NP-MRD: Showing NP-Card for 16-(6-hydroxy-2h-1,3-benzodioxol-5-yl)-10-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0²,⁶.0¹¹,¹⁵]hexadeca-1,6,8,10,15-pentaen-14-one (NP0189244)

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Record Information

Version

2.0

Created at

2022-09-04 05:41:49 UTC

Updated at

2022-09-04 05:41:49 UTC

NP-MRD ID

NP0189244

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16-(6-hydroxy-2h-1,3-benzodioxol-5-yl)-10-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0²,⁶.0¹¹,¹⁵]hexadeca-1,6,8,10,15-pentaen-14-one

Description

4-(Alpha-L-Rhamnopyranosyloxy)-7,8-(methylenedioxy)-9-(6-hydroxy-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. 16-(6-hydroxy-2h-1,3-benzodioxol-5-yl)-10-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0²,⁶.0¹¹,¹⁵]hexadeca-1,6,8,10,15-pentaen-14-one is found in Acanthus mollis. Based on a literature review very few articles have been published on 4-(alpha-L-Rhamnopyranosyloxy)-7,8-(methylenedioxy)-9-(6-hydroxy-1,3-benzodioxole-5-yl)naphtho[2,3-c]furan-1(3H)-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042207412D          

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M  END

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M  END


  Mrv1652309042207412D          

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  6 25  2  0  0  0  0
 20 25  1  0  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 21 28  1  0  0  0  0
  8 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
  7 32  1  0  0  0  0
  4 33  1  0  0  0  0
 33 34  1  6  0  0  0
 33 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
  2 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0189244

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](OC2=C3C=CC4=C(OCO4)C3=C(C3=C2COC3=O)C2=CC3=C(OCO3)C=C2O)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H22O12/c1-9-20(28)21(29)22(30)26(37-9)38-23-10-2-3-14-24(36-8-33-14)18(10)17(19-12(23)6-32-25(19)31)11-4-15-16(5-13(11)27)35-7-34-15/h2-5,9,20-22,26-30H,6-8H2,1H3/t9-,20-,21+,22+,26-/m0/s1

> <INCHI_KEY>
PSTGGCDDWXYQLC-LOFOQUNOSA-N

> <FORMULA>
C26H22O12

> <MOLECULAR_WEIGHT>
526.45

> <EXACT_MASS>
526.111126148

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
50.315480686162914

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
16-(6-hydroxy-2H-1,3-benzodioxol-5-yl)-10-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0^{2,6}.0^{11,15}]hexadeca-1(16),2(6),7,9,11(15)-pentaen-14-one

> <JCHEM_LOGP>
1.582830365333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.189911047844873

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.163897854982325

> <JCHEM_PKA_STRONGEST_BASIC>
-3.61220036530493

> <JCHEM_POLAR_SURFACE_AREA>
162.6

> <JCHEM_REFRACTIVITY>
124.3206

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
16-(6-hydroxy-2H-1,3-benzodioxol-5-yl)-10-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0^{2,6}.0^{11,15}]hexadeca-1(16),2(6),7,9,11(15)-pentaen-14-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.104  -5.612   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.127  -6.762   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.636  -6.450   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.660  -7.601   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.168  -7.289   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.652  -5.827   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.628  -4.677   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.112  -3.215   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.620  -2.904   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.105  -1.442   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.081  -0.291   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.565   1.171   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.073   1.482   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.097   0.332   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.613  -1.130   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.117  -1.459   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.243   3.013   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.840   3.647   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.803   2.509   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.644  -4.054   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.152  -3.742   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.176  -4.893   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.692  -6.355   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.184  -6.666   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.160  -5.516   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.587  -4.274   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      11.435  -2.742   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.930  -2.413   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.872  -2.303   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.880  -0.763   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.621  -3.201   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.088  -4.668   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.175  -9.063   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.199 -10.213   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.667  -9.374   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.183 -10.836   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.643  -8.224   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -0.865  -8.536   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   37                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   33                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8   32                                                  
CONECT    8    7    9   29                                                  
CONECT    9    8   10   20                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15                                                            
CONECT   17   13   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   12                                                       
CONECT   20    9   21   25                                                  
CONECT   21   20   22   28                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    6   20                                                  
CONECT   26   22   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   21                                                       
CONECT   29    8   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31    7                                                       
CONECT   33    4   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35    2   38                                                  
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

View in JSmol

Synonyms

Value	Source
4-(a-L-Rhamnopyranosyloxy)-7,8-(methylenedioxy)-9-(6-hydroxy-1,3-benzodioxole-5-yl)naphtho[2,3-c]furan-1(3H)-one	Generator
4-(Α-L-rhamnopyranosyloxy)-7,8-(methylenedioxy)-9-(6-hydroxy-1,3-benzodioxole-5-yl)naphtho[2,3-c]furan-1(3H)-one	Generator

Chemical Formula

C₂₆H₂₂O₁₂

Average Mass

526.4500 Da

Monoisotopic Mass

526.11113 Da

IUPAC Name

16-(6-hydroxy-2H-1,3-benzodioxol-5-yl)-10-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0^{2,6}.0^{11,15}]hexadeca-1(16),2(6),7,9,11(15)-pentaen-14-one

Traditional Name

16-(6-hydroxy-2H-1,3-benzodioxol-5-yl)-10-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0^{2,6}.0^{11,15}]hexadeca-1(16),2(6),7,9,11(15)-pentaen-14-one

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](OC2=C3C=CC4=C(OCO4)C3=C(C3=C2COC3=O)C2=CC3=C(OCO3)C=C2O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C26H22O12/c1-9-20(28)21(29)22(30)26(37-9)38-23-10-2-3-14-24(36-8-33-14)18(10)17(19-12(23)6-32-25(19)31)11-4-15-16(5-13(11)27)35-7-34-15/h2-5,9,20-22,26-30H,6-8H2,1H3/t9-,20-,21+,22+,26-/m0/s1

InChI Key

PSTGGCDDWXYQLC-LOFOQUNOSA-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
Acanthus mollis	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
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Phenolic glycoside
Naphthofuran
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Phthalide
Isobenzofuranone
Naphthalene
Benzodioxole
Isocoumaran
1-hydroxy-2-unsubstituted benzenoid
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Lactone
Secondary alcohol
Carboxylic acid ester
Oxacycle
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Acetal
Alcohol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	1.58	ChemAxon
pKa (Strongest Acidic)	9.16	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	162.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	124.32 m³·mol⁻¹	ChemAxon
Polarizability	50.32 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	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

44205805

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 16-(6-hydroxy-2h-1,3-benzodioxol-5-yl)-10-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0²,⁶.0¹¹,¹⁵]hexadeca-1,6,8,10,15-pentaen-14-one (NP0189244)

MOL for NP0189244 (16-(6-hydroxy-2h-1,3-benzodioxol-5-yl)-10-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0²,⁶.0¹¹,¹⁵]hexadeca-1,6,8,10,15-pentaen-14-one)

3D MOL for NP0189244 (16-(6-hydroxy-2h-1,3-benzodioxol-5-yl)-10-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0²,⁶.0¹¹,¹⁵]hexadeca-1,6,8,10,15-pentaen-14-one)

3D SDF for NP0189244 (16-(6-hydroxy-2h-1,3-benzodioxol-5-yl)-10-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0²,⁶.0¹¹,¹⁵]hexadeca-1,6,8,10,15-pentaen-14-one)

3D-SDF for NP0189244 (16-(6-hydroxy-2h-1,3-benzodioxol-5-yl)-10-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0²,⁶.0¹¹,¹⁵]hexadeca-1,6,8,10,15-pentaen-14-one)

PDB for NP0189244 (16-(6-hydroxy-2h-1,3-benzodioxol-5-yl)-10-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0²,⁶.0¹¹,¹⁵]hexadeca-1,6,8,10,15-pentaen-14-one)

3D PDB for NP0189244 (16-(6-hydroxy-2h-1,3-benzodioxol-5-yl)-10-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0²,⁶.0¹¹,¹⁵]hexadeca-1,6,8,10,15-pentaen-14-one)

SMILES for NP0189244 (16-(6-hydroxy-2h-1,3-benzodioxol-5-yl)-10-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0²,⁶.0¹¹,¹⁵]hexadeca-1,6,8,10,15-pentaen-14-one)

INCHI for NP0189244 (16-(6-hydroxy-2h-1,3-benzodioxol-5-yl)-10-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0²,⁶.0¹¹,¹⁵]hexadeca-1,6,8,10,15-pentaen-14-one)

Structure for NP0189244 (16-(6-hydroxy-2h-1,3-benzodioxol-5-yl)-10-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0²,⁶.0¹¹,¹⁵]hexadeca-1,6,8,10,15-pentaen-14-one)

3D Structure for NP0189244 (16-(6-hydroxy-2h-1,3-benzodioxol-5-yl)-10-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,5,13-trioxatetracyclo[7.7.0.0²,⁶.0¹¹,¹⁵]hexadeca-1,6,8,10,15-pentaen-14-one)