NP-MRD: Showing NP-Card for 9-(2h-1,3-benzodioxol-5-yl)-4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-3h-naphtho[2,3-c]furan-1-one (NP0316968)

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Record Information

Version

2.0

Created at

2022-09-11 16:31:24 UTC

Updated at

2022-09-11 16:31:24 UTC

NP-MRD ID

NP0316968

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-(2h-1,3-benzodioxol-5-yl)-4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-3h-naphtho[2,3-c]furan-1-one

Description

Diphyllin apioside 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. 9-(2h-1,3-benzodioxol-5-yl)-4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-3h-naphtho[2,3-c]furan-1-one is found in Garcinia subelliptica, Haplophyllum rosmarinifolium, Haplophyllum tuberculatum, Justicia patentiflora and Justicia procumbens. 9-(2h-1,3-benzodioxol-5-yl)-4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-3h-naphtho[2,3-c]furan-1-one was first documented in 2017 (PMID: 29221182). Based on a literature review very few articles have been published on Diphyllin apioside.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112218312D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309112218312D          

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 36 37  1  0  0  0  0
 17 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0316968

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C26H24O11/c1-31-17-6-13-14(7-18(17)32-2)22(37-25-23(28)26(30,9-27)10-34-25)15-8-33-24(29)21(15)20(13)12-3-4-16-19(5-12)36-11-35-16/h3-7,23,25,27-28,30H,8-11H2,1-2H3/t23-,25-,26+/m0/s1

> <INCHI_KEY>
XIARCTMJGANPJU-AYRHNUGRSA-N

> <FORMULA>
C26H24O11

> <MOLECULAR_WEIGHT>
512.467

> <EXACT_MASS>
512.131861593

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
50.92927375226698

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
1.3952463069999983

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.04579398333287

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.847821575164264

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1423881638379836

> <JCHEM_POLAR_SURFACE_AREA>
142.37

> <JCHEM_REFRACTIVITY>
125.29979999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-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       3.840   3.842   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.985   4.872   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  -0.770   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  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.857  -7.960   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.483  -9.367   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.015  -9.206   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.133  -2.786   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.609  -4.251   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       9.038  -1.540   0.000  0.00  0.00           O+0
HETATM   37  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   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   29                                                  
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   15                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   11    8   16                                                  
CONECT   16   15                                                            
CONECT   17    6   18   37                                                  
CONECT   18   17   19   34                                                  
CONECT   19   18   20   29                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   28                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   20                                                       
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23                                                       
CONECT   29   19    5   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30    3   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   18   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   17                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   84    0
END

View in JSmol

Synonyms

Value	Source
4-O-(beta-D-Apiofuranosyl)-6,7-dimethoxy-1-(3',4'-methylenedioxyphenyl)-3-hydroxymethylnaphthalene-2-carboxylic acid lactone	MeSH

Chemical Formula

C₂₆H₂₄O₁₁

Average Mass

512.4670 Da

Monoisotopic Mass

512.13186 Da

IUPAC Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H24O11/c1-31-17-6-13-14(7-18(17)32-2)22(37-25-23(28)26(30,9-27)10-34-25)15-8-33-24(29)21(15)20(13)12-3-4-16-19(5-12)36-11-35-16/h3-7,23,25,27-28,30H,8-11H2,1-2H3/t23-,25-,26+/m0/s1

InChI Key

XIARCTMJGANPJU-AYRHNUGRSA-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
Garcinia subelliptica	LOTUS Database	35616633
Haplophyllum rosmarinifolium	LOTUS Database	35616633
Haplophyllum tuberculatum	LOTUS Database	35616633
Justicia patentiflora	LOTUS Database	35616633
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
Lignan lactone
Arylnaphthalene lignan skeleton
Phenolic glycoside
Naphthofuran
O-glycosyl compound
Glycosyl compound
Naphthalene
Pentose monosaccharide
Phthalide
Isobenzofuranone
Isocoumaran
Benzodioxole
Anisole
Alkyl aryl ether
Monosaccharide
Benzenoid
Tertiary alcohol
Oxolane
Secondary alcohol
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Acetal
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Oxacycle
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
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	1.4	ChemAxon
pKa (Strongest Acidic)	11.85	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	142.37 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	125.3 m³·mol⁻¹	ChemAxon
Polarizability	50.93 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

8567118

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10391676

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Al-Qathama A, Gibbons S, Prieto JM: Differential modulation of Bax/Bcl-2 ratio and onset of caspase-3/7 activation induced by derivatives of Justicidin B in human melanoma cells A375. Oncotarget. 2017 Oct 6;8(56):95999-96012. doi: 10.18632/oncotarget.21625. eCollection 2017 Nov 10. [PubMed:29221182 ]
LOTUS database [Link]

Showing NP-Card for 9-(2h-1,3-benzodioxol-5-yl)-4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-3h-naphtho[2,3-c]furan-1-one (NP0316968)

MOL for NP0316968 (9-(2h-1,3-benzodioxol-5-yl)-4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-3h-naphtho[2,3-c]furan-1-one)

3D MOL for NP0316968 (9-(2h-1,3-benzodioxol-5-yl)-4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-3h-naphtho[2,3-c]furan-1-one)

3D SDF for NP0316968 (9-(2h-1,3-benzodioxol-5-yl)-4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-3h-naphtho[2,3-c]furan-1-one)

3D-SDF for NP0316968 (9-(2h-1,3-benzodioxol-5-yl)-4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-3h-naphtho[2,3-c]furan-1-one)

PDB for NP0316968 (9-(2h-1,3-benzodioxol-5-yl)-4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-3h-naphtho[2,3-c]furan-1-one)

3D PDB for NP0316968 (9-(2h-1,3-benzodioxol-5-yl)-4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-3h-naphtho[2,3-c]furan-1-one)

SMILES for NP0316968 (9-(2h-1,3-benzodioxol-5-yl)-4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-3h-naphtho[2,3-c]furan-1-one)

INCHI for NP0316968 (9-(2h-1,3-benzodioxol-5-yl)-4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-3h-naphtho[2,3-c]furan-1-one)

Structure for NP0316968 (9-(2h-1,3-benzodioxol-5-yl)-4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-3h-naphtho[2,3-c]furan-1-one)

3D Structure for NP0316968 (9-(2h-1,3-benzodioxol-5-yl)-4-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-3h-naphtho[2,3-c]furan-1-one)