NP-MRD: Showing NP-Card for Wyerone epoxide (NP0046075)

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Record Information

Version

2.0

Created at

2022-03-17 19:47:58 UTC

Updated at

2022-03-17 19:47:58 UTC

NP-MRD ID

NP0046075

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Wyerone epoxide

Description

Wyerone epoxide belongs to the class of organic compounds known as furanoid fatty acids. These are fatty acids containing a 5-alkylfuran-2-alkanoic acid. Wyerone epoxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Wyerone epoxide has been detected, but not quantified in, broad beans and pulses. This could make wyerone epoxide a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305372D          

 20 21  0  0  0  0            999 V2000
    4.6972   -3.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9838    1.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6972   -2.7941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5500    1.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6270    2.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5702   -0.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1021    0.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5702   -0.8421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8065    3.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9625    2.2124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5702    0.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9827   -2.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8557    1.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5702   -1.6671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3216    2.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2847    1.2204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6571    1.6312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4989    2.4711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7695    2.0409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1577   -2.3816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  7  4  1  0  0  0  0
  8  6  3  0  0  0  0
  9  5  2  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  3  1  0  0  0  0
 13  7  2  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 14 12  1  0  0  0  0
 15  9  1  0  0  0  0
 16 11  2  0  0  0  0
 17 15  2  0  0  0  0
 18  2  1  0  0  0  0
 18 15  1  0  0  0  0
 19 10  1  0  0  0  0
 19 13  1  0  0  0  0
 20 12  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046075

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1OC1C#CC(=O)C1=CC=C(O1)\C=C/C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c1-3-12-14(20-12)8-6-11(16)13-7-4-10(19-13)5-9-15(17)18-2/h4-5,7,9,12,14H,3H2,1-2H3/b9-5-

> <INCHI_KEY>
FRIBCHAVILXSND-UITAMQMPSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.001609552018465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2Z)-3-{5-[3-(3-ethyloxiran-2-yl)prop-2-ynoyl]furan-2-yl}prop-2-enoate

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.4846493696666667

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.508246585496206

> <JCHEM_PKA_STRONGEST_BASIC>
-4.024818541255091

> <JCHEM_POLAR_SURFACE_AREA>
69.04

> <JCHEM_REFRACTIVITY>
72.31119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2Z)-3-{5-[3-(3-ethyloxiran-2-yl)prop-2-ynoyl]furan-2-yl}prop-2-enoate

> <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       8.768  -6.756   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.836   3.367   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.768  -5.216   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.893   2.796   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.037   5.537   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.664  -0.032   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.924   1.652   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.664  -1.572   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.505   5.698   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.663   4.130   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.664   1.508   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.434  -4.446   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.331   2.278   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.664  -3.112   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.600   4.452   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.998   2.278   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.227   3.045   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.931   4.613   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.170   3.810   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.894  -4.446   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   18                                                            
CONECT    3    1   12                                                       
CONECT    4    7   10                                                       
CONECT    5    9   10                                                       
CONECT    6    8   11                                                       
CONECT    7    4   13                                                       
CONECT    8    6   14                                                       
CONECT    9    5   15                                                       
CONECT   10    4    5   19                                                  
CONECT   11    6   13   16                                                  
CONECT   12    3   14   20                                                  
CONECT   13    7   11   19                                                  
CONECT   14    8   12   20                                                  
CONECT   15    9   17   18                                                  
CONECT   16   11                                                            
CONECT   17   15                                                            
CONECT   18    2   15                                                       
CONECT   19   10   13                                                       
CONECT   20   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2Z)-3-{5-[3-(3-ethyloxiran-2-yl)prop-2-ynoyl]furan-2-yl}prop-2-enoic acid	Generator

Chemical Formula

C₁₅H₁₄O₅

Average Mass

274.2687 Da

Monoisotopic Mass

274.08412 Da

IUPAC Name

methyl (2Z)-3-{5-[3-(3-ethyloxiran-2-yl)prop-2-ynoyl]furan-2-yl}prop-2-enoate

Traditional Name

methyl (2Z)-3-{5-[3-(3-ethyloxiran-2-yl)prop-2-ynoyl]furan-2-yl}prop-2-enoate

CAS Registry Number

60375-16-8

SMILES

CCC1OC1C#CC(=O)C1=CC=C(O1)\C=C/C(=O)OC

InChI Identifier

InChI=1S/C15H14O5/c1-3-12-14(20-12)8-6-11(16)13-7-4-10(19-13)5-9-15(17)18-2/h4-5,7,9,12,14H,3H2,1-2H3/b9-5-

InChI Key

FRIBCHAVILXSND-UITAMQMPSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Vicia faba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoid fatty acids. These are fatty acids containing a 5-alkylfuran-2-alkanoic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Furanoid fatty acids

Alternative Parents

Substituents

Furanoid fatty acid
Aryl ketone
Fatty acid ester
Heteroaromatic compound
Furan
Alpha,beta-unsaturated ketone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	2.26	ALOGPS
logP	2.48	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	18.51	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.04 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	72.31 m³·mol⁻¹	ChemAxon
Polarizability	28 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

External Links

HMDB ID

HMDB0030949

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002926

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

131751106

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Wyerone epoxide (NP0046075)

MOL for NP0046075 (Wyerone epoxide)

3D MOL for NP0046075 (Wyerone epoxide)

3D SDF for NP0046075 (Wyerone epoxide)

3D-SDF for NP0046075 (Wyerone epoxide)

PDB for NP0046075 (Wyerone epoxide)

3D PDB for NP0046075 (Wyerone epoxide)

SMILES for NP0046075 (Wyerone epoxide)

INCHI for NP0046075 (Wyerone epoxide)

Structure for NP0046075 (Wyerone epoxide)

3D Structure for NP0046075 (Wyerone epoxide)