NP-MRD: Showing NP-Card for (Z)-3-Hexenyl hexanoate (NP0044914)

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Record Information

Version

2.0

Created at

2022-03-10 18:51:02 UTC

Updated at

2022-03-10 22:16:38 UTC

NP-MRD ID

NP0044914

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(Z)-3-Hexenyl hexanoate

Description

Cis-3-Hexenyl hexanoate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Cis-3-Hexenyl hexanoate is very hydrophobic, practically insoluble in water, and relatively neutral. Cis-3-Hexenyl hexanoate has a fruity, grassy, and green taste. Cis-3-Hexenyl hexanoate has been detected in citrus, fruits, herbs and spices, and tea. This could make cis-3-hexenyl hexanoate a potential biomarker for the consumption of these foods. Cis-3-Hexenyl hexanoate is the main volatile compound that gives passion fruit its distinctive aroma (https://Doi.Org/10.1590/S0101-20612011000200023). It is also found in cannabis plants (PMID:6991645 ) And in medical plants such as Chamomile (Matricaria recutita L. (Https://Doi: 10.1021/Bk-1993-0525.Ch020).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 35  0  0  0  0  0  0  0  0999 V2000
    4.3848    1.3833   -1.5144 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5267    0.4354   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6386   -0.7285   -0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6798   -1.0363    0.4125 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3955   -0.2513    1.5978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0481    0.3832    1.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0365   -0.4302    1.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5562   -1.0824    0.5366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0617   -0.9708   -0.5923 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7634   -1.9418    0.7989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9324   -0.9810    0.8149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0555   -0.2482   -0.5094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2481    0.7099   -0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4091    1.4660   -1.6868 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2541    1.2666   -2.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3998    2.4283   -1.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4314    1.1709   -2.0603 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5807    0.0027   -0.3751 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5098    0.9910    0.6061 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7697   -1.4085   -1.3257 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1099   -1.9715    0.2141 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1267    0.5624    1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5316   -0.9204    2.5400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9981    1.1271    2.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0185    1.1096    0.7654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9101   -2.6750   -0.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6792   -2.3951    1.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7937   -0.2669    1.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8444   -1.5609    1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3123   -0.9549   -1.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1366    0.2800   -0.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1718    0.1392   -0.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1152    1.4219    0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0615    2.5076   -1.5504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8290    0.9456   -2.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4870    1.4933   -1.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 13 32  1  0
 13 33  1  0
 12 30  1  0
 12 31  1  0
 11 28  1  0
 11 29  1  0
 10 26  1  0
 10 27  1  0
  6 24  1  0
  6 25  1  0
  5 22  1  0
  5 23  1  0
  4 21  1  0
  3 20  1  0
  2 18  1  0
  2 19  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
M  END

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      16.623   0.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.953   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.289   1.127   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.289   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.956   3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.622   2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.288   3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.621   4.977   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       9.955   2.667   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   14                                                       
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
cis-3-Hexenyl hexanoic acid	Generator
(3Z)-3-Hexenyl hexanoate	HMDB
(Z)-3-Hexen-1-ol, hexanoate	HMDB
(Z)-3-Hexenyl hexanoate	HMDB
(Z)-Hex-3-enyl hexanoate	HMDB
3-Hexen-1-ol hexanoate, cis	HMDB
3-Hexenyl ester(Z)-hexanoic acid	HMDB
cis-3-Hexenyl caproate	HMDB
cis-3-Hexenyl caproate (hexanoate)	HMDB
cis-3-Hexenyl hexoate	HMDB
cis-3-Hexenyl N-hexanoate	HMDB
cis-beta -Hexenyl caproate	HMDB
cis-Hexanoic acid, 3-hexenyl ester	HMDB
FEMA 3403	HMDB
Hexanoate(Z)-3-hexen-1-ol	HMDB
Hexanoic acid, (3Z)-3-hexen-1-yl ester	HMDB
Hexanoic acid, (3Z)-3-hexenyl ester	HMDB
Hexanoic acid, 3-hexenyl ester	HMDB
N-Caproic acid cis-3-hexenyl ester	HMDB
(Z)-3-Hexenyl hexanoic acid	Generator

Chemical Formula

C₁₂H₂₂O₂

Average Mass

198.3019 Da

Monoisotopic Mass

198.16198 Da

IUPAC Name

(3Z)-hex-3-en-1-yl hexanoate

Traditional Name

(3Z)-hex-3-en-1-yl hexanoate

CAS Registry Number

31501-11-8

SMILES

CCCCCC(=O)OCC\C=C/CC

InChI Identifier

InChI=1S/C12H22O2/c1-3-5-7-9-11-14-12(13)10-8-6-4-2/h5,7H,3-4,6,8-11H2,1-2H3/b7-5-

InChI Key

RGACQXBDYBCJCY-ALCCZGGFSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cannabis sativa	NULL	Not Available
Capsicum frutescens L.	Plant	KNApSAcK
Feijoa sellowiana	Plant	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

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 (LMFA07010594 )

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	4.41	ALOGPS
logP	3.81	ChemAxon
logS	-3.9	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	9	ChemAxon
Refractivity	60.03 m³·mol⁻¹	ChemAxon
Polarizability	24.38 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

HMDB0033378

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011408

KNApSAcK ID

Not Available

Chemspider ID

4509415

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5352543

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (Z)-3-Hexenyl hexanoate (NP0044914)

MOL for NP0044914 ((Z)-3-Hexenyl hexanoate)

3D MOL for NP0044914 ((Z)-3-Hexenyl hexanoate)

3D SDF for NP0044914 ((Z)-3-Hexenyl hexanoate)

3D-SDF for NP0044914 ((Z)-3-Hexenyl hexanoate)

PDB for NP0044914 ((Z)-3-Hexenyl hexanoate)

3D PDB for NP0044914 ((Z)-3-Hexenyl hexanoate)

SMILES for NP0044914 ((Z)-3-Hexenyl hexanoate)

INCHI for NP0044914 ((Z)-3-Hexenyl hexanoate)

Structure for NP0044914 ((Z)-3-Hexenyl hexanoate)

3D Structure for NP0044914 ((Z)-3-Hexenyl hexanoate)