NP-MRD: Showing NP-Card for eugenol isovalerate (NP0261151)

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Record Information

Version

2.0

Created at

2022-09-08 03:31:15 UTC

Updated at

2022-09-08 03:31:15 UTC

NP-MRD ID

NP0261151

Secondary Accession Numbers

None

Natural Product Identification

Common Name

eugenol isovalerate

Description

Eugenyl isovalerate belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. Eugenyl isovalerate is an extremely weak basic (essentially neutral) compound (based on its pKa). Eugenyl isovalerate is a clove and fruity tasting compound. Outside of the human body,. Eugenyl isovalerate is used as a food additive ("EAFUS: Everything Added to Food in the United States. eugenol isovalerate is found in Felicia uliginosa and Valeriana officinalis. ").

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 38  0  0  0  0  0  0  0  0999 V2000
    5.9410    2.0142    0.2609 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2189    0.9336   -0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2348    0.8873   -1.1108 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9103    0.6016   -0.5126 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1325    1.6669   -0.1226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8971    1.4281    0.4362 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4149    0.1517    0.6171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8344   -0.0413    1.1837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9578   -0.1039    0.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8070    0.0182   -0.8550 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2971   -0.3062    0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3812   -0.3457   -0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5020    0.9020   -0.9012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7038   -0.5278    0.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1935   -0.9117    0.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7634   -2.2122    0.3831 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5934   -3.2769   -0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4285   -0.6753   -0.3319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7981    2.9043   -0.3676 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6520    2.0693    1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3822    0.0652    0.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5010    0.1391   -1.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2151    1.9094   -1.5702 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4612    2.6865   -0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2939    2.2968    0.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3245   -1.2752    1.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5048    0.4739    1.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2540   -1.2223   -0.7506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4543    1.7892   -0.2211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7725    0.9628   -1.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5308    0.9231   -1.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3890   -1.1674    0.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5600   -0.9927    1.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2313    0.4316    0.8010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5664   -3.2173    0.4749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7782   -3.2193   -1.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0672   -4.2421    0.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0610   -1.5177   -0.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 15  1  0
 15  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  4 18  2  0
 18 15  1  0
 17 35  1  0
 17 36  1  0
 17 37  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
  6 25  1  0
  5 24  1  0
  3 22  1  0
  3 23  1  0
  2 21  1  0
  1 19  1  0
  1 20  1  0
 18 38  1  0
M  END


  Mrv0541 05061307362D          

 18 18  0  0  0  0            999 V2000
    8.5737    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    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
    6.4302   -0.4125    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
    5.7158   -1.6500    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
    3.5724   -0.4125    0.0000 O   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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  6  5  1  0  0  0  0
  8  7  2  0  0  0  0
 11  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  9  1  0  0  0  0
 12  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  2  0  0  0  0
 13  8  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  2  0  0  0  0
 15  9  1  0  0  0  0
 16 15  2  0  0  0  0
 17  4  1  0  0  0  0
 17 14  1  0  0  0  0
 18 13  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0261151

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-5-6-12-7-8-13(14(10-12)17-4)18-15(16)9-11(2)3/h5,7-8,10-11H,1,6,9H2,2-4H3

> <INCHI_KEY>
PLUVLWUSXQCTNH-UHFFFAOYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.812740551114082

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methoxy-4-(prop-2-en-1-yl)phenyl 3-methylbutanoate

> <ALOGPS_LOGP>
4.36

> <JCHEM_LOGP>
3.9535298659999993

> <ALOGPS_LOGS>
-4.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.901945443212535

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
71.71740000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.35e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methoxy-4-(prop-2-en-1-yl)phenyl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
1

$$$$

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      16.004   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.671  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.337   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.669  -4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4   17                                                            
CONECT    5    1    6                                                       
CONECT    6    5   12                                                       
CONECT    7    8   12                                                       
CONECT    8    7   13                                                       
CONECT    9   11   15                                                       
CONECT   10   12   14                                                       
CONECT   11    2    3    9                                                  
CONECT   12    6    7   10                                                  
CONECT   13    8   14   18                                                  
CONECT   14   10   13   17                                                  
CONECT   15    9   16   18                                                  
CONECT   16   15                                                            
CONECT   17    4   14                                                       
CONECT   18   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
Eugenyl isovaleric acid	Generator
4-Allyl-2-methoxyphenyl isovalerate	HMDB
S-(3-Methylbutanoyl)-dihydrolipoamide	HMDB
2-Methoxy-4-(prop-2-en-1-yl)phenyl 3-methylbutanoic acid	Generator

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3175 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

2-methoxy-4-(prop-2-en-1-yl)phenyl 3-methylbutanoate

Traditional Name

2-methoxy-4-(prop-2-en-1-yl)phenyl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H20O3/c1-5-6-12-7-8-13(14(10-12)17-4)18-15(16)9-11(2)3/h5,7-8,10-11H,1,6,9H2,2-4H3

InChI Key

PLUVLWUSXQCTNH-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
Felicia uliginosa	LOTUS Database	35616633
Valeriana officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol esters

Alternative Parents

Substituents

Phenol ester
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Carboxylic acid ester
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	4.36	ALOGPS
logP	3.95	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	71.72 m³·mol⁻¹	ChemAxon
Polarizability	27.81 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0034123

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012394

KNApSAcK ID

Not Available

Chemspider ID

2342161

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3085213

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for eugenol isovalerate (NP0261151)

MOL for NP0261151 (eugenol isovalerate)

3D MOL for NP0261151 (eugenol isovalerate)

3D SDF for NP0261151 (eugenol isovalerate)

3D-SDF for NP0261151 (eugenol isovalerate)

PDB for NP0261151 (eugenol isovalerate)

3D PDB for NP0261151 (eugenol isovalerate)

SMILES for NP0261151 (eugenol isovalerate)

INCHI for NP0261151 (eugenol isovalerate)

Structure for NP0261151 (eugenol isovalerate)

3D Structure for NP0261151 (eugenol isovalerate)