MiMeDB: Showing metabocard for N,N'-((1Z,3Z)-1,4-bis(4-methoxyphenyl)buta-1,3-diene-2,3-diyl)diformamide (MMDBc0008543)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 01:22:05 UTC

Update Date

2022-08-31 06:28:45 UTC

Metabolite ID

MMDBc0008543

Metabolite Identification

Common Name

N,N'-((1Z,3Z)-1,4-bis(4-methoxyphenyl)buta-1,3-diene-2,3-diyl)diformamide

Description

CHEBI:68205, also known as bis-MBDDF, 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 CHEBI:68205.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152103222D          

 28 29  0  0  0  0            999 V2000
   -3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 15  3  2  0  0  0  0
 15  4  1  0  0  0  0
 15 11  1  0  0  0  0
 16  5  2  0  0  0  0
 16  6  1  0  0  0  0
 16 12  1  0  0  0  0
 17  7  2  0  0  0  0
 17  8  1  0  0  0  0
 18  9  2  0  0  0  0
 18 10  1  0  0  0  0
 19 11  2  0  0  0  0
 20 12  2  0  0  0  0
 20 19  1  0  0  0  0
 21 13  2  0  0  0  0
 21 19  1  0  0  0  0
 22 14  2  0  0  0  0
 22 20  1  0  0  0  0
 13 23  1  4  0  0  0
 14 24  1  4  0  0  0
 25  1  1  0  0  0  0
 25 17  1  0  0  0  0
 26  2  1  0  0  0  0
 26 18  1  0  0  0  0
 27 11  1  0  0  0  0
 28 12  1  0  0  0  0
M  END


  Mrv1652305152103222D          

 28 29  0  0  0  0            999 V2000
   -3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 15  3  2  0  0  0  0
 15  4  1  0  0  0  0
 15 11  1  0  0  0  0
 16  5  2  0  0  0  0
 16  6  1  0  0  0  0
 16 12  1  0  0  0  0
 17  7  2  0  0  0  0
 17  8  1  0  0  0  0
 18  9  2  0  0  0  0
 18 10  1  0  0  0  0
 19 11  2  0  0  0  0
 20 12  2  0  0  0  0
 20 19  1  0  0  0  0
 21 13  2  0  0  0  0
 21 19  1  0  0  0  0
 22 14  2  0  0  0  0
 22 20  1  0  0  0  0
 13 23  1  4  0  0  0
 14 24  1  4  0  0  0
 25  1  1  0  0  0  0
 25 17  1  0  0  0  0
 26  2  1  0  0  0  0
 26 18  1  0  0  0  0
 27 11  1  0  0  0  0
 28 12  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0008543

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\N=CO)/C(/N=CO)=C(\[H])C1=CC=C(OC)C=C1)C1=CC=C(OC)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20N2O4/c1-25-17-7-3-15(4-8-17)11-19(21-13-23)20(22-14-24)12-16-5-9-18(26-2)10-6-16/h3-14H,1-2H3,(H,21,23)(H,22,24)/b19-11-,20-12-

> <INCHI_KEY>
ZRAIRHSUKMHHQT-YZLQMOBTSA-N

> <FORMULA>
C20H20N2O4

> <MOLECULAR_WEIGHT>
352.39

> <EXACT_MASS>
352.142307132

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
37.8016846351714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(1Z,3Z)-3-[(hydroxymethylidene)amino]-1,4-bis(4-methoxyphenyl)buta-1,3-dien-2-yl]carboximidic acid

> <ALOGPS_LOGP>
3.68

> <JCHEM_LOGP>
1.9346340547053154

> <ALOGPS_LOGS>
-5.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.9258893790759832

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0013857767684735

> <JCHEM_PKA_STRONGEST_BASIC>
4.6481505988663

> <JCHEM_POLAR_SURFACE_AREA>
83.64000000000001

> <JCHEM_REFRACTIVITY>
102.80739999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(1Z,3Z)-3-[(hydroxymethylidene)amino]-1,4-bis(4-methoxyphenyl)buta-1,3-dien-2-yl]carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      -6.668  11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      -8.002   4.620   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0      -5.335   1.540   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0     -10.669   4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -5.335  10.780   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0      -4.001   3.850   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      -9.336   2.310   0.000  0.00  0.00           H+0
CONECT    1   25                                                            
CONECT    2   26                                                            
CONECT    3    7   15                                                       
CONECT    4    8   15                                                       
CONECT    5    9   16                                                       
CONECT    6   10   16                                                       
CONECT    7    3   17                                                       
CONECT    8    4   17                                                       
CONECT    9    5   18                                                       
CONECT   10    6   18                                                       
CONECT   11   15   19   27                                                  
CONECT   12   16   20   28                                                  
CONECT   13   21   23                                                       
CONECT   14   22   24                                                       
CONECT   15    3    4   11                                                  
CONECT   16    5    6   12                                                  
CONECT   17    7    8   25                                                  
CONECT   18    9   10   26                                                  
CONECT   19   11   20   21                                                  
CONECT   20   12   19   22                                                  
CONECT   21   13   19                                                       
CONECT   22   14   20                                                       
CONECT   23   13                                                            
CONECT   24   14                                                            
CONECT   25    1   17                                                       
CONECT   26    2   18                                                       
CONECT   27   11                                                            
CONECT   28   12                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

Synonyms

Value	Source
N,N'-((1Z,3Z)-1,4-bis(4-methoxyphenyl)buta-1,3-diene-2,3-diyl)diformamide	MeSH
Bis-MBDDF	MeSH

Molecular Formula

C₂₀H₂₀N₂O₄

Average Mass

352.39

Monoisotopic Mass

352.142307132

IUPAC Name

N-[(1Z,3Z)-3-[(hydroxymethylidene)amino]-1,4-bis(4-methoxyphenyl)buta-1,3-dien-2-yl]carboximidic acid

Traditional Name

N-[(1Z,3Z)-3-[(hydroxymethylidene)amino]-1,4-bis(4-methoxyphenyl)buta-1,3-dien-2-yl]carboximidic acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\N=CO)/C(/N=CO)=C(\[H])C1=CC=C(OC)C=C1)C1=CC=C(OC)C=C1

InChI Identifier

InChI=1S/C20H20N2O4/c1-25-17-7-3-15(4-8-17)11-19(21-13-23)20(22-14-24)12-16-5-9-18(26-2)10-6-16/h3-14H,1-2H3,(H,21,23)(H,22,24)/b19-11-,20-12-

InChI Key

ZRAIRHSUKMHHQT-YZLQMOBTSA-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

Norlignan skeleton
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylpropanoid (CHEBI:68205 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0025 g/L	ALOGPS
logP	3.68	ALOGPS
logP	1.93	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	3	ChemAxon
pKa (Strongest Basic)	4.65	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.64 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	102.81 m³·mol⁻¹	ChemAxon
Polarizability	37.8 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

Not Available

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

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	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

9637136

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11462296

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for N,N'-((1Z,3Z)-1,4-bis(4-methoxyphenyl)buta-1,3-diene-2,3-diyl)diformamide (MMDBc0008543)

MOL for #<Metabolite:0x00007f922fd58ae0>

3D MOL for #<Metabolite:0x00007f922fd58ae0>

3D SDF for #<Metabolite:0x00007f922fd58ae0>

3D-SDF for #<Metabolite:0x00007f922fd58ae0>

PDB for #<Metabolite:0x00007f922fd58ae0>

3D PDB for #<Metabolite:0x00007f922fd58ae0>

SMILES for #<Metabolite:0x00007f922fd58ae0>

INCHI for #<Metabolite:0x00007f922fd58ae0>

Structure for #<Metabolite:0x00007f922fd58ae0>

3D Structure for #<Metabolite:0x00007f922fd58ae0>