NP-MRD: Showing NP-Card for 2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one (NP0272387)

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Record Information

Version

2.0

Created at

2022-09-08 18:59:24 UTC

Updated at

2022-09-08 18:59:24 UTC

NP-MRD ID

NP0272387

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one

Description

2-(4-Hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-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. 2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one is found in Daphne feddei and Daphne tangutica. Based on a literature review very few articles have been published on 2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-9-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309082220592D          

 28 31  0  0  0  0            999 V2000
    6.4895    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  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  0  0  0  0
 21 22  1  0  0  0  0
  5 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  2  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END


  Mrv1652309082220592D          

 28 31  0  0  0  0            999 V2000
    6.4895    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0770    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145    4.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    3.9849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  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  0  0  0  0
 21 22  1  0  0  0  0
  5 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 24 27  2  0  0  0  0
  3 27  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0272387

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(OC)=C1O)C1OC2=C3OC(=O)C=CC3=CC=C2OC1CO

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O8/c1-24-13-7-11(8-14(25-2)17(13)23)18-15(9-21)26-12-5-3-10-4-6-16(22)27-19(10)20(12)28-18/h3-8,15,18,21,23H,9H2,1-2H3

> <INCHI_KEY>
FCWOSPBWIBSFOO-UHFFFAOYSA-N

> <FORMULA>
C20H18O8

> <MOLECULAR_WEIGHT>
386.356

> <EXACT_MASS>
386.10016754

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
38.73765449415568

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-9-one

> <JCHEM_LOGP>
1.8314895329999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.5619200053385

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.300181637788766

> <JCHEM_PKA_STRONGEST_BASIC>
-2.99041724688408

> <JCHEM_POLAR_SURFACE_AREA>
103.68

> <JCHEM_REFRACTIVITY>
97.6586

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2H,3H-[1,4]dioxino[2,3-h]chromen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      12.114   6.105   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.344   4.771   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.804   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.034   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.494   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.184   2.104   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.206   3.437   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.724  -0.564   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.804   2.104   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.724   4.771   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.494   6.105   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.724   7.438   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.494   8.772   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.034   6.105   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.804   7.438   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   27                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
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                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23    5   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24    3   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₈O₈

Average Mass

386.3560 Da

Monoisotopic Mass

386.10017 Da

IUPAC Name

2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-9-one

Traditional Name

2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2H,3H-[1,4]dioxino[2,3-h]chromen-9-one

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(OC)=C1O)C1OC2=C3OC(=O)C=CC3=CC=C2OC1CO

InChI Identifier

InChI=1S/C20H18O8/c1-24-13-7-11(8-14(25-2)17(13)23)18-15(9-21)26-12-5-3-10-4-6-16(22)27-19(10)20(12)28-18/h3-8,15,18,21,23H,9H2,1-2H3

InChI Key

FCWOSPBWIBSFOO-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Daphne feddei	LOTUS Database	35616633
Daphne tangutica	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
M-dimethoxybenzene
Dimethoxybenzene
Benzopyran
1-benzopyran
Methoxyphenol
Anisole
Methoxybenzene
Phenoxy compound
Phenol ether
Pyranone
Phenol
Alkyl aryl ether
Para-dioxin
Pyran
Benzenoid
Monocyclic benzene moiety
Heteroaromatic compound
Lactone
Ether
Organoheterocyclic compound
Oxacycle
Primary alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Alcohol
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	1.83	ChemAxon
pKa (Strongest Acidic)	9.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	103.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.66 m³·mol⁻¹	ChemAxon
Polarizability	38.74 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

14101460

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one (NP0272387)

MOL for NP0272387 (2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

3D MOL for NP0272387 (2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

3D SDF for NP0272387 (2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

3D-SDF for NP0272387 (2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

PDB for NP0272387 (2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

3D PDB for NP0272387 (2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

SMILES for NP0272387 (2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

INCHI for NP0272387 (2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

Structure for NP0272387 (2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)

3D Structure for NP0272387 (2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-2h,3h-[1,4]dioxino[2,3-h]chromen-9-one)