MiMeDB: Showing metabocard for 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol (MMDBc0055095)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:41:58 UTC

Update Date

2022-08-12 20:09:13 UTC

Metabolite ID

MMDBc0055095

Metabolite Identification

Common Name

1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol

Description

10535-17-8, also known as VGBE, 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. Based on a literature review very few articles have been published on 10535-17-8.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221412D          

 24 25  0  0  0  0            999 V2000
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  2  0  0  0  0
 12  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13  6  2  0  0  0  0
 14  9  1  0  0  0  0
 15  7  2  0  0  0  0
 15 13  1  0  0  0  0
 16 10  1  0  0  0  0
 16 14  2  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 18 17  1  0  0  0  0
 19 11  1  0  0  0  0
 20 18  1  0  0  0  0
 21  1  1  0  0  0  0
 21 13  1  0  0  0  0
 22  2  1  0  0  0  0
 22 14  1  0  0  0  0
 23  3  1  0  0  0  0
 23 16  1  0  0  0  0
 24 15  1  0  0  0  0
 24 17  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0055095

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H22O6/c1-21-13-6-4-5-7-15(13)24-17(11-19)18(20)12-8-9-14(22-2)16(10-12)23-3/h4-10,17-20H,11H2,1-3H3

> <INCHI_KEY>
IEWUCQVFAWBYOC-UHFFFAOYSA-N

> <FORMULA>
C18H22O6

> <MOLECULAR_WEIGHT>
334.368

> <EXACT_MASS>
334.141638428

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.97920720496796

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol

> <JCHEM_LOGP>
1.8063639866666672

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.689464690586583

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.320775617728987

> <JCHEM_PKA_STRONGEST_BASIC>
-2.98976428720911

> <JCHEM_POLAR_SURFACE_AREA>
77.38000000000001

> <JCHEM_REFRACTIVITY>
88.44840000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  17.710   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335  13.860   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  15.400   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  16.170   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  15.400   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001  11.550   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667  13.860   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.667   9.240   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.001  16.170   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.001  13.090   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000  10.780   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3   23                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4   13                                                       
CONECT    7    5   15                                                       
CONECT    8    9   12                                                       
CONECT    9    8   14                                                       
CONECT   10   12   16                                                       
CONECT   11   17   19                                                       
CONECT   12    8   10   18                                                  
CONECT   13    6   15   21                                                  
CONECT   14    9   16   22                                                  
CONECT   15    7   13   24                                                  
CONECT   16   10   14   23                                                  
CONECT   17   11   18   24                                                  
CONECT   18   12   17   20                                                  
CONECT   19   11                                                            
CONECT   20   18                                                            
CONECT   21    1   13                                                       
CONECT   22    2   14                                                       
CONECT   23    3   16                                                       
CONECT   24   15   17                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

Synonyms

Value	Source
1-(3,4-Dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol	ChEBI
1-(4-O(14)CH3-3-Methoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol	MeSH
VGBE	MeSH
1-(3,4-Dimethoxyphenyl)-1,3-dihydroxy-2-(2-methoxyphenoxy)propane	MeSH
Veratrylglycerol-beta-guaiacyl ether	MeSH

Molecular Formula

C₁₈H₂₂O₆

Average Mass

334.368

Monoisotopic Mass

334.141638428

IUPAC Name

1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol

Traditional Name

1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C18H22O6/c1-21-13-6-4-5-7-15(13)24-17(11-19)18(20)12-8-9-14(22-2)16(10-12)23-3/h4-10,17-20H,11H2,1-3H3

InChI Key

IEWUCQVFAWBYOC-UHFFFAOYSA-N

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
O-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Ether
Aromatic alcohol
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Primary alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

diol (CHEBI:86963 )
dimethoxybenzene (CHEBI:86963 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	1.81	ChemAxon
pKa (Strongest Acidic)	13.32	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	77.38 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	88.45 m³·mol⁻¹	ChemAxon
Polarizability	34.98 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0016375	1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol	3,4-dimethoxybenzaldehyde	Ligninase-3	Depolymerization of lignin	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Basidiomycota	3	Human feces

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

167882

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

193461

PDB ID

Not Available

ChEBI ID

86963

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol (MMDBc0055095)

MOL for #<Metabolite:0x0000564af1d641c8>

3D MOL for #<Metabolite:0x0000564af1d641c8>

3D SDF for #<Metabolite:0x0000564af1d641c8>

3D-SDF for #<Metabolite:0x0000564af1d641c8>

PDB for #<Metabolite:0x0000564af1d641c8>

3D PDB for #<Metabolite:0x0000564af1d641c8>

SMILES for #<Metabolite:0x0000564af1d641c8>

INCHI for #<Metabolite:0x0000564af1d641c8>

Structure for #<Metabolite:0x0000564af1d641c8>

3D Structure for #<Metabolite:0x0000564af1d641c8>