NP-MRD: Showing NP-Card for (2E,6R)-2,6-Dimethyl-8-hydroxy-2-octenoic acid 8-O-[6'-O-(E)-p-coumaroyl]-beta-D-glucopyranoside (NP0072019)

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Record Information

Version

2.0

Created at

2022-04-28 17:24:10 UTC

Updated at

2022-04-28 17:24:11 UTC

NP-MRD ID

NP0072019

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2E,6R)-2,6-Dimethyl-8-hydroxy-2-octenoic acid 8-O-[6'-O-(E)-p-coumaroyl]-beta-D-glucopyranoside

Description

9-(2H-1,3-benzodioxol-5-yl)-4-{[(2R,3S,4S,5S)-3,4-dimethoxy-5-(methoxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-1H,3H-naphtho[2,3-c]furan-1-one belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones. (2E,6R)-2,6-Dimethyl-8-hydroxy-2-octenoic acid 8-O-[6'-O-(E)-p-coumaroyl]-beta-D-glucopyranoside is found in Catalpa ovata G.DON. . Based on a literature review very few articles have been published on 9-(2H-1,3-benzodioxol-5-yl)-4-{[(2R,3S,4S,5S)-3,4-dimethoxy-5-(methoxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-1H,3H-naphtho[2,3-c]furan-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282219242D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282219242D          

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    0.8671   -5.1657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3822   -5.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1715   -2.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9920   -2.5432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3276   -1.7895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1345   -1.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  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
  7 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  4 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 24  1  0  0  0  0
 25 24  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 28 32  1  1  0  0  0
 32 33  1  0  0  0  0
 27 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
  2 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
  1 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0072019

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC[C@@H]1O[C@H](OC2=C3C=C(OC)C(OC)=CC3=C(C3=C2COC3=O)C2=CC3=C(OCO3)C=C2)[C@@H](OC)[C@H]1OC

> <INCHI_IDENTIFIER>
InChI=1S/C29H30O11/c1-31-12-22-26(34-4)27(35-5)29(39-22)40-25-16-10-20(33-3)19(32-2)9-15(16)23(24-17(25)11-36-28(24)30)14-6-7-18-21(8-14)38-13-37-18/h6-10,22,26-27,29H,11-13H2,1-5H3/t22-,26-,27-,29+/m0/s1

> <INCHI_KEY>
XKNYFHSUBJVWQX-WDDJKNHOSA-N

> <FORMULA>
C29H30O11

> <MOLECULAR_WEIGHT>
554.548

> <EXACT_MASS>
554.178811786

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
57.577657012170995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-(2H-1,3-benzodioxol-5-yl)-4-{[(2R,3S,4S,5S)-3,4-dimethoxy-5-(methoxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-1H,3H-naphtho[2,3-c]furan-1-one

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
3.460624174333333

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.458924889848667

> <JCHEM_PKA_STRONGEST_BASIC>
-3.543789983956881

> <JCHEM_POLAR_SURFACE_AREA>
109.37000000000003

> <JCHEM_REFRACTIVITY>
139.33399999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.51e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(2H-1,3-benzodioxol-5-yl)-4-{[(2R,3S,4S,5S)-3,4-dimethoxy-5-(methoxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-3H-naphtho[2,3-c]furan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.799   2.016   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -7.705   0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.799  -0.476   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.421  -5.525   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.897  -6.990   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.437  -6.990   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.913  -5.525   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.378  -5.049   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       5.698  -3.543   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.343  -8.236   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.874  -8.075   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.992  -8.236   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.619  -9.643   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       0.713 -10.888   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.320  -4.586   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.852  -4.747   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -2.478  -3.340   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -3.984  -3.020   0.000  0.00  0.00           O+0
CONECT    1    2    6   39                                                  
CONECT    2    1    3   37                                                  
CONECT    3    2    4   24                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    9                                                       
CONECT   16    5   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18    4                                                       
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   17   23                                                       
CONECT   23   22                                                            
CONECT   24    3   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29   32                                                  
CONECT   29   28   25   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   28   33                                                       
CONECT   33   32                                                            
CONECT   34   27   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37    2   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38    1   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₀O₁₁

Average Mass

554.5480 Da

Monoisotopic Mass

554.17881 Da

IUPAC Name

9-(2H-1,3-benzodioxol-5-yl)-4-{[(2R,3S,4S,5S)-3,4-dimethoxy-5-(methoxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-1H,3H-naphtho[2,3-c]furan-1-one

Traditional Name

9-(2H-1,3-benzodioxol-5-yl)-4-{[(2R,3S,4S,5S)-3,4-dimethoxy-5-(methoxymethyl)oxolan-2-yl]oxy}-6,7-dimethoxy-3H-naphtho[2,3-c]furan-1-one

CAS Registry Number

Not Available

SMILES

COC[C@@H]1O[C@H](OC2=C3C=C(OC)C(OC)=CC3=C(C3=C2COC3=O)C2=CC3=C(OCO3)C=C2)[C@@H](OC)[C@H]1OC

InChI Identifier

InChI=1S/C29H30O11/c1-31-12-22-26(34-4)27(35-5)29(39-22)40-25-16-10-20(33-3)19(32-2)9-15(16)23(24-17(25)11-36-28(24)30)14-6-7-18-21(8-14)38-13-37-18/h6-10,22,26-27,29H,11-13H2,1-5H3/t22-,26-,27-,29+/m0/s1

InChI Key

XKNYFHSUBJVWQX-WDDJKNHOSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Catalpa ovata G.DON.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
Lignan lactone
Arylnaphthalene lignan skeleton
Phenolic glycoside
Naphthofuran
O-glycosyl compound
Glycosyl compound
Isobenzofuranone
Phthalide
Pentose monosaccharide
Naphthalene
Isocoumaran
Benzodioxole
Anisole
Alkyl aryl ether
Benzenoid
Monosaccharide
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
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	3.07	ALOGPS
logP	3.46	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	13.46	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	109.37 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	139.33 m³·mol⁻¹	ChemAxon
Polarizability	57.58 Å³	ChemAxon
Number of Rings	6	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

163086022

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (2E,6R)-2,6-Dimethyl-8-hydroxy-2-octenoic acid 8-O-[6'-O-(E)-p-coumaroyl]-beta-D-glucopyranoside (NP0072019)

MOL for NP0072019 ((2E,6R)-2,6-Dimethyl-8-hydroxy-2-octenoic acid 8-O-[6'-O-(E)-p-coumaroyl]-beta-D-glucopyranoside)

3D MOL for NP0072019 ((2E,6R)-2,6-Dimethyl-8-hydroxy-2-octenoic acid 8-O-[6'-O-(E)-p-coumaroyl]-beta-D-glucopyranoside)

3D SDF for NP0072019 ((2E,6R)-2,6-Dimethyl-8-hydroxy-2-octenoic acid 8-O-[6'-O-(E)-p-coumaroyl]-beta-D-glucopyranoside)

3D-SDF for NP0072019 ((2E,6R)-2,6-Dimethyl-8-hydroxy-2-octenoic acid 8-O-[6'-O-(E)-p-coumaroyl]-beta-D-glucopyranoside)

PDB for NP0072019 ((2E,6R)-2,6-Dimethyl-8-hydroxy-2-octenoic acid 8-O-[6'-O-(E)-p-coumaroyl]-beta-D-glucopyranoside)

3D PDB for NP0072019 ((2E,6R)-2,6-Dimethyl-8-hydroxy-2-octenoic acid 8-O-[6'-O-(E)-p-coumaroyl]-beta-D-glucopyranoside)

SMILES for NP0072019 ((2E,6R)-2,6-Dimethyl-8-hydroxy-2-octenoic acid 8-O-[6'-O-(E)-p-coumaroyl]-beta-D-glucopyranoside)

INCHI for NP0072019 ((2E,6R)-2,6-Dimethyl-8-hydroxy-2-octenoic acid 8-O-[6'-O-(E)-p-coumaroyl]-beta-D-glucopyranoside)

Structure for NP0072019 ((2E,6R)-2,6-Dimethyl-8-hydroxy-2-octenoic acid 8-O-[6'-O-(E)-p-coumaroyl]-beta-D-glucopyranoside)

3D Structure for NP0072019 ((2E,6R)-2,6-Dimethyl-8-hydroxy-2-octenoic acid 8-O-[6'-O-(E)-p-coumaroyl]-beta-D-glucopyranoside)