBL4461067 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. (+)-5,5'-Dimethoxy-9-O-beta-D-glucopyranosyl lariciresinol is found in Capparis flavicans and Baphicacanthus cusia . Based on a literature review very few articles have been published on CHEMBL4461067.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292204322D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292204322D          

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   -5.8114   -1.0614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5052   -3.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1696   -3.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3491   -4.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -4.8297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985   -5.4971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3190   -5.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6546   -4.6572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8039   -6.0783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4684   -6.8320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1630   -6.2508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8069   -4.9159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424   -5.6696    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12  2  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  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
 19 24  1  0  0  0  0
 24 25  1  1  0  0  0
 23 26  1  6  0  0  0
 22 27  1  1  0  0  0
 21 28  1  6  0  0  0
 28 29  1  0  0  0  0
 15 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 31 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 34 39  1  0  0  0  0
 33 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0081530

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C[C@H]2CO[C@@H]([C@H]2CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2=CC(OC)=C(O)C(OC)=C2)=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O13/c1-35-17-6-13(7-18(36-2)22(17)30)5-15-11-39-27(14-8-19(37-3)23(31)20(9-14)38-4)16(15)12-40-28-26(34)25(33)24(32)21(10-29)41-28/h6-9,15-16,21,24-34H,5,10-12H2,1-4H3/t15-,16-,21+,24+,25-,26+,27+,28+/m0/s1

> <INCHI_KEY>
HIFLTWHGASFARX-CIBVIZDISA-N

> <FORMULA>
C28H38O13

> <MOLECULAR_WEIGHT>
582.599

> <EXACT_MASS>
582.231241284

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
59.99948588632626

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(2S,3R,4R)-2-(4-hydroxy-3,5-dimethoxyphenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]oxolan-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
0.21913213799999953

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.829674870345666

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.1499412756234

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810834118486103

> <JCHEM_POLAR_SURFACE_AREA>
185.98999999999998

> <JCHEM_REFRACTIVITY>
142.53329999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{[(2S,3R,4R)-2-(4-hydroxy-3,5-dimethoxyphenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]oxolan-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  C   UNK     0       0.199  -0.115   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.134  -0.885   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.468  -0.115   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      -1.134   2.195   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.199   1.425   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.533   2.195   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.533   3.735   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.134   3.735   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -3.802   2.195   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.802   3.735   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.134  -2.425   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.111  -3.330   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.364  -4.795   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.904  -4.795   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.380  -3.330   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.845  -2.854   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.165  -1.348   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -5.630  -0.872   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -6.774  -1.903   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -8.239  -1.427   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.559   0.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -7.415   1.110   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.950   0.634   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.806   1.665   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -7.735   2.617   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0     -10.024   0.556   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -9.383  -2.457   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0     -10.848  -1.981   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.810  -6.041   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.183  -7.448   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.652  -7.609   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.025  -9.015   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.931 -10.261   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.462 -10.100   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -3.088  -8.693   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -3.367 -11.346   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -2.741 -12.753   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -0.304 -11.668   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       1.506  -9.176   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       2.133 -10.583   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5                                                            
CONECT   10    4   11                                                       
CONECT   11   10                                                            
CONECT   12    2   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   30                                                  
CONECT   16   15   12   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   19   25                                                  
CONECT   25   24                                                            
CONECT   26   23                                                            
CONECT   27   22                                                            
CONECT   28   21   29                                                       
CONECT   29   28                                                            
CONECT   30   15   31                                                       
CONECT   31   30   32   36                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   40                                                  
CONECT   34   33   35   39                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35   31                                                       
CONECT   37   35   38                                                       
CONECT   38   37                                                            
CONECT   39   34                                                            
CONECT   40   33   41                                                       
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₈O₁₃

Average Mass

582.5990 Da

Monoisotopic Mass

582.23124 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[(2S,3R,4R)-2-(4-hydroxy-3,5-dimethoxyphenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]oxolan-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4S,5S,6R)-2-{[(2S,3R,4R)-2-(4-hydroxy-3,5-dimethoxyphenyl)-4-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]oxolan-3-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=CC(C[C@H]2CO[C@@H]([C@H]2CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2=CC(OC)=C(O)C(OC)=C2)=CC(OC)=C1O

InChI Identifier

InChI=1S/C28H38O13/c1-35-17-6-13(7-18(36-2)22(17)30)5-15-11-39-27(14-8-19(37-3)23(31)20(9-14)38-4)16(15)12-40-28-26(34)25(33)24(32)21(10-29)41-28/h6-9,15-16,21,24-34H,5,10-12H2,1-4H3/t15-,16-,21+,24+,25-,26+,27+,28+/m0/s1

InChI Key

HIFLTWHGASFARX-CIBVIZDISA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Capparis flavicans	Plant	KNApSAcK
Strobilanthes cusia	-	KNApSAcK

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
Tetrahydrofuran lignan
7,9p-epoxylignan
Furanoid lignan
Glycosyl compound
O-glycosyl compound
Dimethoxybenzene
M-dimethoxybenzene
Methoxyphenol
Methoxybenzene
Anisole
Phenoxy compound
Phenol ether
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Dialkyl ether
Ether
Acetal
Polyol
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
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	0.66	ALOGPS
logP	0.22	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.15	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	185.99 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	142.53 m³·mol⁻¹	ChemAxon
Polarizability	60 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

155528232

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-5,5'-Dimethoxy-9-O-beta-D-glucopyranosyl lariciresinol (NP0081530)

MOL for NP0081530 ((+)-5,5'-Dimethoxy-9-O-beta-D-glucopyranosyl lariciresinol)

3D MOL for NP0081530 ((+)-5,5'-Dimethoxy-9-O-beta-D-glucopyranosyl lariciresinol)

3D SDF for NP0081530 ((+)-5,5'-Dimethoxy-9-O-beta-D-glucopyranosyl lariciresinol)

3D-SDF for NP0081530 ((+)-5,5'-Dimethoxy-9-O-beta-D-glucopyranosyl lariciresinol)

PDB for NP0081530 ((+)-5,5'-Dimethoxy-9-O-beta-D-glucopyranosyl lariciresinol)

3D PDB for NP0081530 ((+)-5,5'-Dimethoxy-9-O-beta-D-glucopyranosyl lariciresinol)

SMILES for NP0081530 ((+)-5,5'-Dimethoxy-9-O-beta-D-glucopyranosyl lariciresinol)

INCHI for NP0081530 ((+)-5,5'-Dimethoxy-9-O-beta-D-glucopyranosyl lariciresinol)

Structure for NP0081530 ((+)-5,5'-Dimethoxy-9-O-beta-D-glucopyranosyl lariciresinol)

3D Structure for NP0081530 ((+)-5,5'-Dimethoxy-9-O-beta-D-glucopyranosyl lariciresinol)