NP-MRD: Showing NP-Card for ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate (NP0307355)

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Record Information

Version

2.0

Created at

2022-09-11 00:25:56 UTC

Updated at

2022-09-11 00:25:57 UTC

NP-MRD ID

NP0307355

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate

Description

Ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate belongs to the class of organic compounds known as pyranodioxins. These are polycyclic compounds containing a pyranodioxin moiety, which consists of a pyran ring fused to a dioxin ring. ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate is found in Ilex pubescens. Ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241509072D          

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M  END

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M  END


  Mrv1533004241509072D          

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 32 33  1  4  0  0  0
 31 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0307355

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)CC(CC1OCC2OC(OCCC3=CC=C(O)C=C3)C(O)C(O)C2O1)C(=CC)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O10/c1-3-16(13-26)17(11-20(28)31-4-2)12-21-33-14-19-24(35-21)22(29)23(30)25(34-19)32-10-9-15-5-7-18(27)8-6-15/h3,5-8,13,17,19,21-25,27,29-30H,4,9-12,14H2,1-2H3

> <INCHI_KEY>
AYZCBQNBHQBRIG-UHFFFAOYSA-N

> <FORMULA>
C25H34O10

> <MOLECULAR_WEIGHT>
494.537

> <EXACT_MASS>
494.215197295

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.45189009110798

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
1.6736612679999994

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.279751282978589

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.198607020887476

> <JCHEM_PKA_STRONGEST_BASIC>
-3.667510702469206

> <JCHEM_POLAR_SURFACE_AREA>
140.98000000000002

> <JCHEM_REFRACTIVITY>
124.00320000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002  -1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       9.336   0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.669   3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.003   5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.670   5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.004   6.160   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.670   3.850   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.337   3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.003  -3.850   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335 -10.780   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.002 -10.780   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.002 -12.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   31                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   30                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   29                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25   14   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   12   30                                                  
CONECT   30   29    9                                                       
CONECT   31    7   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
Ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2H-pyrano[3,2-D][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoic acid	Generator

Chemical Formula

C₂₅H₃₄O₁₀

Average Mass

494.5370 Da

Monoisotopic Mass

494.21520 Da

IUPAC Name

ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate

Traditional Name

ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate

CAS Registry Number

Not Available

SMILES

CCOC(=O)CC(CC1OCC2OC(OCCC3=CC=C(O)C=C3)C(O)C(O)C2O1)C(=CC)C=O

InChI Identifier

InChI=1S/C25H34O10/c1-3-16(13-26)17(11-20(28)31-4-2)12-21-33-14-19-24(35-21)22(29)23(30)25(34-19)32-10-9-15-5-7-18(27)8-6-15/h3,5-8,13,17,19,21-25,27,29-30H,4,9-12,14H2,1-2H3

InChI Key

AYZCBQNBHQBRIG-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

Species Name	Source	Reference
Ilex pubescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranodioxins. These are polycyclic compounds containing a pyranodioxin moiety, which consists of a pyran ring fused to a dioxin ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyranodioxins

Sub Class

Not Available

Direct Parent

Pyranodioxins

Alternative Parents

Substituents

Pyranodioxin
Tyrosol derivative
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Meta-dioxane
Monocyclic benzene moiety
Monosaccharide
Oxane
Benzenoid
Fatty acyl
Alpha,beta-unsaturated aldehyde
Enal
Secondary alcohol
Carboxylic acid ester
1,2-diol
Oxacycle
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aldehyde
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	1.93	ALOGPS
logP	1.67	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	10.2	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	140.98 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	124 m³·mol⁻¹	ChemAxon
Polarizability	51.45 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate (NP0307355)

MOL for NP0307355 (ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate)

3D MOL for NP0307355 (ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate)

3D SDF for NP0307355 (ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate)

3D-SDF for NP0307355 (ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate)

PDB for NP0307355 (ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate)

3D PDB for NP0307355 (ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate)

SMILES for NP0307355 (ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate)

INCHI for NP0307355 (ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate)

Structure for NP0307355 (ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate)

3D Structure for NP0307355 (ethyl 3-({7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2h-pyrano[3,2-d][1,3]dioxin-2-yl}methyl)-4-formylhex-4-enoate)