NP-MRD: Showing NP-Card for (2s,3s)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2r)-8-oxo-2h-[1,3]dioxolo[4,5-h]chromen-2-yl]-2h-[1,4]dioxino[2,3-h]chromen-9-one (NP0157144)

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Record Information

Version

2.0

Created at

2022-09-02 14:27:59 UTC

Updated at

2022-09-02 14:27:59 UTC

NP-MRD ID

NP0157144

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3s)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2r)-8-oxo-2h-[1,3]dioxolo[4,5-h]chromen-2-yl]-2h-[1,4]dioxino[2,3-h]chromen-9-one

Description

(2S,3S)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2R)-8-oxo-2H,8H-[1,3]dioxolo[4,5-h]chromen-2-yl]-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-9-one belongs to the class of organic compounds known as coumarinolignans. These are lignans with a structure characterized by the presence of a 1,4-dioxane bridge substituted by a phenyl group, and fused to a coumarin. (2s,3s)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2r)-8-oxo-2h-[1,3]dioxolo[4,5-h]chromen-2-yl]-2h-[1,4]dioxino[2,3-h]chromen-9-one is found in Daphne feddei. Based on a literature review very few articles have been published on (2S,3S)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2R)-8-oxo-2H,8H-[1,3]dioxolo[4,5-h]chromen-2-yl]-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-9-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022216282D          

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M  END

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  Mrv1652309022216282D          

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  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  2  0  0  0  0
 12 18  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  0  0  0  0
  6 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  1  0  0  0
 22 23  1  1  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 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
 27 33  1  0  0  0  0
 33 34  2  0  0  0  0
 24 34  1  0  0  0  0
 34 35  1  0  0  0  0
 22 35  1  0  0  0  0
  5 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 37 40  2  0  0  0  0
  3 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0157144

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1O)[C@@H]1OC2=C3OC(=O)C=CC3=CC=C2O[C@]1(O)[C@@H]1OC2=CC=C3C=CC(=O)OC3=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C29H20O12/c1-34-18-11-15(12-19(35-2)22(18)32)27-29(33,41-17-8-4-14-6-10-21(31)38-24(14)26(17)39-27)28-36-16-7-3-13-5-9-20(30)37-23(13)25(16)40-28/h3-12,27-28,32-33H,1-2H3/t27-,28+,29-/m0/s1

> <INCHI_KEY>
YDQKXWUGHNARIP-NHKHRBQYSA-N

> <FORMULA>
C29H20O12

> <MOLECULAR_WEIGHT>
560.467

> <EXACT_MASS>
560.095476084

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
53.79817811764225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2R)-8-oxo-2H,8H-[1,3]dioxolo[4,5-h]chromen-2-yl]-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-9-one

> <ALOGPS_LOGP>
3.52

> <JCHEM_LOGP>
3.7827527709999997

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.546093791716306

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.894892249472969

> <JCHEM_PKA_STRONGEST_BASIC>
-4.249552230837692

> <JCHEM_POLAR_SURFACE_AREA>
148.44

> <JCHEM_REFRACTIVITY>
138.1082

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.43e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2R)-8-oxo-2H-[1,3]dioxolo[4,5-h]chromen-2-yl]-2H-[1,4]dioxino[2,3-h]chromen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      10.719   1.792   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.862   0.512   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.326   0.614   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.469  -0.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.932  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.076  -1.844   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.539  -1.742   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.683  -3.022   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.363  -4.404   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.507  -5.684   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.970  -5.582   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.290  -4.200   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.247  -4.098   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.927  -2.717   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.071  -1.437   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.751  -0.055   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.466  -1.539   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.146  -2.920   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.900  -4.505   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.756  -3.226   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.161  -2.594   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.065  -4.037   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.178  -5.573   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.674  -5.940   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.402  -7.297   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.941  -7.345   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.752  -6.036   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.292  -6.084   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.103  -4.775   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.375  -3.418   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.186  -2.109   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      11.836  -3.370   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      11.024  -4.679   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.485  -4.631   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.491  -3.455   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.252   0.818   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.109   2.097   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.429   3.479   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       6.285   4.759   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.645   1.996   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       8.502   3.276   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   40                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   36                                                  
CONECT    6    5    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17    8   12                                                  
CONECT   19    9   20                                                       
CONECT   20   19    6   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23   35                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   34                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   33                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   27   34                                                  
CONECT   34   33   24   35                                                  
CONECT   35   34   22                                                       
CONECT   36    5   37                                                       
CONECT   37   36   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
CONECT   40   37    3   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₂₀O₁₂

Average Mass

560.4670 Da

Monoisotopic Mass

560.09548 Da

IUPAC Name

(2S,3S)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2R)-8-oxo-2H,8H-[1,3]dioxolo[4,5-h]chromen-2-yl]-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-9-one

Traditional Name

(2S,3S)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2R)-8-oxo-2H-[1,3]dioxolo[4,5-h]chromen-2-yl]-2H-[1,4]dioxino[2,3-h]chromen-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1O)[C@@H]1OC2=C3OC(=O)C=CC3=CC=C2O[C@]1(O)[C@@H]1OC2=CC=C3C=CC(=O)OC3=C2O1

InChI Identifier

InChI=1S/C29H20O12/c1-34-18-11-15(12-19(35-2)22(18)32)27-29(33,41-17-8-4-14-6-10-21(31)38-24(14)26(17)39-27)28-36-16-7-3-13-5-9-20(30)37-23(13)25(16)40-28/h3-12,27-28,32-33H,1-2H3/t27-,28+,29-/m0/s1

InChI Key

YDQKXWUGHNARIP-NHKHRBQYSA-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
Daphne feddei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarinolignans. These are lignans with a structure characterized by the presence of a 1,4-dioxane bridge substituted by a phenyl group, and fused to a coumarin.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Coumarinolignans

Sub Class

Not Available

Direct Parent

Coumarinolignans

Alternative Parents

Substituents

Angular-fused coumarolignan skeleton
2-phenylbenzo-1,4-dioxane
Phenylbenzodioxane
P-dioxolo[2,3-h]coumarin
Coumarin
Benzo-1,4-dioxane
Benzodioxane
Benzopyran
Methoxyphenol
1-benzopyran
Dimethoxybenzene
M-dimethoxybenzene
Benzodioxole
Methoxybenzene
Phenol ether
Anisole
Phenoxy compound
Pyranone
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Pyran
Para-dioxin
Benzenoid
Heteroaromatic compound
Hemiacetal
Lactone
Oxacycle
Organoheterocyclic compound
Acetal
Ether
Organic oxygen compound
Organooxygen compound
Organic oxide
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	3.52	ALOGPS
logP	3.78	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	8.89	ChemAxon
pKa (Strongest Basic)	-4.2	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	4	ChemAxon
Refractivity	138.11 m³·mol⁻¹	ChemAxon
Polarizability	53.8 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

162917604

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3s)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2r)-8-oxo-2h-[1,3]dioxolo[4,5-h]chromen-2-yl]-2h-[1,4]dioxino[2,3-h]chromen-9-one (NP0157144)

MOL for NP0157144 ((2s,3s)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2r)-8-oxo-2h-[1,3]dioxolo[4,5-h]chromen-2-yl]-2h-[1,4]dioxino[2,3-h]chromen-9-one)

3D MOL for NP0157144 ((2s,3s)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2r)-8-oxo-2h-[1,3]dioxolo[4,5-h]chromen-2-yl]-2h-[1,4]dioxino[2,3-h]chromen-9-one)

3D SDF for NP0157144 ((2s,3s)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2r)-8-oxo-2h-[1,3]dioxolo[4,5-h]chromen-2-yl]-2h-[1,4]dioxino[2,3-h]chromen-9-one)

3D-SDF for NP0157144 ((2s,3s)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2r)-8-oxo-2h-[1,3]dioxolo[4,5-h]chromen-2-yl]-2h-[1,4]dioxino[2,3-h]chromen-9-one)

PDB for NP0157144 ((2s,3s)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2r)-8-oxo-2h-[1,3]dioxolo[4,5-h]chromen-2-yl]-2h-[1,4]dioxino[2,3-h]chromen-9-one)

3D PDB for NP0157144 ((2s,3s)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2r)-8-oxo-2h-[1,3]dioxolo[4,5-h]chromen-2-yl]-2h-[1,4]dioxino[2,3-h]chromen-9-one)

SMILES for NP0157144 ((2s,3s)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2r)-8-oxo-2h-[1,3]dioxolo[4,5-h]chromen-2-yl]-2h-[1,4]dioxino[2,3-h]chromen-9-one)

INCHI for NP0157144 ((2s,3s)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2r)-8-oxo-2h-[1,3]dioxolo[4,5-h]chromen-2-yl]-2h-[1,4]dioxino[2,3-h]chromen-9-one)

Structure for NP0157144 ((2s,3s)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2r)-8-oxo-2h-[1,3]dioxolo[4,5-h]chromen-2-yl]-2h-[1,4]dioxino[2,3-h]chromen-9-one)

3D Structure for NP0157144 ((2s,3s)-3-hydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-[(2r)-8-oxo-2h-[1,3]dioxolo[4,5-h]chromen-2-yl]-2h-[1,4]dioxino[2,3-h]chromen-9-one)