NP-MRD: Showing NP-Card for (2z)-3,7-dimethylocta-2,6-dien-1-yl hexanoate (NP0183156)

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Record Information

Version

2.0

Created at

2022-09-03 22:00:49 UTC

Updated at

2022-09-03 22:00:49 UTC

NP-MRD ID

NP0183156

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z)-3,7-dimethylocta-2,6-dien-1-yl hexanoate

Description

Geranyl hexanoate, also known as fema 2515 or geranyl caproate, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Geranyl hexanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Geranyl hexanoate is a fruity, geranium, and rose tasting compound. Outside of the human body, Geranyl hexanoate has been detected, but not quantified in, citrus and fruits. (2z)-3,7-dimethylocta-2,6-dien-1-yl hexanoate is found in Schinus molle. This could make geranyl hexanoate a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 45  0  0  0  0  0  0  0  0999 V2000
    7.2136    0.3698    1.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3574    0.7380   -0.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2112   -0.2745   -0.2588 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3952   -0.2485    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2317   -1.1747    1.0357 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2495   -0.8593   -0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4645    0.1362   -0.7588 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1089   -1.6320   -0.2264 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2145   -1.2433   -1.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3398    0.0970   -1.0014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6329    0.3792   -0.8547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9598    1.8292   -0.5748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7139   -0.6092   -0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5164   -0.8232    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2288    0.3335    0.7857 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5790    0.3387    0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2893    1.5016    1.3882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3595   -0.8336    0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0229   -0.6644    1.3721 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0350    1.0266    1.9559 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2792    0.4227    0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9235    0.8217   -1.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9168    1.7375    0.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6818   -0.0036   -1.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6943   -1.2664   -0.4365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0545    0.8231    1.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0657   -0.3878    1.8915 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7726   -1.1871    2.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5397   -2.2479    0.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5356   -2.0296   -1.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431   -1.2015   -2.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3530    0.9583   -0.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2740    2.4214   -1.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9764    2.0723   -0.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6881    2.1222    0.4536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3837   -0.2478   -1.8443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3385   -1.5789   -1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2140   -1.6957    0.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8060   -1.2117    1.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7135    1.2003    1.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5477    1.3245    2.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6069    2.3791    1.3793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1827    1.7979    0.7988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4214   -0.5569    0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2982   -1.6967    1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0226   -1.1563   -0.6662 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  3
 16 17  1  0
 16 18  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
M  END


  Mrv0541 02241217112D          

 18 17  0  0  0  0            999 V2000
    3.5723    1.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5723    1.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2873    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7151    1.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7151    1.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4286    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436    1.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8573    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001    0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150   -0.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150   -1.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001   -1.8570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -1.8556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -1.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573   -1.8570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5723   -1.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2873   -1.8570    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  8  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  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
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0183156

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H28O2/c1-5-6-7-11-16(17)18-13-12-15(4)10-8-9-14(2)3/h9,12H,5-8,10-11,13H2,1-4H3/b15-12-

> <INCHI_KEY>
ARVSCQUZFFSNKF-QINSGFPZSA-N

> <FORMULA>
C16H28O2

> <MOLECULAR_WEIGHT>
252.3923

> <EXACT_MASS>
252.20893014

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
31.756960139431207

> <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 hexanoate

> <ALOGPS_LOGP>
5.90

> <JCHEM_LOGP>
4.977750548333333

> <ALOGPS_LOGS>
-4.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.043362495161395

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
78.76350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e-02 g/l

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

> <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       6.668   3.466   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   1.926   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.003   1.156   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.335   3.466   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.335   1.926   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.156   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   1.926   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.334   1.156   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.156   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -0.384   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.335  -1.154   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.335  -2.696   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000  -3.466   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667  -3.464   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001  -2.696   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.334  -3.466   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.668  -2.696   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.003  -3.466   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2                                                            
CONECT    4    5                                                            
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    2    7                                                       
CONECT    9    5   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   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
Geranyl hexanoic acid	Generator
(2E)-3,7-Dimethyl-2,6-octadienyl hexanoate	HMDB
(e)-3,7-Dimethyl-2,6-octadienyl hexanoate	HMDB
(e)-3,7-Dimethylocta-2,6-dien-1-yl N-hexanoate	HMDB
3,7-Dimethyl-2,6-octadienyl ester(e)-hexanoic acid	HMDB
3,7-Dimethyl-hexanoate(e)-2,6-octadien-1-ol	HMDB
3,7-Dimethylocta-2,6-dien-1-yl ester(e)-hexanoic acid	HMDB
FEMA 2515	HMDB
Geranyl caproate	HMDB
Geranyl N-hexanoate	HMDB
Hexanoic acid, (2E)-3,7-dimethyl-2,6-octadien-1-yl ester	HMDB
Hexanoic acid, (2E)-3,7-dimethyl-2,6-octadienyl ester	HMDB
Hexanoic acid, (2Z)-3,7-dimethyl-2,6-octadien-1-yl ester	HMDB
Hexanoic acid, (2Z)-3,7-dimethyl-2,6-octadienyl ester	HMDB
Neryl caproate	HMDB
Neryl hexanoate	HMDB
trans-3,7-Dimethyl-2,6-octadien-1-yl hexanoate	HMDB
(Z)-3,7-Dimethyl-2,6-octadienyl hexanoic acid	Generator

Chemical Formula

C₁₆H₂₈O₂

Average Mass

252.3923 Da

Monoisotopic Mass

252.20893 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H28O2/c1-5-6-7-11-16(17)18-13-12-15(4)10-8-9-14(2)3/h9,12H,5-8,10-11,13H2,1-4H3/b15-12-

InChI Key

ARVSCQUZFFSNKF-QINSGFPZSA-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
Schinus molle	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 (LMFA07010627 )

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	5.9	ALOGPS
logP	4.98	ChemAxon
logS	-4.3	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	10	ChemAxon
Refractivity	78.76 m³·mol⁻¹	ChemAxon
Polarizability	31.76 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

HMDB0029351

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000412

KNApSAcK ID

Not Available

Chemspider ID

20122200

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12571389

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z)-3,7-dimethylocta-2,6-dien-1-yl hexanoate (NP0183156)

MOL for NP0183156 ((2z)-3,7-dimethylocta-2,6-dien-1-yl hexanoate)

3D MOL for NP0183156 ((2z)-3,7-dimethylocta-2,6-dien-1-yl hexanoate)

3D SDF for NP0183156 ((2z)-3,7-dimethylocta-2,6-dien-1-yl hexanoate)

3D-SDF for NP0183156 ((2z)-3,7-dimethylocta-2,6-dien-1-yl hexanoate)

PDB for NP0183156 ((2z)-3,7-dimethylocta-2,6-dien-1-yl hexanoate)

3D PDB for NP0183156 ((2z)-3,7-dimethylocta-2,6-dien-1-yl hexanoate)

SMILES for NP0183156 ((2z)-3,7-dimethylocta-2,6-dien-1-yl hexanoate)

INCHI for NP0183156 ((2z)-3,7-dimethylocta-2,6-dien-1-yl hexanoate)

Structure for NP0183156 ((2z)-3,7-dimethylocta-2,6-dien-1-yl hexanoate)

3D Structure for NP0183156 ((2z)-3,7-dimethylocta-2,6-dien-1-yl hexanoate)