NP-MRD: Showing NP-Card for 10-(2h-1,3-benzodioxol-5-yl)-16-{[(2r,3r,4r,5r)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one (NP0300956)

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Record Information

Version

2.0

Created at

2022-09-10 13:38:38 UTC

Updated at

2022-09-10 13:38:38 UTC

NP-MRD ID

NP0300956

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-(2h-1,3-benzodioxol-5-yl)-16-{[(2r,3r,4r,5r)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one

Description

10-(2H-1,3-benzodioxol-5-yl)-16-{[(2R,3R,4R,5R)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]Hexadeca-1,3(7),8,10,15-pentaen-12-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. 10-(2h-1,3-benzodioxol-5-yl)-16-{[(2r,3r,4r,5r)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one is found in Cleistanthus collinus. Based on a literature review very few articles have been published on 10-(2H-1,3-benzodioxol-5-yl)-16-{[(2R,3R,4R,5R)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]Hexadeca-1,3(7),8,10,15-pentaen-12-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102215382D          

 38 44  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309102215382D          

 38 44  0  0  1  0            999 V2000
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 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 15 20  1  0  0  0  0
 11 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
  8 26  2  0  0  0  0
 21 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 10 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
  9 33  1  0  0  0  0
  6 34  1  0  0  0  0
 34 35  1  1  0  0  0
 34 36  1  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  6  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0300956

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1CO[C@H](OC2=C3C=C4OCOC4=CC3=C(C3=C2COC3=O)C2=CC=C3OCOC3=C2)[C@H](O)[C@H]1OC

> <INCHI_IDENTIFIER>
InChI=1S/C27H24O11/c1-30-20-9-33-27(23(28)25(20)31-2)38-24-14-7-19-18(36-11-37-19)6-13(14)21(22-15(24)8-32-26(22)29)12-3-4-16-17(5-12)35-10-34-16/h3-7,20,23,25,27-28H,8-11H2,1-2H3/t20-,23-,25+,27-/m1/s1

> <INCHI_KEY>
ZXQBXVCLILMITL-KLZKGZPJSA-N

> <FORMULA>
C27H24O11

> <MOLECULAR_WEIGHT>
524.478

> <EXACT_MASS>
524.131861593

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
53.09875353741131

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-(2H-1,3-benzodioxol-5-yl)-16-{[(2R,3R,4R,5R)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(16),2,7,9,11(15)-pentaen-12-one

> <JCHEM_LOGP>
2.756073669666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.493469575372949

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.317945608032986

> <JCHEM_PKA_STRONGEST_BASIC>
-3.678801333381514

> <JCHEM_POLAR_SURFACE_AREA>
120.37000000000002

> <JCHEM_REFRACTIVITY>
127.42330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
10-(2H-1,3-benzodioxol-5-yl)-16-{[(2R,3R,4R,5R)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(16),2,7,9,11(15)-pentaen-12-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      11.592 -11.313   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.592  -9.773   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.259  -9.003   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.259  -7.463   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.925  -6.693   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.591  -7.463   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.258  -6.693   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.924   1.777   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.591   1.777   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.591   0.237   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.736   2.808   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.109   4.214   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.578   4.054   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.723  -4.859   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.628  -3.613   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.723  -2.367   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.983  -0.902   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       2.554  -3.613   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.591  -9.003   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.258  -9.773   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       8.925  -9.773   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       8.925 -11.313   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.259 -12.083   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   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   26                                                  
CONECT    9    8   10   33                                                  
CONECT   10    9   11   30                                                  
CONECT   11   10   12   21                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   11   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25    8   21                                                  
CONECT   27   24   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   23                                                       
CONECT   30   10   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32    9                                                       
CONECT   34    6   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    3   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₄O₁₁

Average Mass

524.4780 Da

Monoisotopic Mass

524.13186 Da

IUPAC Name

10-(2H-1,3-benzodioxol-5-yl)-16-{[(2R,3R,4R,5R)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(16),2,7,9,11(15)-pentaen-12-one

Traditional Name

10-(2H-1,3-benzodioxol-5-yl)-16-{[(2R,3R,4R,5R)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(16),2,7,9,11(15)-pentaen-12-one

CAS Registry Number

Not Available

SMILES

CO[C@@H]1CO[C@H](OC2=C3C=C4OCOC4=CC3=C(C3=C2COC3=O)C2=CC=C3OCOC3=C2)[C@H](O)[C@H]1OC

InChI Identifier

InChI=1S/C27H24O11/c1-30-20-9-33-27(23(28)25(20)31-2)38-24-14-7-19-18(36-11-37-19)6-13(14)21(22-15(24)8-32-26(22)29)12-3-4-16-17(5-12)35-10-34-16/h3-7,20,23,25,27-28H,8-11H2,1-2H3/t20-,23-,25+,27-/m1/s1

InChI Key

ZXQBXVCLILMITL-KLZKGZPJSA-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

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
Linear furanonaphthodioxole
Phenolic glycoside
Naphthofuran
O-glycosyl compound
Glycosyl compound
Phthalide
Isobenzofuranone
Naphthalene
Benzodioxole
Isocoumaran
Benzenoid
Oxane
Monosaccharide
Lactone
Secondary alcohol
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Alcohol
Organooxygen compound
Hydrocarbon derivative
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	2.76	ChemAxon
pKa (Strongest Acidic)	12.32	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	120.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	127.42 m³·mol⁻¹	ChemAxon
Polarizability	53.1 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

162851728

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-(2h-1,3-benzodioxol-5-yl)-16-{[(2r,3r,4r,5r)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one (NP0300956)

MOL for NP0300956 (10-(2h-1,3-benzodioxol-5-yl)-16-{[(2r,3r,4r,5r)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

3D MOL for NP0300956 (10-(2h-1,3-benzodioxol-5-yl)-16-{[(2r,3r,4r,5r)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

3D SDF for NP0300956 (10-(2h-1,3-benzodioxol-5-yl)-16-{[(2r,3r,4r,5r)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

3D-SDF for NP0300956 (10-(2h-1,3-benzodioxol-5-yl)-16-{[(2r,3r,4r,5r)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

PDB for NP0300956 (10-(2h-1,3-benzodioxol-5-yl)-16-{[(2r,3r,4r,5r)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

3D PDB for NP0300956 (10-(2h-1,3-benzodioxol-5-yl)-16-{[(2r,3r,4r,5r)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

SMILES for NP0300956 (10-(2h-1,3-benzodioxol-5-yl)-16-{[(2r,3r,4r,5r)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

INCHI for NP0300956 (10-(2h-1,3-benzodioxol-5-yl)-16-{[(2r,3r,4r,5r)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

Structure for NP0300956 (10-(2h-1,3-benzodioxol-5-yl)-16-{[(2r,3r,4r,5r)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)

3D Structure for NP0300956 (10-(2h-1,3-benzodioxol-5-yl)-16-{[(2r,3r,4r,5r)-3-hydroxy-4,5-dimethoxyoxan-2-yl]oxy}-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8,10,15-pentaen-12-one)