NP-MRD: Showing NP-Card for Geranyl butyrate (NP0049176)

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Record Information

Version

2.0

Created at

2022-03-17 21:08:19 UTC

Updated at

2022-03-17 21:08:19 UTC

NP-MRD ID

NP0049176

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Geranyl butyrate

Description

Neryl butyrate, also known as fema 2774 or nonyl N-butyrate, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Neryl butyrate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Neryl butyrate is a sweet, apple, and fruity tasting compound. Outside of the human body, Neryl butyrate has been detected, but not quantified in, several different foods, such as fruits, green vegetables, wild celeries, citrus, and garden tomato. This could make neryl butyrate a potential biomarker for the consumption of these foods. Geranyl butyrate is found in Artemisia absinthium, Bothriochloa bladhii, Cryptomeria japonica, Cymbopogon martinii, Foeniculum vulgare, Origanum syriacum, Pelargonium quercifolium, Schinus molle and Thymus citriodorus. Found in citrus peel oils, kumquat peel oil, celery leaves/stalks, tomato, yellow passion fruit, lavender oil and other essential oils.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 02241215192D          

 16 15  0  0  0  0            999 V2000
    2.1436    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8573    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4286    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049176

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H24O2/c1-5-7-14(15)16-11-10-13(4)9-6-8-12(2)3/h8,10H,5-7,9,11H2,1-4H3/b13-10-

> <INCHI_KEY>
ZSBOMYJPSRFZAL-RAXLEYEMSA-N

> <FORMULA>
C14H24O2

> <MOLECULAR_WEIGHT>
224.3392

> <EXACT_MASS>
224.177630012

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.627011299804128

> <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 butanoate

> <ALOGPS_LOGP>
5.07

> <JCHEM_LOGP>
4.088613218333333

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.043254283144128

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
69.56150000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.97e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.001   3.465   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   1.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.334   1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.335   1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.335   1.925   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.335   3.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -0.385   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.001  -1.155   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.001  -2.695   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.334  -3.465   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667  -3.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.335  -2.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -3.465   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
Neryl butyric acid	Generator
(Z)-3,7-Dimethyl-2,6-octadienyl butanoate	HMDB
(Z)-3,7-Dimethyl-2,6-octadienyl butyrate	HMDB
3,7-Dimethyl-2,6-octadienyl ester(Z)-butanoic acid	HMDB
3,7-Dimethyl-2,6-octadienyl ester(Z)-butyric acid	HMDB
3,7-Dimethyl-2,6-octadienyl esterz)-butanoic acid	HMDB
Butanoic acid, (2Z)-3,7-dimethyl-2,6-octadien-1-yl ester	HMDB
Butanoic acid, (2Z)-3,7-dimethyl-2,6-octadienyl ester	HMDB
cis-3,7-Dimethyl-2,6-octadienyl butanoate	HMDB
FEMA 2774	HMDB
Neryl butanoate	HMDB
Nonyl N-butyrate	HMDB
(Z)-3,7-Dimethyl-2,6-octadienyl butyric acid	Generator
Geranyl butyric acid	Generator

Chemical Formula

C₁₄H₂₄O₂

Average Mass

224.3392 Da

Monoisotopic Mass

224.17763 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

999-40-6

SMILES

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

InChI Identifier

InChI=1S/C14H24O2/c1-5-7-14(15)16-11-10-13(4)9-6-8-12(2)3/h8,10H,5-7,9,11H2,1-4H3/b13-10-

InChI Key

ZSBOMYJPSRFZAL-RAXLEYEMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apium graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Apium graveolens var. dulce	FooDB	Harvey J. Gold, Charles W. Wilson III The Volatile Flavor Substances of Celery. Journal of Food S...
Artemisia absinthium	LOTUS Database	35616633
Bothriochloa bladhii	LOTUS Database	35616633
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cryptomeria japonica	LOTUS Database	35616633
Cymbopogon martinii	LOTUS Database	35616633
Foeniculum vulgare	LOTUS Database	35616633
Origanum syriacum	LOTUS Database	35616633
Pelargonium quercifolium	LOTUS Database	35616633
Schinus molle	LOTUS Database	35616633
Solanum lycopersicum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Thymus citriodorus	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
Fatty acid ester
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

Wax monoesters (LMFA07010626 )

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	5.07	ALOGPS
logP	4.09	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-7	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	8	ChemAxon
Refractivity	69.56 m³·mol⁻¹	ChemAxon
Polarizability	27.63 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

HMDB0038259

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018005

KNApSAcK ID

Not Available

Chemspider ID

4509113

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5352162

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Geranyl butyrate (NP0049176)

MOL for NP0049176 (Geranyl butyrate)

3D MOL for NP0049176 (Geranyl butyrate)

3D SDF for NP0049176 (Geranyl butyrate)

3D-SDF for NP0049176 (Geranyl butyrate)

PDB for NP0049176 (Geranyl butyrate)

3D PDB for NP0049176 (Geranyl butyrate)

SMILES for NP0049176 (Geranyl butyrate)

INCHI for NP0049176 (Geranyl butyrate)

Structure for NP0049176 (Geranyl butyrate)

3D Structure for NP0049176 (Geranyl butyrate)