NP-MRD: Showing NP-Card for (2r,3r)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate (NP0290662)

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Record Information

Version

2.0

Created at

2022-09-09 21:26:51 UTC

Updated at

2022-09-09 21:26:52 UTC

NP-MRD ID

NP0290662

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate

Description

CHEMBL3105551 belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. (2r,3r)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate is found in Saururus chinensis. Based on a literature review very few articles have been published on CHEMBL3105551.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092223262D          

 34 35  0  0  1  0            999 V2000
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M  END

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  Mrv1652309092223262D          

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M  END
> <DATABASE_ID>
NP0290662

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CC=C)=CC(OC)=C1O[C@H](COC(C)=O)[C@H](O)C1=CC(OC)=C(OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O9/c1-8-9-16-10-18(28-3)25(19(11-16)29-4)34-22(14-33-15(2)26)23(27)17-12-20(30-5)24(32-7)21(13-17)31-6/h8,10-13,22-23,27H,1,9,14H2,2-7H3/t22-,23-/m1/s1

> <INCHI_KEY>
QQKYKRFSZPVBDT-DHIUTWEWSA-N

> <FORMULA>
C25H32O9

> <MOLECULAR_WEIGHT>
476.522

> <EXACT_MASS>
476.20463261

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
50.069029632029846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate

> <JCHEM_LOGP>
3.0307175986666675

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.295033894546545

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5445521745253403

> <JCHEM_POLAR_SURFACE_AREA>
101.91000000000003

> <JCHEM_REFRACTIVITY>
124.8136

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate

> <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       1.955   1.969   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.449   1.649   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.027   0.184   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.004  -0.961   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.510  -0.640   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.540  -1.785   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.047  -1.465   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.523  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.065  -3.249   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.095  -4.394   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.095  -5.934   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.761  -6.704   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.428  -5.934   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.094  -6.704   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.240  -5.934   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.094  -8.244   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.429  -6.704   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.429  -8.244   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.762  -5.934   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.762  -4.394   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.096  -3.624   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.096  -2.084   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.762  -1.314   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.430  -4.394   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.763  -3.624   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.097  -4.394   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.430  -5.934   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.763  -6.704   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      10.763  -8.244   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.096  -6.704   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.558  -3.570   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       1.082  -5.034   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.424  -5.354   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.528  -2.425   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   34                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10   31                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   11   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   30                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   19                                                       
CONECT   31    9   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34   31    4                                                       
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₉

Average Mass

476.5220 Da

Monoisotopic Mass

476.20463 Da

IUPAC Name

(2R,3R)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate

Traditional Name

(2R,3R)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(CC=C)=CC(OC)=C1O[C@H](COC(C)=O)[C@H](O)C1=CC(OC)=C(OC)C(OC)=C1

InChI Identifier

InChI=1S/C25H32O9/c1-8-9-16-10-18(28-3)25(19(11-16)29-4)34-22(14-33-15(2)26)23(27)17-12-20(30-5)24(32-7)21(13-17)31-6/h8,10-13,22-23,27H,1,9,14H2,2-7H3/t22-,23-/m1/s1

InChI Key

QQKYKRFSZPVBDT-DHIUTWEWSA-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
Saururus chinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Neolignan skeleton
M-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Alcohol
Organooxygen compound
Aromatic alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	3.03	ChemAxon
pKa (Strongest Acidic)	13.3	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	101.91 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	124.81 m³·mol⁻¹	ChemAxon
Polarizability	50.07 Å³	ChemAxon
Number of Rings	2	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

31126543

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76317428

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate (NP0290662)

MOL for NP0290662 ((2r,3r)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate)

3D MOL for NP0290662 ((2r,3r)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate)

3D SDF for NP0290662 ((2r,3r)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate)

3D-SDF for NP0290662 ((2r,3r)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate)

PDB for NP0290662 ((2r,3r)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate)

3D PDB for NP0290662 ((2r,3r)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate)

SMILES for NP0290662 ((2r,3r)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate)

INCHI for NP0290662 ((2r,3r)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate)

Structure for NP0290662 ((2r,3r)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate)

3D Structure for NP0290662 ((2r,3r)-2-[2,6-dimethoxy-4-(prop-2-en-1-yl)phenoxy]-3-hydroxy-3-(3,4,5-trimethoxyphenyl)propyl acetate)