NP-MRD: Showing NP-Card for Geranyl 2-methylpropanoate (NP0049061)

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Record Information

Version

2.0

Created at

2022-03-17 21:06:30 UTC

Updated at

2022-03-17 21:06:30 UTC

NP-MRD ID

NP0049061

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Geranyl 2-methylpropanoate

Description

Geranyl 2-methylpropanoate, also known as fema 2513 or geranyl isobutanoate, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Geranyl 2-methylpropanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Geranyl 2-methylpropanoate is a sweet, apricot, and floral tasting compound. Outside of the human body, Geranyl 2-methylpropanoate is found, on average, in the highest concentration within wild carrots and carrots. Geranyl 2-methylpropanoate is found in Chamaemelum nobile, Cryptomeria japonica, Geigeria acaulis, Picradeniopsis multiflora and Pulicaria dysenterica. This could make geranyl 2-methylpropanoate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310192D          

 16 15  0  0  0  0            999 V2000
   -2.8579   -2.4750    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
    1.4289    0.8250    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
   -2.1434    1.2375    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
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 12  3  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13  8  1  0  0  0  0
 13  9  2  0  0  0  0
 14 12  1  0  0  0  0
 15 14  2  0  0  0  0
 16 10  1  0  0  0  0
 16 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049061

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H24O2/c1-11(2)7-6-8-13(5)9-10-16-14(15)12(3)4/h7,9,12H,6,8,10H2,1-5H3/b13-9-

> <INCHI_KEY>
OGJYXQFXLSCKTP-LCYFTJDESA-N

> <FORMULA>
C14H24O2

> <MOLECULAR_WEIGHT>
224.3392

> <EXACT_MASS>
224.177630012

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.318452487125445

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3,7-dimethylocta-2,6-dien-1-yl 2-methylpropanoate

> <ALOGPS_LOGP>
5.08

> <JCHEM_LOGP>
4.187030831666667

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.076150074502411

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
69.535

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.86e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3,7-dimethylocta-2,6-dien-1-yl 2-methylpropanoate

> <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      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5   13                                                            
CONECT    6    7    8                                                       
CONECT    7    6   11                                                       
CONECT    8    6   13                                                       
CONECT    9   10   13                                                       
CONECT   10    9   16                                                       
CONECT   11    1    2    7                                                  
CONECT   12    3    4   14                                                  
CONECT   13    5    8    9                                                  
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   10   14                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
Geranyl 2-methylpropanoic acid	Generator
(2Z)-3,7-Dimethyl-2,6-octadienyl 2-methylpropanoate	HMDB
(e)-3,7-Dimethyl-2,6-octadienyl 2-methylpropanoate	HMDB
(e)-3,7-Dimethyl-2,6-octadienyl isobutyrate	HMDB
3,7-Dimethyl-2,6-octadienyl estertrans-isobutyric acid	HMDB
3,7-Dimethyl-2,6-octadienyl isobutyrate	HMDB
3,7-Dimethyl-isobutyratetrans-2,6-octadien-1-ol	HMDB
FEMA 2513	HMDB
Geranyl isobutanoate	HMDB
Geranyl isobutyrate	HMDB
Isobutyric acid, (e)-3,7-dimethyl-2,6-octadienyl ester	HMDB
Neryl iso-butyrate	HMDB
trans-3,7-Dimethyl-2,6-octadien-1-yl 2-methylpropanoate	HMDB
trans-3,7-Dimethyl-2,6-octadien-1-yl isobutyrate	HMDB
trans-3-7-Dimethyl-2,6-octadienyl isobutyrate	HMDB

Chemical Formula

C₁₄H₂₄O₂

Average Mass

224.3392 Da

Monoisotopic Mass

224.17763 Da

IUPAC Name

(2Z)-3,7-dimethylocta-2,6-dien-1-yl 2-methylpropanoate

Traditional Name

(2Z)-3,7-dimethylocta-2,6-dien-1-yl 2-methylpropanoate

CAS Registry Number

2345-26-8

SMILES

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

InChI Identifier

InChI=1S/C14H24O2/c1-11(2)7-6-8-13(5)9-10-16-14(15)12(3)4/h7,9,12H,6,8,10H2,1-5H3/b13-9-

InChI Key

OGJYXQFXLSCKTP-LCYFTJDESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chamaemelum nobile	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Daucus carota	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Daucus carota ssp. sativus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Geigeria acaulis	LOTUS Database	35616633
Picradeniopsis multiflora	LOTUS Database	35616633
Pulicaria dysenterica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohol esters

Direct Parent

Fatty alcohol esters

Alternative Parents

Substituents

Fatty alcohol ester
Monoterpenoid
Acyclic monoterpenoid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	5.08	ALOGPS
logP	4.19	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	69.54 m³·mol⁻¹	ChemAxon
Polarizability	27.32 Å³	ChemAxon
Number of Rings	0	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

HMDB0038260

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017554

KNApSAcK ID

Not Available

Chemspider ID

4517923

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5365991

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Geranyl 2-methylpropanoate (NP0049061)

MOL for NP0049061 (Geranyl 2-methylpropanoate)

3D MOL for NP0049061 (Geranyl 2-methylpropanoate)

3D SDF for NP0049061 (Geranyl 2-methylpropanoate)

3D-SDF for NP0049061 (Geranyl 2-methylpropanoate)

PDB for NP0049061 (Geranyl 2-methylpropanoate)

3D PDB for NP0049061 (Geranyl 2-methylpropanoate)

SMILES for NP0049061 (Geranyl 2-methylpropanoate)

INCHI for NP0049061 (Geranyl 2-methylpropanoate)

Structure for NP0049061 (Geranyl 2-methylpropanoate)

3D Structure for NP0049061 (Geranyl 2-methylpropanoate)