NP-MRD: Showing NP-Card for Linalyl propionate (NP0045913)

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Record Information

Version

2.0

Created at

2022-03-17 19:45:18 UTC

Updated at

2022-03-17 19:45:18 UTC

NP-MRD ID

NP0045913

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Linalyl propionate

Description

Linalyl propionate, also known as fema 2645, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Linalyl propionate is an extremely weak basic (essentially neutral) compound (based on its pKa). Linalyl propionate is a bergamot, fresh, and lily tasting compound. Outside of the human body, Linalyl propionate has been detected, but not quantified in, gingers and herbs and spices. Linalyl propionate is found in Annona muricata, Lavandula angustifolia, Tanacetum parthenium and Zanthoxylum schinifolium. This could make linalyl propionate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305132D          

 15 14  0  0  0  0            999 V2000
    2.4750    5.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    4.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750   -0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    3.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    3.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  2  2  0  0  0  0
  9  8  1  0  0  0  0
 10  8  1  0  0  0  0
 11  3  1  0  0  0  0
 11  4  1  0  0  0  0
 11  9  2  0  0  0  0
 12  6  1  0  0  0  0
 13  5  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14 12  2  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045913

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H22O2/c1-6-12(14)15-13(5,7-2)10-8-9-11(3)4/h7,9H,2,6,8,10H2,1,3-5H3

> <INCHI_KEY>
WAQIIHCCEMGYKP-UHFFFAOYSA-N

> <FORMULA>
C13H22O2

> <MOLECULAR_WEIGHT>
210.3126

> <EXACT_MASS>
210.161979948

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
25.264175544886957

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7-dimethylocta-1,6-dien-3-yl propanoate

> <ALOGPS_LOGP>
4.52

> <JCHEM_LOGP>
3.789153709999998

> <ALOGPS_LOGS>
-3.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.057383590909502

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
63.98500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
linalool propionate

> <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       4.620   9.542   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.953   4.207   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.390  -2.461   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.080  -1.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.954   4.977   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.850   8.208   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.620   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.390   0.206   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.390   2.874   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.620  -1.127   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.620   6.875   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.620   4.207   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.160   6.875   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.850   5.541   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3   11                                                            
CONECT    4   11                                                            
CONECT    5   13                                                            
CONECT    6    1   12                                                       
CONECT    7    2   13                                                       
CONECT    8    9   10                                                       
CONECT    9    8   11                                                       
CONECT   10    8   13                                                       
CONECT   11    3    4    9                                                  
CONECT   12    6   14   15                                                  
CONECT   13    5    7   10   15                                             
CONECT   14   12                                                            
CONECT   15   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
Linalyl propionic acid	Generator
(1)-1,5-Dimethyl-1-vinylhex-4-enyl propionate	HMDB
1,5-Dimethyl-1-vinyl-4-hexenyl propionate	HMDB
1,6-Octadien-3-ol, 3,7-dimethyl-, 3-propanoate	HMDB
1,6-Octadien-3-ol, 3,7-dimethyl-, propanoate	HMDB
1,6-Octadien-3-ol, 3,7-dimethyl-, propionate	HMDB
1,6-Octadien-3-ol, 3,7-dimethyl-, propionate (7ci,8ci)	HMDB
3,7-Dimethyl-1,6-octadien-3-ol propanoate	HMDB
3,7-Dimethyl-1,6-octadien-3-yl propanoate	HMDB
3,7-Dimethyl-1,6-octadien-3-yl propionate	HMDB
FEMA 2645	HMDB
Linalool propionate	HMDB
Linalyl N-propionate	HMDB
Linalyl propanoate	HMDB
Propionic acid, linalyl ester	HMDB
Propionic acid, linalyl ester (6ci)	HMDB
3,7-Dimethylocta-1,6-dien-3-yl propanoic acid	Generator
Linalyl propionate	MeSH

Chemical Formula

C₁₃H₂₂O₂

Average Mass

210.3126 Da

Monoisotopic Mass

210.16198 Da

IUPAC Name

3,7-dimethylocta-1,6-dien-3-yl propanoate

Traditional Name

linalool propionate

CAS Registry Number

144-39-8

SMILES

CCC(=O)OC(C)(CCC=C(C)C)C=C

InChI Identifier

InChI=1S/C13H22O2/c1-6-12(14)15-13(5,7-2)10-8-9-11(3)4/h7,9H,2,6,8,10H2,1,3-5H3

InChI Key

WAQIIHCCEMGYKP-UHFFFAOYSA-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
Annona muricata	LOTUS Database	35616633
Lavandula angustifolia	LOTUS Database	35616633
Tanacetum parthenium	LOTUS Database	35616633
Zanthoxylum schinifolium	LOTUS Database	35616633
Zingiber officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Acyclic monoterpenoids

Alternative Parents

Substituents

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	4.52	ALOGPS
logP	3.79	ChemAxon
logS	-3.8	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	63.98 m³·mol⁻¹	ChemAxon
Polarizability	25.26 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

HMDB0030425

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002289

KNApSAcK ID

Not Available

Chemspider ID

55049

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61098

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Linalyl propionate (NP0045913)

MOL for NP0045913 (Linalyl propionate)

3D MOL for NP0045913 (Linalyl propionate)

3D SDF for NP0045913 (Linalyl propionate)

3D-SDF for NP0045913 (Linalyl propionate)

PDB for NP0045913 (Linalyl propionate)

3D PDB for NP0045913 (Linalyl propionate)

SMILES for NP0045913 (Linalyl propionate)

INCHI for NP0045913 (Linalyl propionate)

Structure for NP0045913 (Linalyl propionate)

3D Structure for NP0045913 (Linalyl propionate)