NP-MRD: Showing NP-Card for Diphyllin O-glucoside (NP0138699)

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Record Information

Version

2.0

Created at

2022-06-29 17:41:30 UTC

Updated at

2022-06-29 17:41:30 UTC

NP-MRD ID

NP0138699

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Diphyllin O-glucoside

Description

Cleistanthin B, also known as clei b, 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. Diphyllin O-glucoside is found in Cleistanthus collinus, Diphylleia cymosa, Haplophyllum buxbaumii and Haplophyllum cappadocicum. Diphyllin O-glucoside was first documented in 2014 (PMID: 25316991). Based on a literature review a small amount of articles have been published on cleistanthin B (PMID: 33668694) (PMID: 27774423) (PMID: 27767340).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652306292219412D          

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 10 27  1  0  0  0  0
 27 28  2  0  0  0  0
  9 29  1  0  0  0  0
 29 30  2  0  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
 29 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 31 37  1  0  0  0  0
  4 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0138699

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C2C(=C1)C(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=C1COC(=O)C1=C2C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H26O12/c1-33-16-6-12-13(7-17(16)34-2)25(39-27-24(31)23(30)22(29)19(8-28)38-27)14-9-35-26(32)21(14)20(12)11-3-4-15-18(5-11)37-10-36-15/h3-7,19,22-24,27-31H,8-10H2,1-2H3/t19-,22-,23+,24-,27+/m1/s1

> <INCHI_KEY>
BJGIWVGXMRUMNA-WBYCZGBQSA-N

> <FORMULA>
C27H26O12

> <MOLECULAR_WEIGHT>
542.493

> <EXACT_MASS>
542.142426277

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
53.6949149253125

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.19

> <JCHEM_LOGP>
0.900909721333333

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.031414194687656

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.176803425409066

> <JCHEM_PKA_STRONGEST_BASIC>
-2.98109234741293

> <JCHEM_POLAR_SURFACE_AREA>
162.6

> <JCHEM_REFRACTIVITY>
131.0429

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.10e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.812   2.570   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.185   3.977   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.654   3.816   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.623   4.961   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -5.466   4.326   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -6.371   3.080   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -5.466   1.834   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   38                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    3                                                       
CONECT    9    7   10   29                                                  
CONECT   10    9   11   27                                                  
CONECT   11   10   12   25                                                  
CONECT   12   11    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   17                                                            
CONECT   23   16                                                            
CONECT   24   15                                                            
CONECT   25   11   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   10   28                                                  
CONECT   28   27                                                            
CONECT   29    9   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   32   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   31                                                       
CONECT   38    4   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Value	Source
4-O-(beta-D-Glucopyranosyl)diphyllin	ChEBI
9-(1,3-Benzodioxol-5-yl)-4-(beta-D-glucopyranosyloxy)-6,7-dimethoxynaphtho[2,3-c]furan-1(3H)-one	ChEBI
Clei b	ChEBI
Diphyllin beta-D-glucoside	ChEBI
4-O-(b-D-Glucopyranosyl)diphyllin	Generator
4-O-(Β-D-glucopyranosyl)diphyllin	Generator
9-(1,3-Benzodioxol-5-yl)-4-(b-D-glucopyranosyloxy)-6,7-dimethoxynaphtho[2,3-c]furan-1(3H)-one	Generator
9-(1,3-Benzodioxol-5-yl)-4-(β-D-glucopyranosyloxy)-6,7-dimethoxynaphtho[2,3-c]furan-1(3H)-one	Generator
Diphyllin b-D-glucoside	Generator
Diphyllin β-D-glucoside	Generator
9-(1,3-Benzodioxol-5-yl)-4-(beta-D-glucopyranosyloxy)-6,7-dimethoxynaphtho(2,3-c)furan-1(3H)-one	MeSH

Chemical Formula

C₂₇H₂₆O₁₂

Average Mass

542.4930 Da

Monoisotopic Mass

542.14243 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

30021-77-3

SMILES

COC1=C(OC)C=C2C(=C1)C(O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)=C1COC(=O)C1=C2C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C27H26O12/c1-33-16-6-12-13(7-17(16)34-2)25(39-27-24(31)23(30)22(29)19(8-28)38-27)14-9-35-26(32)21(14)20(12)11-3-4-15-18(5-11)37-10-36-15/h3-7,19,22-24,27-31H,8-10H2,1-2H3/t19-,22-,23+,24-,27+/m1/s1

InChI Key

BJGIWVGXMRUMNA-WBYCZGBQSA-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
Cleistanthus collinus	LOTUS Database	35616633
Diphylleia cymosa	LOTUS Database	35616633
Haplophyllum buxbaumii	LOTUS Database	35616633
Haplophyllum cappadocicum	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
Arylnaphthalene lignan skeleton
Lignan lactone
Phenolic glycoside
Naphthofuran
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Isobenzofuranone
Naphthalene
Phthalide
Isocoumaran
Benzodioxole
Anisole
Alkyl aryl ether
Monosaccharide
Oxane
Benzenoid
Carboxylic acid ester
Secondary alcohol
Lactone
Organoheterocyclic compound
Ether
Acetal
Carboxylic acid derivative
Oxacycle
Polyol
Monocarboxylic acid or derivatives
Primary alcohol
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

beta-D-glucoside (CHEBI:84407 )
monosaccharide derivative (CHEBI:84407 )
cleistanthins (CHEBI:84407 )

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

106688

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119458

PDB ID

Not Available

ChEBI ID

84407

Good Scents ID

Not Available

References

General References

Stefanik M, Strakova P, Haviernik J, Miller AD, Ruzek D, Eyer L: Antiviral Activity of Vacuolar ATPase Blocker Diphyllin against SARS-CoV-2. Microorganisms. 2021 Feb 25;9(3). pii: microorganisms9030471. doi: 10.3390/microorganisms9030471. [PubMed:33668694 ]
Thummar VR, Parasuraman S, Basu D, Raveendran R: Evaluation of in vivo antitumor activity of cleistanthin B in Swiss albino mice. J Tradit Complement Med. 2015 Sep 3;6(4):383-388. doi: 10.1016/j.jtcme.2015.08.004. eCollection 2016 Oct. [PubMed:27774423 ]
Priyadharsini RP, Parasuraman S, Raveendran R: Evaluation of the antihypertensive activity and alpha adrenergic receptor interaction of cleistanthins A and B. J Basic Clin Pharm. 2014 Sep;5(4):109-14. doi: 10.4103/0976-0105.141950. [PubMed:25316991 ]
Jin H, Yang S, Dong JX: New lignan glycosides from Justicia procumbens. J Asian Nat Prod Res. 2017 Jan;19(1):1-8. doi: 10.1080/10286020.2016.1241771. Epub 2016 Oct 21. [PubMed:27767340 ]

Showing NP-Card for Diphyllin O-glucoside (NP0138699)

MOL for NP0138699 (Diphyllin O-glucoside)

3D MOL for NP0138699 (Diphyllin O-glucoside)

3D SDF for NP0138699 (Diphyllin O-glucoside)

3D-SDF for NP0138699 (Diphyllin O-glucoside)

PDB for NP0138699 (Diphyllin O-glucoside)

3D PDB for NP0138699 (Diphyllin O-glucoside)

SMILES for NP0138699 (Diphyllin O-glucoside)

INCHI for NP0138699 (Diphyllin O-glucoside)

Structure for NP0138699 (Diphyllin O-glucoside)

3D Structure for NP0138699 (Diphyllin O-glucoside)