NP-MRD: Showing NP-Card for (3r,4e)-3-{[(2r,4ar,6r,7r,8r,8as)-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 (NP0276274)

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Record Information

Version

2.0

Created at

2022-09-09 00:18:25 UTC

Updated at

2022-09-09 00:18:25 UTC

NP-MRD ID

NP0276274

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4e)-3-{[(2r,4ar,6r,7r,8r,8as)-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

Description

(3R,4E)-3-{[(2R,4aR,6R,7R,8R,8aS)-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 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. (3r,4e)-3-{[(2r,4ar,6r,7r,8r,8as)-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 is found in Ilex pubescens. Based on a literature review very few articles have been published on (3R,4E)-3-{[(2R,4aR,6R,7R,8R,8aS)-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.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092202182D          

 33 35  0  0  1  0            999 V2000
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8592   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2881   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309092202182D          

 33 35  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0276274

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C=O)[C@H](C[C@@H]1OC[C@H]2O[C@@H](OCCC3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O1)CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O10/c1-2-14(11-24)15(9-18(26)27)10-19-31-12-17-22(33-19)20(28)21(29)23(32-17)30-8-7-13-3-5-16(25)6-4-13/h2-6,11,15,17,19-23,25,28-29H,7-10,12H2,1H3,(H,26,27)/b14-2-/t15-,17+,19+,20+,21+,22+,23+/m0/s1

> <INCHI_KEY>
NBPQOQHFVOITGU-XQZILGSASA-N

> <FORMULA>
C23H30O10

> <MOLECULAR_WEIGHT>
466.483

> <EXACT_MASS>
466.183897166

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
47.60758919665007

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4E)-3-{[(2R,4aR,6R,7R,8R,8aS)-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

> <JCHEM_LOGP>
1.170959257333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.198607282587172

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.9822264008388495

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6854030200850136

> <JCHEM_POLAR_SURFACE_AREA>
151.98000000000002

> <JCHEM_REFRACTIVITY>
114.48550000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4E)-3-{[(2R,4aR,6R,7R,8R,8aS)-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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      17.338  -2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      18.672  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      18.672  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.005  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      21.339  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.673  -5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      22.673  -6.930   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      24.006  -7.700   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      21.339  -7.700   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.005  -6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      17.338  -5.390   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      14.670  -5.390   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.670  -6.930   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12                                                       
CONECT   12   11   13   33                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   32                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   28                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   21                                                       
CONECT   28   17   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   15   33                                                  
CONECT   33   32   12                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

View in JSmol

Synonyms

Value	Source
(3R,4E)-3-{[(2R,4ar,6R,7R,8R,8as)-7,8-dihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]-hexahydro-2H-pyrano[3,2-D][1,3]dioxin-2-yl]methyl}-4-formylhex-4-enoate	Generator

Chemical Formula

C₂₃H₃₀O₁₀

Average Mass

466.4830 Da

Monoisotopic Mass

466.18390 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C(\C=O)[C@H](C[C@@H]1OC[C@H]2O[C@@H](OCCC3=CC=C(O)C=C3)[C@H](O)[C@@H](O)[C@@H]2O1)CC(O)=O

InChI Identifier

InChI=1S/C23H30O10/c1-2-14(11-24)15(9-18(26)27)10-19-31-12-17-22(33-19)20(28)21(29)23(32-17)30-8-7-13-3-5-16(25)6-4-13/h2-6,11,15,17,19-23,25,28-29H,7-10,12H2,1H3,(H,26,27)/b14-2-/t15-,17+,19+,20+,21+,22+,23+/m0/s1

InChI Key

NBPQOQHFVOITGU-XQZILGSASA-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
Medium-chain fatty acid
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Fatty acyl
Unsaturated fatty acid
Fatty acid
Benzenoid
Monocyclic benzene moiety
Meta-dioxane
Oxane
Monosaccharide
Alpha,beta-unsaturated aldehyde
Enal
1,2-diol
Secondary alcohol
Acetal
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Carbonyl group
Aldehyde
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
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

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

163189856

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,4e)-3-{[(2r,4ar,6r,7r,8r,8as)-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 (NP0276274)

MOL for NP0276274 ((3r,4e)-3-{[(2r,4ar,6r,7r,8r,8as)-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)

3D MOL for NP0276274 ((3r,4e)-3-{[(2r,4ar,6r,7r,8r,8as)-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)

3D SDF for NP0276274 ((3r,4e)-3-{[(2r,4ar,6r,7r,8r,8as)-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)

3D-SDF for NP0276274 ((3r,4e)-3-{[(2r,4ar,6r,7r,8r,8as)-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)

PDB for NP0276274 ((3r,4e)-3-{[(2r,4ar,6r,7r,8r,8as)-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)

3D PDB for NP0276274 ((3r,4e)-3-{[(2r,4ar,6r,7r,8r,8as)-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)

SMILES for NP0276274 ((3r,4e)-3-{[(2r,4ar,6r,7r,8r,8as)-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)

INCHI for NP0276274 ((3r,4e)-3-{[(2r,4ar,6r,7r,8r,8as)-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)

Structure for NP0276274 ((3r,4e)-3-{[(2r,4ar,6r,7r,8r,8as)-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)

3D Structure for NP0276274 ((3r,4e)-3-{[(2r,4ar,6r,7r,8r,8as)-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)