NP-MRD: Showing NP-Card for 4-O-(3-O-methyl-beta-D-glucopyranosyl)-diphyllin (NP0074607)

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Record Information

Version

2.0

Created at

2022-04-28 19:54:14 UTC

Updated at

2022-04-28 19:54:15 UTC

NP-MRD ID

NP0074607

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-O-(3-O-methyl-beta-D-glucopyranosyl)-diphyllin

Description

4-(3-O-Methyl-beta-D-glucopyranosyloxy)-6,7-dimethoxy-9-(1,3-benzodioxole-5-yl)naphtho[2,3-c]furan-1(3H)-one 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. 4-O-(3-O-methyl-beta-D-glucopyranosyl)-diphyllin is found in Cleistanthus collinus. Based on a literature review very few articles have been published on 4-(3-O-Methyl-beta-D-glucopyranosyloxy)-6,7-dimethoxy-9-(1,3-benzodioxole-5-yl)naphtho[2,3-c]furan-1(3H)-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221542D          

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M  END

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  Mrv1652304282221542D          

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  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  1  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  1  0  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 12 15  1  1  0  0  0
 15 16  1  0  0  0  0
 11 17  1  6  0  0  0
 10 18  1  1  0  0  0
 18 19  1  0  0  0  0
  5 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
  4 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  0  0  0  0
  3 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 28 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 30 36  1  0  0  0  0
  2 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
  1 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074607

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1[C@H](O)[C@@H](CO)O[C@@H](OC2=C3C=C(OC)C(OC)=CC3=C(C3=C2COC3=O)C2=CC3=C(OCO3)C=C2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H28O12/c1-33-17-7-13-14(8-18(17)34-2)25(40-28-24(31)26(35-3)23(30)20(9-29)39-28)15-10-36-27(32)22(15)21(13)12-4-5-16-19(6-12)38-11-37-16/h4-8,20,23-24,26,28-31H,9-11H2,1-3H3/t20-,23-,24-,26+,28+/m1/s1

> <INCHI_KEY>
IJNZCBYSQOHZML-GQBVEXEASA-N

> <FORMULA>
C28H28O12

> <MOLECULAR_WEIGHT>
556.52

> <EXACT_MASS>
556.158076342

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
55.4314441984453

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-(2H-1,3-benzodioxol-5-yl)-4-{[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy}-6,7-dimethoxy-1H,3H-naphtho[2,3-c]furan-1-one

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
1.5440362249999993

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.04563832314015

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.241369171893592

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810982935236208

> <JCHEM_POLAR_SURFACE_AREA>
151.60000000000002

> <JCHEM_REFRACTIVITY>
135.7941

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(2H-1,3-benzodioxol-5-yl)-4-{[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy}-6,7-dimethoxy-3H-naphtho[2,3-c]furan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      14.123  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.789  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.455  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.455  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.789  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.123  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      15.456  -7.700   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      15.456  -9.240   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      14.123 -10.010   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      14.123 -11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.456 -12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.790 -11.550   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.790 -10.010   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      18.124  -9.240   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      18.124 -12.320   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      18.124 -13.860   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      15.456 -13.860   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.789 -12.320   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      12.789 -13.860   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      12.789  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.455 -10.010   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.122  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.122  -7.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.788 -10.010   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.454  -9.240   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.455 -11.550   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.122 -12.320   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.122  -4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.788  -5.390   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.454  -4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.454  -3.080   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.788  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.122  -3.080   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.990  -2.604   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.085  -3.850   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.990  -5.096   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      13.109  -3.114   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      12.079  -1.969   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      14.641  -2.953   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      15.267  -4.360   0.000  0.00  0.00           C+0
CONECT    1    2    6   40                                                  
CONECT    2    1    3   37                                                  
CONECT    3    2    4   28                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6   20                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12   17                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15                                                            
CONECT   17   11                                                            
CONECT   18   10   19                                                       
CONECT   19   18                                                            
CONECT   20    5   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22    4                                                       
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   21   27                                                       
CONECT   27   26                                                            
CONECT   28    3   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   36                                                  
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32   28                                                       
CONECT   34   31   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   30                                                       
CONECT   37    2   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39    1                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
4-(3-O-Methyl-b-D-glucopyranosyloxy)-6,7-dimethoxy-9-(1,3-benzodioxole-5-yl)naphtho[2,3-c]furan-1(3H)-one	Generator
4-(3-O-Methyl-β-D-glucopyranosyloxy)-6,7-dimethoxy-9-(1,3-benzodioxole-5-yl)naphtho[2,3-c]furan-1(3H)-one	Generator

Chemical Formula

C₂₈H₂₈O₁₂

Average Mass

556.5200 Da

Monoisotopic Mass

556.15808 Da

IUPAC Name

9-(2H-1,3-benzodioxol-5-yl)-4-{[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy}-6,7-dimethoxy-1H,3H-naphtho[2,3-c]furan-1-one

Traditional Name

9-(2H-1,3-benzodioxol-5-yl)-4-{[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-methoxyoxan-2-yl]oxy}-6,7-dimethoxy-3H-naphtho[2,3-c]furan-1-one

CAS Registry Number

Not Available

SMILES

CO[C@H]1[C@H](O)[C@@H](CO)O[C@@H](OC2=C3C=C(OC)C(OC)=CC3=C(C3=C2COC3=O)C2=CC3=C(OCO3)C=C2)[C@@H]1O

InChI Identifier

InChI=1S/C28H28O12/c1-33-17-7-13-14(8-18(17)34-2)25(40-28-24(31)26(35-3)23(30)20(9-29)39-28)15-10-36-27(32)22(15)21(13)12-4-5-16-19(6-12)38-11-37-16/h4-8,20,23-24,26,28-31H,9-11H2,1-3H3/t20-,23-,24-,26+,28+/m1/s1

InChI Key

IJNZCBYSQOHZML-GQBVEXEASA-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
Cleistanthus collinus	Plant	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
Arylnaphthalene lignan skeleton
Lignan lactone
Phenolic glycoside
Naphthofuran
Glycosyl compound
O-glycosyl compound
Isobenzofuranone
Naphthalene
Phthalide
Isocoumaran
Benzodioxole
Anisole
Alkyl aryl ether
Benzenoid
Monosaccharide
Oxane
Carboxylic acid ester
Lactone
Secondary alcohol
Acetal
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Primary alcohol
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.65	ALOGPS
logP	1.54	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	12.24	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	151.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	135.79 m³·mol⁻¹	ChemAxon
Polarizability	55.43 Å³	ChemAxon
Number of Rings	6	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

102533446

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-O-(3-O-methyl-beta-D-glucopyranosyl)-diphyllin (NP0074607)

MOL for NP0074607 (4-O-(3-O-methyl-beta-D-glucopyranosyl)-diphyllin)

3D MOL for NP0074607 (4-O-(3-O-methyl-beta-D-glucopyranosyl)-diphyllin)

3D SDF for NP0074607 (4-O-(3-O-methyl-beta-D-glucopyranosyl)-diphyllin)

3D-SDF for NP0074607 (4-O-(3-O-methyl-beta-D-glucopyranosyl)-diphyllin)

PDB for NP0074607 (4-O-(3-O-methyl-beta-D-glucopyranosyl)-diphyllin)

3D PDB for NP0074607 (4-O-(3-O-methyl-beta-D-glucopyranosyl)-diphyllin)

SMILES for NP0074607 (4-O-(3-O-methyl-beta-D-glucopyranosyl)-diphyllin)

INCHI for NP0074607 (4-O-(3-O-methyl-beta-D-glucopyranosyl)-diphyllin)

Structure for NP0074607 (4-O-(3-O-methyl-beta-D-glucopyranosyl)-diphyllin)

3D Structure for NP0074607 (4-O-(3-O-methyl-beta-D-glucopyranosyl)-diphyllin)