NP-MRD: Showing NP-Card for [(2s,3r,4r)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2z)-2-methylbut-2-enoate (NP0193725)

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Record Information

Version

2.0

Created at

2022-09-04 11:15:44 UTC

Updated at

2022-09-04 11:15:44 UTC

NP-MRD ID

NP0193725

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2s,3r,4r)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2z)-2-methylbut-2-enoate

Description

SCHEMBL3684881 belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively. [(2s,3r,4r)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2z)-2-methylbut-2-enoate is found in Leontopodium alpinum. Based on a literature review very few articles have been published on SCHEMBL3684881.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042213152D          

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M  END

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 11 22  1  0  0  0  0
 10 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
  9 25  1  0  0  0  0
 25 26  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 33 36  2  0  0  0  0
 27 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0193725

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C[C@H]2CO[C@@H]([C@H]2COC(=O)C(\C)=C/C)C2=CC(OC)=C(OC)C(OC)=C2)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O8/c1-8-17(2)28(29)36-16-21-20(11-18-9-10-22(30-3)23(12-18)31-4)15-35-26(21)19-13-24(32-5)27(34-7)25(14-19)33-6/h8-10,12-14,20-21,26H,11,15-16H2,1-7H3/b17-8-/t20-,21-,26+/m0/s1

> <INCHI_KEY>
TZENRVOKDBSTKN-VDYKWYTQSA-N

> <FORMULA>
C28H36O8

> <MOLECULAR_WEIGHT>
500.588

> <EXACT_MASS>
500.241018119

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
55.01143984976471

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2S,3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
4.652364395999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.894081160042774

> <JCHEM_POLAR_SURFACE_AREA>
81.68000000000002

> <JCHEM_REFRACTIVITY>
136.45119999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.199  -0.115   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.199   1.425   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.134   2.195   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.134   3.735   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.468   1.425   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.802   2.195   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.468  -0.115   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.802  -0.885   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.802  -2.425   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.556  -3.330   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.091  -2.854   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.053  -3.885   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.518  -3.409   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.662  -4.439   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.127  -3.963   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.838  -1.903   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.303  -1.427   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.623   0.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.693  -0.872   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.014   0.634   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.478   1.110   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.771  -1.348   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       3.032  -4.795   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.572  -4.795   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.048  -3.330   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.512  -2.854   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.657  -3.885   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.121  -3.409   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.266  -4.439   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.946  -5.946   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      11.090  -6.976   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.555  -6.500   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.481  -6.422   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.161  -7.928   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.696  -8.404   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.337  -5.391   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   25                                                  
CONECT   10    9   11   23                                                  
CONECT   11   10   12   22                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   11                                                       
CONECT   23   10   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    9   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   36                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   27                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₆O₈

Average Mass

500.5880 Da

Monoisotopic Mass

500.24102 Da

IUPAC Name

[(2S,3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2Z)-2-methylbut-2-enoate

Traditional Name

[(2S,3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C[C@H]2CO[C@@H]([C@H]2COC(=O)C(\C)=C/C)C2=CC(OC)=C(OC)C(OC)=C2)C=C1OC

InChI Identifier

InChI=1S/C28H36O8/c1-8-17(2)28(29)36-16-21-20(11-18-9-10-22(30-3)23(12-18)31-4)15-35-26(21)19-13-24(32-5)27(34-7)25(14-19)33-6/h8-10,12-14,20-21,26H,11,15-16H2,1-7H3/b17-8-/t20-,21-,26+/m0/s1

InChI Key

TZENRVOKDBSTKN-VDYKWYTQSA-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
Leontopodium alpinum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7,9'-epoxylignans. These are lignans that contain the 7,9'-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

7,9'-epoxylignans

Alternative Parents

Substituents

7,9p-epoxylignan
Dimethoxybenzene
O-dimethoxybenzene
Methoxybenzene
Anisole
Phenoxy compound
Phenol ether
Fatty acid ester
Alkyl aryl ether
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Oxolane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	4.65	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	81.68 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	136.45 m³·mol⁻¹	ChemAxon
Polarizability	55.01 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

53302376

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2s,3r,4r)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2z)-2-methylbut-2-enoate (NP0193725)

MOL for NP0193725 ([(2s,3r,4r)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2z)-2-methylbut-2-enoate)

3D MOL for NP0193725 ([(2s,3r,4r)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2z)-2-methylbut-2-enoate)

3D SDF for NP0193725 ([(2s,3r,4r)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0193725 ([(2s,3r,4r)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2z)-2-methylbut-2-enoate)

PDB for NP0193725 ([(2s,3r,4r)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2z)-2-methylbut-2-enoate)

3D PDB for NP0193725 ([(2s,3r,4r)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2z)-2-methylbut-2-enoate)

SMILES for NP0193725 ([(2s,3r,4r)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2z)-2-methylbut-2-enoate)

INCHI for NP0193725 ([(2s,3r,4r)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2z)-2-methylbut-2-enoate)

Structure for NP0193725 ([(2s,3r,4r)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2z)-2-methylbut-2-enoate)

3D Structure for NP0193725 ([(2s,3r,4r)-4-[(3,4-dimethoxyphenyl)methyl]-2-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl (2z)-2-methylbut-2-enoate)