NP-MRD: Showing NP-Card for Pseudoisoeugenol 2-methylbutanoate (NP0048255)

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Record Information

Version

2.0

Created at

2022-03-17 20:53:34 UTC

Updated at

2022-03-17 20:53:34 UTC

NP-MRD ID

NP0048255

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pseudoisoeugenol 2-methylbutanoate

Description

Pseudoisoeugenol 2-methylbutanoate 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. Pseudoisoeugenol 2-methylbutanoate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Pseudoisoeugenol 2-methylbutanoate has been detected, but not quantified in, a few different foods, such as anises, fats and oils, and herbs and spices. This could make pseudoisoeugenol 2-methylbutanoate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308312D          

 18 18  0  0  0  0            999 V2000
    4.2868   -3.3000    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
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    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
    2.8579   -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
    7.1447   -0.8250    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
    6.4302   -2.0625    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
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    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
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  5  2  0  0  0  0
  9  8  1  0  0  0  0
 11  3  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  2  0  0  0  0
 13  8  2  0  0  0  0
 13 10  1  0  0  0  0
 14  9  2  0  0  0  0
 14 12  1  0  0  0  0
 15 11  1  0  0  0  0
 16 15  2  0  0  0  0
 17  4  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048255

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)OC1=CC=C(OC)C=C1\C=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-5-7-12-10-13(17-4)8-9-14(12)18-15(16)11(3)6-2/h5,7-11H,6H2,1-4H3/b7-5+

> <INCHI_KEY>
YARRWVYKHJNVHX-FNORWQNLSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.216389779566512

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-2-[(1E)-prop-1-en-1-yl]phenyl 2-methylbutanoate

> <ALOGPS_LOGP>
4.69

> <JCHEM_LOGP>
4.234263377666668

> <ALOGPS_LOGS>
-4.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.817477441970196

> <JCHEM_POLAR_SURFACE_AREA>
35.53

> <JCHEM_REFRACTIVITY>
72.81580000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-2-[(1E)-prop-1-en-1-yl]phenyl 2-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       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.003  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      14.671  -3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3   11                                                            
CONECT    4   17                                                            
CONECT    5    1    7                                                       
CONECT    6    2   11                                                       
CONECT    7    5   12                                                       
CONECT    8    9   13                                                       
CONECT    9    8   14                                                       
CONECT   10   12   13                                                       
CONECT   11    3    6   15                                                  
CONECT   12    7   10   14                                                  
CONECT   13    8   10   17                                                  
CONECT   14    9   12   18                                                  
CONECT   15   11   16   18                                                  
CONECT   16   15                                                            
CONECT   17    4   13                                                       
CONECT   18   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
Pseudoisoeugenol 2-methylbutanoic acid	Generator
4-Methoxy-2-(prop-1-en-1-yl)phenyl 2-methylbutanoic acid	Generator

Chemical Formula

C₁₅H₂₀O₃

Average Mass

248.3175 Da

Monoisotopic Mass

248.14124 Da

IUPAC Name

4-methoxy-2-[(1E)-prop-1-en-1-yl]phenyl 2-methylbutanoate

Traditional Name

4-methoxy-2-[(1E)-prop-1-en-1-yl]phenyl 2-methylbutanoate

CAS Registry Number

58989-20-1

SMILES

CCC(C)C(=O)OC1=CC=C(OC)C=C1\C=C\C

InChI Identifier

InChI=1S/C15H20O3/c1-5-7-12-10-13(17-4)8-9-14(12)18-15(16)11(3)6-2/h5,7-11H,6H2,1-4H3/b7-5+

InChI Key

YARRWVYKHJNVHX-FNORWQNLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pimpinella anisum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Styrene
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	4.69	ALOGPS
logP	4.23	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-4.8	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	6	ChemAxon
Refractivity	72.82 m³·mol⁻¹	ChemAxon
Polarizability	28.22 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

HMDB0035503

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014192

KNApSAcK ID

Not Available

Chemspider ID

10229612

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14056365

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Pseudoisoeugenol 2-methylbutanoate (NP0048255)

MOL for NP0048255 (Pseudoisoeugenol 2-methylbutanoate)

3D MOL for NP0048255 (Pseudoisoeugenol 2-methylbutanoate)

3D SDF for NP0048255 (Pseudoisoeugenol 2-methylbutanoate)

3D-SDF for NP0048255 (Pseudoisoeugenol 2-methylbutanoate)

PDB for NP0048255 (Pseudoisoeugenol 2-methylbutanoate)

3D PDB for NP0048255 (Pseudoisoeugenol 2-methylbutanoate)

SMILES for NP0048255 (Pseudoisoeugenol 2-methylbutanoate)

INCHI for NP0048255 (Pseudoisoeugenol 2-methylbutanoate)

Structure for NP0048255 (Pseudoisoeugenol 2-methylbutanoate)

3D Structure for NP0048255 (Pseudoisoeugenol 2-methylbutanoate)