NP-MRD: Showing NP-Card for cis-3-hexenyl isovalerate (NP0266028)

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Record Information

Version

2.0

Created at

2022-09-08 10:14:00 UTC

Updated at

2022-09-08 10:14:01 UTC

NP-MRD ID

NP0266028

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cis-3-hexenyl isovalerate

Description

Cis-3-Hexenyl 3-methylbutanoate, also known as (Z)-3-hexenyl isopentanoate or (Z)-hex-3-enyl isovalerate, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Cis-3-Hexenyl 3-methylbutanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Cis-3-Hexenyl 3-methylbutanoate is a food flavour. Cis-3-Hexenyl 3-methylbutanoate is an apple, fresh, and fruity tasting compound. cis-3-hexenyl isovalerate is found in Artemisia annua, Matricaria matricarioides and Mentha canadensis. Outside of the human body,.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 32  0  0  0  0  0  0  0  0999 V2000
    5.3437    0.5561   -0.3678 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4566   -0.6415    0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3624   -0.6881   -0.9289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0945   -0.5818   -0.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6492   -0.4030    0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.8918    0.9733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2653    1.0115    0.2044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3750    0.1821    0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4017   -0.7761    1.0270 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4795    0.5241   -0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6398   -0.4266   -0.5738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6847    0.0458   -1.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2447   -0.2557    0.8196 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7191    1.4411   -0.5980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0817    0.7759    0.4379 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8685    0.2861   -1.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1204   -1.5271   -0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2191   -0.6030    1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6648   -0.8245   -1.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3399   -0.6329   -1.4384 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8578   -1.2061    0.9468 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3818   -0.5643    1.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5851    1.7040    0.6350 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6387    1.0760    2.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0694    0.5807   -1.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8498    1.5288   -0.3904 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3761   -1.4733   -0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1447    0.9951   -1.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4296   -0.7410   -1.7937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1500    0.2916   -2.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3467   -0.2169    0.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9194    0.7205    1.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8906   -1.0492    1.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  2 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
M  END

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      -6.105   1.746   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.898  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.771   0.976   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.771  -0.564   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.437  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.104  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.231  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.565  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.897  -1.334   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.897  -2.874   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.564  -0.564   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2   10                                                            
CONECT    3   10                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   13                                                       
CONECT    9   10   11                                                       
CONECT   10    2    3    9                                                  
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

Synonyms

Value	Source
cis-3-Hexenyl 3-methylbutanoic acid	Generator
(3Z)-3-Hexenyl 3-methylbutanoate	HMDB
(Z)-3-Hexen-1-yl isovalerate	HMDB
(Z)-3-Hexenyl 3-methylbutanoate	HMDB
(Z)-3-Hexenyl 3-methylbutyrate	HMDB
(Z)-3-Hexenyl isopentanoate	HMDB
(Z)-3-Hexenyl isovalerate	HMDB
(Z)-Hex-3-enyl 3-methylbutanoate	HMDB
(Z)-Hex-3-enyl isovalerate	HMDB
3-Hexen-1-yl 3-methylbutanoate	HMDB
3-Hexenyl 3-methylbutanoate	HMDB
3-Hexenyl ester(Z)-isovaleric acid	HMDB
3-Hexenyl isopentanoate	HMDB
3-Hexenyl isovalerate	HMDB
3-Methyl-3-hexenyl ester(Z)-butanoic acid	HMDB
Butanoic acid, 3-methyl-, (3Z)-3-hexen-1-yl ester	HMDB
Butanoic acid, 3-methyl-, (3Z)-3-hexenyl ester	HMDB
Butanoic acid, 3-methyl-, 3-hexen-1-yl ester	HMDB
Butanoic acid, 3-methyl-, 3-hexenyl ester	HMDB
cis-3-Hexenyl isopentanoate	HMDB
cis-3-Hexenyl isovalerate	HMDB
cis-Hex-3-enyl 3-methylbutanoate	HMDB
FEMA 3498	HMDB
Hex-3-enyl isovalerate	HMDB
Isovaleric acid cis-3-hexenyl ester	HMDB
Isovaleric acid, 3-hexenyl ester	HMDB
(Z)-3-Hexenyl 3-methylbutanoic acid	Generator

Chemical Formula

C₁₁H₂₀O₂

Average Mass

184.2753 Da

Monoisotopic Mass

184.14633 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC\C=C/CCOC(=O)CC(C)C

InChI Identifier

InChI=1S/C11H20O2/c1-4-5-6-7-8-13-11(12)9-10(2)3/h5-6,10H,4,7-9H2,1-3H3/b6-5-

InChI Key

AIQLNKITFBJPFO-WAYWQWQTSA-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
Artemisia annua	LOTUS Database	35616633
Matricaria matricarioides	LOTUS Database	35616633
Mentha sachalinensis	LOTUS Database	35616633

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 (LMFA07010592 )

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	3.65	ALOGPS
logP	3.21	ChemAxon
logS	-3.2	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	7	ChemAxon
Refractivity	55.38 m³·mol⁻¹	ChemAxon
Polarizability	22.22 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

HMDB0038278

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017576

KNApSAcK ID

C00029347

Chemspider ID

4519169

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5367681

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for cis-3-hexenyl isovalerate (NP0266028)

MOL for NP0266028 (cis-3-hexenyl isovalerate)

3D MOL for NP0266028 (cis-3-hexenyl isovalerate)

3D SDF for NP0266028 (cis-3-hexenyl isovalerate)

3D-SDF for NP0266028 (cis-3-hexenyl isovalerate)

PDB for NP0266028 (cis-3-hexenyl isovalerate)

3D PDB for NP0266028 (cis-3-hexenyl isovalerate)

SMILES for NP0266028 (cis-3-hexenyl isovalerate)

INCHI for NP0266028 (cis-3-hexenyl isovalerate)

Structure for NP0266028 (cis-3-hexenyl isovalerate)

3D Structure for NP0266028 (cis-3-hexenyl isovalerate)