NP-MRD: Showing NP-Card for 4-[2-(hydroxymethyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate (NP0221224)

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Record Information

Version

2.0

Created at

2022-09-05 22:44:27 UTC

Updated at

2022-09-05 22:44:27 UTC

NP-MRD ID

NP0221224

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[2-(hydroxymethyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate

Description

4-[2-(Hydroxymethyl)-5-methoxy-9-oxo-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate 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. 4-[2-(Hydroxymethyl)-5-methoxy-9-oxo-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191518032D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004191518032D          

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 22 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 20 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0221224

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1OC(=O)C=CC1=CC=CC=C1)C1OC2=C(OC)C=C3C=CC(=O)OC3=C2OC1CO

> <INCHI_IDENTIFIER>
InChI=1S/C29H24O9/c1-33-21-14-18(9-11-20(21)35-24(31)12-8-17-6-4-3-5-7-17)26-23(16-30)36-29-27-19(10-13-25(32)37-27)15-22(34-2)28(29)38-26/h3-15,23,26,30H,16H2,1-2H3

> <INCHI_KEY>
ZALKVTNQFICYGP-UHFFFAOYSA-N

> <FORMULA>
C29H24O9

> <MOLECULAR_WEIGHT>
516.502

> <EXACT_MASS>
516.142032353

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
52.84682565649224

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[2-(hydroxymethyl)-5-methoxy-9-oxo-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate

> <ALOGPS_LOGP>
3.98

> <JCHEM_LOGP>
4.335081136666667

> <ALOGPS_LOGS>
-5.21

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.561738254035301

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9904956876849598

> <JCHEM_POLAR_SURFACE_AREA>
109.75000000000001

> <JCHEM_REFRACTIVITY>
137.2263

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[2-(hydroxymethyl)-5-methoxy-9-oxo-2H,3H-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -2.365   1.127   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.825   1.127   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.055  -0.206   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.485  -0.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.255  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.485  -2.874   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.055  -2.874   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.825  -1.540   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.365  -1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.135  -2.874   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.365  -4.207   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.675  -2.874   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.445  -4.207   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.985  -4.207   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.755  -5.541   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -9.295  -5.541   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -10.065  -4.207   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.295  -2.874   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -7.755  -2.874   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.565  -0.206   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.105   2.461   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.875   3.795   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.495  -4.207   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       9.185  -2.874   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.105  -2.874   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.795  -4.207   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       2.255  -4.207   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    5   21   36                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   34                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   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   22   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   20   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
4-[2-(Hydroxymethyl)-5-methoxy-9-oxo-2H,3H,9H-[1,4]dioxino[2,3-H]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₂₉H₂₄O₉

Average Mass

516.5020 Da

Monoisotopic Mass

516.14203 Da

IUPAC Name

4-[2-(hydroxymethyl)-5-methoxy-9-oxo-2H,3H,9H-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate

Traditional Name

4-[2-(hydroxymethyl)-5-methoxy-9-oxo-2H,3H-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1OC(=O)C=CC1=CC=CC=C1)C1OC2=C(OC)C=C3C=CC(=O)OC3=C2OC1CO

InChI Identifier

InChI=1S/C29H24O9/c1-33-21-14-18(9-11-20(21)35-24(31)12-8-17-6-4-3-5-7-17)26-23(16-30)36-29-27-19(10-13-25(32)37-27)15-22(34-2)28(29)38-26/h3-15,23,26,30H,16H2,1-2H3

InChI Key

ZALKVTNQFICYGP-UHFFFAOYSA-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

Not Available

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
Cinnamic acid ester
Cinnamic acid or derivatives
Coumarin
Phenol ester
Benzopyran
1-benzopyran
Benzodioxane
Benzo-1,4-dioxane
Methoxybenzene
Phenol ether
Phenoxy compound
Styrene
Anisole
Pyranone
Fatty acid ester
Alkyl aryl ether
Pyran
Para-dioxin
Benzenoid
Fatty acyl
Monocyclic benzene moiety
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Primary alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
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	3.98	ALOGPS
logP	4.34	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	14.56	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	109.75 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	137.23 m³·mol⁻¹	ChemAxon
Polarizability	52.85 Å³	ChemAxon
Number of Rings	5	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

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

75163293

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[2-(hydroxymethyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate (NP0221224)

MOL for NP0221224 (4-[2-(hydroxymethyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate)

3D MOL for NP0221224 (4-[2-(hydroxymethyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate)

3D SDF for NP0221224 (4-[2-(hydroxymethyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate)

3D-SDF for NP0221224 (4-[2-(hydroxymethyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate)

PDB for NP0221224 (4-[2-(hydroxymethyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate)

3D PDB for NP0221224 (4-[2-(hydroxymethyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate)

SMILES for NP0221224 (4-[2-(hydroxymethyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate)

INCHI for NP0221224 (4-[2-(hydroxymethyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate)

Structure for NP0221224 (4-[2-(hydroxymethyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate)

3D Structure for NP0221224 (4-[2-(hydroxymethyl)-5-methoxy-9-oxo-2h,3h-[1,4]dioxino[2,3-h]chromen-3-yl]-2-methoxyphenyl 3-phenylprop-2-enoate)