NP-MRD: Showing NP-Card for [4-(hydroxymethyl)-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate (NP0164243)

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Record Information

Version

2.0

Created at

2022-09-02 23:05:16 UTC

Updated at

2022-09-02 23:05:16 UTC

NP-MRD ID

NP0164243

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[4-(hydroxymethyl)-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate

Description

[4-(Hydroxymethyl)-2-(7-methoxy-2H-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate belongs to the class of organic compounds known as 7,7'-epoxylignans. These are lignans with a structure based on a 2,5-diaryl-3, 4-dimethyltetrahydrofuran skeleton. [4-(hydroxymethyl)-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate is found in Peperomia leptostachya. [4-(Hydroxymethyl)-2-(7-methoxy-2H-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161521092D          

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M  END

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  Mrv1533004161521092D          

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M  END
> <DATABASE_ID>
NP0164243

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OCOC2=CC(=C1)C1OC(C(CO)C1COC(C)=O)C1=CC(OC)=C(OC)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O10/c1-13(27)32-11-17-16(10-26)22(14-6-18(28-2)24(31-5)19(7-14)29-3)35-23(17)15-8-20(30-4)25-21(9-15)33-12-34-25/h6-9,16-17,22-23,26H,10-12H2,1-5H3

> <INCHI_KEY>
XVJHXVOMXKSXLD-UHFFFAOYSA-N

> <FORMULA>
C25H30O10

> <MOLECULAR_WEIGHT>
490.505

> <EXACT_MASS>
490.183897166

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
50.72906913936411

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[4-(hydroxymethyl)-2-(7-methoxy-2H-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate

> <ALOGPS_LOGP>
2.35

> <JCHEM_LOGP>
1.4722029650000001

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.3598348725133

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6414082267626826

> <JCHEM_POLAR_SURFACE_AREA>
111.14000000000001

> <JCHEM_REFRACTIVITY>
122.49330000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[4-(hydroxymethyl)-2-(7-methoxy-2H-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      15.876   1.604   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      14.344   1.765   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      13.718   3.172   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.187   3.333   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.560   4.740   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.465   5.986   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.997   5.825   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      14.902   7.071   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      16.434   6.910   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.623   4.418   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      16.155   4.257   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      17.060   5.503   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.029   4.901   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.998   3.756   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.752   5.914   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.608   6.945   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.928   8.451   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.784   9.482   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.319   9.006   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.104  10.988   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.259   6.235   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.885   7.641   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.417   7.802   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.258  -1.007   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    5   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   16   13   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   15   26   35                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   30   35                                                  
CONECT   35   34   25                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
[4-(Hydroxymethyl)-2-(7-methoxy-2H-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetic acid	Generator

Chemical Formula

C₂₅H₃₀O₁₀

Average Mass

490.5050 Da

Monoisotopic Mass

490.18390 Da

IUPAC Name

[4-(hydroxymethyl)-2-(7-methoxy-2H-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate

Traditional Name

[4-(hydroxymethyl)-2-(7-methoxy-2H-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

COC1=C2OCOC2=CC(=C1)C1OC(C(CO)C1COC(C)=O)C1=CC(OC)=C(OC)C(OC)=C1

InChI Identifier

InChI=1S/C25H30O10/c1-13(27)32-11-17-16(10-26)22(14-6-18(28-2)24(31-5)19(7-14)29-3)35-23(17)15-8-20(30-4)25-21(9-15)33-12-34-25/h6-9,16-17,22-23,26H,10-12H2,1-5H3

InChI Key

XVJHXVOMXKSXLD-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
Peperomia leptostachya	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7,7'-epoxylignans. These are lignans with a structure based on a 2,5-diaryl-3, 4-dimethyltetrahydrofuran skeleton.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Furanoid lignans

Sub Class

Tetrahydrofuran lignans

Direct Parent

7,7'-epoxylignans

Alternative Parents

Substituents

7,7p-epoxylignan
Dibenzylbutane lignan skeleton
Benzodioxole
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Tetrahydrofuran
Carboxylic acid ester
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Oxacycle
Ether
Monocarboxylic acid or derivatives
Carbonyl group
Primary alcohol
Organic oxygen compound
Organic oxide
Alcohol
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	2.35	ALOGPS
logP	1.47	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	15.36	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.14 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	122.49 m³·mol⁻¹	ChemAxon
Polarizability	50.73 Å³	ChemAxon
Number of Rings	4	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

73065854

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [4-(hydroxymethyl)-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate (NP0164243)

MOL for NP0164243 ([4-(hydroxymethyl)-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate)

3D MOL for NP0164243 ([4-(hydroxymethyl)-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate)

3D SDF for NP0164243 ([4-(hydroxymethyl)-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate)

3D-SDF for NP0164243 ([4-(hydroxymethyl)-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate)

PDB for NP0164243 ([4-(hydroxymethyl)-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate)

3D PDB for NP0164243 ([4-(hydroxymethyl)-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate)

SMILES for NP0164243 ([4-(hydroxymethyl)-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate)

INCHI for NP0164243 ([4-(hydroxymethyl)-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate)

Structure for NP0164243 ([4-(hydroxymethyl)-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate)

3D Structure for NP0164243 ([4-(hydroxymethyl)-2-(7-methoxy-2h-1,3-benzodioxol-5-yl)-5-(3,4,5-trimethoxyphenyl)oxolan-3-yl]methyl acetate)