NP-MRD: Showing NP-Card for Egonol (NP0047922)

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Record Information

Version

2.0

Created at

2022-03-17 20:48:08 UTC

Updated at

2022-03-17 20:48:08 UTC

NP-MRD ID

NP0047922

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Egonol

Description

Egonol belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Egonol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Egonol has been detected, but not quantified in, mushrooms. Egonol is found in Garcinia mangostana, Laetiporus sulphureus, Laetiporus sulphureus var.miniatus , Styrax agrestis, Styrax camporum, Styrax ferrugineus, Styrax japonicus and Styrax officinalis. Egonol was first documented in 2004 (PMID: 15643559). This could make egonol a potential biomarker for the consumption of these foods (PMID: 21939219) (PMID: 16206040).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307412D          

 24 27  0  0  0  0            999 V2000
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9966    0.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1034    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6909    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279    1.1104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9104    1.3514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2430    0.1954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13  4  1  0  0  0  0
 13  9  2  0  0  0  0
 14  7  1  0  0  0  0
 14 10  1  0  0  0  0
 15  5  1  0  0  0  0
 16 10  2  0  0  0  0
 16 13  1  0  0  0  0
 17  9  1  0  0  0  0
 17 15  2  0  0  0  0
 18  8  2  0  0  0  0
 19 14  2  0  0  0  0
 19 18  1  0  0  0  0
 20  6  1  0  0  0  0
 21  1  1  0  0  0  0
 21 18  1  0  0  0  0
 22 11  1  0  0  0  0
 22 15  1  0  0  0  0
 23 11  1  0  0  0  0
 23 17  1  0  0  0  0
 24 16  1  0  0  0  0
 24 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047922

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(CCCO)=CC2=C1OC(=C2)C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O5/c1-21-18-8-12(3-2-6-20)7-14-10-16(24-19(14)18)13-4-5-15-17(9-13)23-11-22-15/h4-5,7-10,20H,2-3,6,11H2,1H3

> <INCHI_KEY>
VOLZBKQSLGCZGC-UHFFFAOYSA-N

> <FORMULA>
C19H18O5

> <MOLECULAR_WEIGHT>
326.3432

> <EXACT_MASS>
326.115423686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.17358805430644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[2-(2H-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propan-1-ol

> <ALOGPS_LOGP>
3.61

> <JCHEM_LOGP>
3.131038006999999

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.963383224945375

> <JCHEM_PKA_STRONGEST_BASIC>
-2.377416177408894

> <JCHEM_POLAR_SURFACE_AREA>
61.06

> <JCHEM_REFRACTIVITY>
88.3148

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[2-(2H-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propan-1-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.197   6.693   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.483   4.176   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.023   4.176   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.865   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.483   1.509   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.460   0.991   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.793   2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.023   1.509   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.199   2.073   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -7.299   2.523   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.054   0.365   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    3    6                                                       
CONECT    3    2   12                                                       
CONECT    4    5   13                                                       
CONECT    5    4   15                                                       
CONECT    6    2   20                                                       
CONECT    7   12   14                                                       
CONECT    8   12   18                                                       
CONECT    9   13   17                                                       
CONECT   10   14   16                                                       
CONECT   11   22   23                                                       
CONECT   12    3    7    8                                                  
CONECT   13    4    9   16                                                  
CONECT   14    7   10   19                                                  
CONECT   15    5   17   22                                                  
CONECT   16   10   13   24                                                  
CONECT   17    9   15   23                                                  
CONECT   18    8   19   21                                                  
CONECT   19   14   18   24                                                  
CONECT   20    6                                                            
CONECT   21    1   18                                                       
CONECT   22   11   15                                                       
CONECT   23   11   17                                                       
CONECT   24   16   19                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Value	Source
2-(1,3-Benzodioxol-5-yl)-7-methoxy-5-benzofuranpropanol	ChEBI
2-(1,3-Benzodioxol-5-yl)-7-methoxy-5-benzofuranpropanol, 9ci	HMDB
5-(2-Hydroxypropyl)-7-methoxy-2-(3,4-methylenedioxyphenyl)benzofuran	HMDB
Isolated from leaves OF styrax ferrugineus	HMDB

Chemical Formula

C₁₉H₁₈O₅

Average Mass

326.3432 Da

Monoisotopic Mass

326.11542 Da

IUPAC Name

3-[2-(2H-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propan-1-ol

Traditional Name

3-[2-(2H-1,3-benzodioxol-5-yl)-7-methoxy-1-benzofuran-5-yl]propan-1-ol

CAS Registry Number

530-22-3

SMILES

COC1=CC(CCCO)=CC2=C1OC(=C2)C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C19H18O5/c1-21-18-8-12(3-2-6-20)7-14-10-16(24-19(14)18)13-4-5-15-17(9-13)23-11-22-15/h4-5,7-10,20H,2-3,6,11H2,1H3

InChI Key

VOLZBKQSLGCZGC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Garcinia mangostana	LOTUS Database	35616633
Laetiporus sulphureus	LOTUS Database	35616633
Laetiporus sulphureus var.miniatus	Fungi	KNApSAcK
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Styrax agrestis	LOTUS Database	35616633
Styrax camporum	LOTUS Database	35616633
Styrax ferrugineus	LOTUS Database	35616633
Styrax japonicus	LOTUS Database	35616633
Styrax officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Neolignan skeleton
Benzodioxole
Benzofuran
Anisole
Alkyl aryl ether
Benzenoid
Furan
Heteroaromatic compound
Organoheterocyclic compound
Ether
Oxacycle
Acetal
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

aromatic ether (CHEBI:69558 )
1-benzofurans (CHEBI:69558 )
benzodioxoles (CHEBI:69558 )
primary alcohol (CHEBI:69558 )

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	3.61	ALOGPS
logP	3.13	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	15.96	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	61.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	88.31 m³·mol⁻¹	ChemAxon
Polarizability	36.17 Å³	ChemAxon
Number of Rings	4	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

HMDB0034279

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012616

KNApSAcK ID

C00032931

Chemspider ID

425433

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

485186

PDB ID

Not Available

ChEBI ID

69558

Good Scents ID

Not Available

References

General References

Liu J, Dumontet V, Simonin AL, Iorga BI, Guerineau V, Litaudon M, Nguyen VH, Gueritte F: Benzofurans from Styrax agrestis as acetylcholinesterase inhibitors: structure-activity relationships and molecular modeling studies. J Nat Prod. 2011 Oct 28;74(10):2081-8. doi: 10.1021/np200308j. Epub 2011 Sep 22. [PubMed:21939219 ]
Min BS, Oh SR, Ahn KS, Kim JH, Lee J, Kim DY, Kim EH, Lee HK: Anti-complement activity of norlignans and terpenes from the stem bark of Styrax japonica. Planta Med. 2004 Dec;70(12):1210-5. doi: 10.1055/s-2004-835853. [PubMed:15643559 ]
Li QL, Li BG, Qi HY, Gao XP, Zhang GL: Four new benzofurans from seeds of Styrax perkinsiae. Planta Med. 2005 Sep;71(9):847-51. doi: 10.1055/s-2005-871226. [PubMed:16206040 ]

Showing NP-Card for Egonol (NP0047922)

MOL for NP0047922 (Egonol)

3D MOL for NP0047922 (Egonol)

3D SDF for NP0047922 (Egonol)

3D-SDF for NP0047922 (Egonol)

PDB for NP0047922 (Egonol)

3D PDB for NP0047922 (Egonol)

SMILES for NP0047922 (Egonol)

INCHI for NP0047922 (Egonol)

Structure for NP0047922 (Egonol)

3D Structure for NP0047922 (Egonol)