NP-MRD: Showing NP-Card for [(3s,4r,5s)-5-{[9-(2h-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-3h-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate (NP0293426)

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Record Information

Version

2.0

Created at

2022-09-10 01:25:27 UTC

Updated at

2022-09-10 01:25:27 UTC

NP-MRD ID

NP0293426

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(3s,4r,5s)-5-{[9-(2h-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-3h-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate

Description

Diphyllin apioside 5''-acetate 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. [(3s,4r,5s)-5-{[9-(2h-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-3h-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate is found in Justicia procumbens. Based on a literature review very few articles have been published on Diphyllin apioside 5''-acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102203252D          

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M  END

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M  END


  Mrv1652309102203252D          

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 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 11 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  1  0  0  0
  6 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 26 31  1  0  0  0  0
 22 32  1  0  0  0  0
  5 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
  3 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 21 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
 20 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0293426

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C2C(=C1)C(O[C@@H]1OC[C@](O)(COC(C)=O)[C@H]1O)=C1COC(=O)C1=C2C1=CC=C2OCOC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H26O12/c1-13(29)36-10-28(32)11-37-27(25(28)30)40-24-16-8-20(34-3)19(33-2)7-15(16)22(23-17(24)9-35-26(23)31)14-4-5-18-21(6-14)39-12-38-18/h4-8,25,27,30,32H,9-12H2,1-3H3/t25-,27-,28+/m0/s1

> <INCHI_KEY>
UOOSHUGMIURKRC-RZDMPUFOSA-N

> <FORMULA>
C28H26O12

> <MOLECULAR_WEIGHT>
554.504

> <EXACT_MASS>
554.142426277

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
55.22482587097761

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(3S,4R,5S)-5-{[9-(2H-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-1H,3H-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate

> <JCHEM_LOGP>
1.8363717173333312

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.0321914905943

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.832175118549804

> <JCHEM_PKA_STRONGEST_BASIC>
-4.046211255069598

> <JCHEM_POLAR_SURFACE_AREA>
148.44

> <JCHEM_REFRACTIVITY>
134.45129999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(3S,4R,5S)-5-{[9-(2H-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-3H-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate

> <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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.594   1.684   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.564   2.828   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.334   4.162   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.927   4.788   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.810   5.626   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.316   5.947   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.792   7.411   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.298   7.731   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.761   8.556   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.840   3.842   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.985   4.872   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.857  -7.960   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.483  -9.367   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.015  -9.206   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       8.609  -4.251   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       9.038  -1.540   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       8.133  -0.294   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   32                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   18                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   11    8   19                                                  
CONECT   19   18                                                            
CONECT   20    6   21   40                                                  
CONECT   21   20   22   37                                                  
CONECT   22   21   23   32                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   23                                                       
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32   22    5   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33    3   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   21   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   20                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
Diphyllin apioside 5''-acetic acid	Generator

Chemical Formula

C₂₈H₂₆O₁₂

Average Mass

554.5040 Da

Monoisotopic Mass

554.14243 Da

IUPAC Name

[(3S,4R,5S)-5-{[9-(2H-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-1H,3H-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate

Traditional Name

[(3S,4R,5S)-5-{[9-(2H-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-3H-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C2C(=C1)C(O[C@@H]1OC[C@](O)(COC(C)=O)[C@H]1O)=C1COC(=O)C1=C2C1=CC=C2OCOC2=C1

InChI Identifier

InChI=1S/C28H26O12/c1-13(29)36-10-28(32)11-37-27(25(28)30)40-24-16-8-20(34-3)19(33-2)7-15(16)22(23-17(24)9-35-26(23)31)14-4-5-18-21(6-14)39-12-38-18/h4-8,25,27,30,32H,9-12H2,1-3H3/t25-,27-,28+/m0/s1

InChI Key

UOOSHUGMIURKRC-RZDMPUFOSA-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
Justicia procumbens	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
Glycosyl compound
O-glycosyl compound
Isobenzofuranone
Naphthalene
Phthalide
Pentose monosaccharide
Isocoumaran
Benzodioxole
Anisole
Alkyl aryl ether
Dicarboxylic acid or derivatives
Benzenoid
Monosaccharide
Tetrahydrofuran
Tertiary alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
1,2-diol
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Alcohol
Carbonyl group
Organooxygen compound
Organic oxygen compound
Organic oxide
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	1.84	ChemAxon
pKa (Strongest Acidic)	11.83	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	148.44 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	134.45 m³·mol⁻¹	ChemAxon
Polarizability	55.22 Å³	ChemAxon
Number of Rings	6	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

8523080

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10347622

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(3s,4r,5s)-5-{[9-(2h-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-3h-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate (NP0293426)

MOL for NP0293426 ([(3s,4r,5s)-5-{[9-(2h-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-3h-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate)

3D MOL for NP0293426 ([(3s,4r,5s)-5-{[9-(2h-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-3h-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate)

3D SDF for NP0293426 ([(3s,4r,5s)-5-{[9-(2h-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-3h-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate)

3D-SDF for NP0293426 ([(3s,4r,5s)-5-{[9-(2h-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-3h-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate)

PDB for NP0293426 ([(3s,4r,5s)-5-{[9-(2h-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-3h-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate)

3D PDB for NP0293426 ([(3s,4r,5s)-5-{[9-(2h-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-3h-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate)

SMILES for NP0293426 ([(3s,4r,5s)-5-{[9-(2h-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-3h-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate)

INCHI for NP0293426 ([(3s,4r,5s)-5-{[9-(2h-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-3h-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate)

Structure for NP0293426 ([(3s,4r,5s)-5-{[9-(2h-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-3h-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate)

3D Structure for NP0293426 ([(3s,4r,5s)-5-{[9-(2h-1,3-benzodioxol-5-yl)-6,7-dimethoxy-1-oxo-3h-naphtho[2,3-c]furan-4-yl]oxy}-3,4-dihydroxyoxolan-3-yl]methyl acetate)