NP-MRD: Showing NP-Card for Linalyl formate (NP0085918)

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Record Information

Version

2.0

Created at

2022-04-29 06:20:40 UTC

Updated at

2022-04-29 06:20:40 UTC

NP-MRD ID

NP0085918

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Linalyl formate

Description

Linalyl formate, also known as fema 2642, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Linalyl formate is an extremely weak basic (essentially neutral) compound (based on its pKa). Linalyl formate is a bergamot, bitter, and citrus tasting compound. Outside of the human body, Linalyl formate has been detected, but not quantified in, fruits. Linalyl formate is found in Piper nigrum , Plectranthus glabratus, Prunus spp. , Salvia sclarea, Zanthoxylum schinifolium, Zanthoxylum simulans and Zingiber zerumbet. This could make linalyl formate a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 30  0  0  0  0  0  0  0  0999 V2000
   -2.1979   -2.3196    0.8728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6730   -1.5371   -0.0509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9207   -0.0626   -0.1321 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9714    0.1597   -1.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6001    0.5609   -0.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4259    0.3130    0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7254    0.9114    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8423    0.2330    0.1676 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1247    0.8783   -0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8264   -1.2409    0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3732    0.4615    1.0765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6158    1.8120    1.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4586    2.6431    0.2753 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8558   -1.9517    1.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9754   -3.3755    0.8705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0260   -1.9683   -0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5412    0.3510   -2.1914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6215    1.0205   -0.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6333   -0.7317   -1.1866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6644    1.6204   -0.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1709    0.0117   -1.3849 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0507    0.7074    1.5929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5813   -0.7747    0.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7502    2.0008    0.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5677    0.3403   -1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8168    0.6792    0.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0554    1.9605   -0.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8309   -1.6888    0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4880   -1.4679    1.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1827   -1.7312   -0.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9690    2.1853    2.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
  8  7  2  3
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  0
  3 11  1  1
 11 12  1  0
 12 13  2  0
  3  2  1  0
  2  1  2  3
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
  7 24  1  0
  6 22  1  0
  6 23  1  0
  5 20  1  0
  5 21  1  0
  4 17  1  0
  4 18  1  0
  4 19  1  0
 12 31  1  0
  2 16  1  0
  1 14  1  0
  1 15  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       1.953   4.207   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.390  -2.461   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.080  -1.127   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.954   4.977   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.620   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.390   0.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.390   2.874   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.620   6.875   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.620  -1.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.620   4.207   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.850   8.208   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.850   5.541   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   10                                                            
CONECT    3   10                                                            
CONECT    4   11                                                            
CONECT    5    1   11                                                       
CONECT    6    7    8                                                       
CONECT    7    6   10                                                       
CONECT    8    6   11                                                       
CONECT    9   12   13                                                       
CONECT   10    2    3    7                                                  
CONECT   11    4    5    8   13                                             
CONECT   12    9                                                            
CONECT   13    9   11                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

Synonyms

Value	Source
Linalyl formic acid	Generator
1,6-Octadien-3-ol, 3,7-dimethyl-, 3-formate	HMDB
1,6-Octadien-3-ol, 3,7-dimethyl-, formate	HMDB
3,7-Dimethyl-1,6-octadien-3-ol formate	HMDB
3,7-Dimethyl-1,6-octadien-3-yl formate	HMDB
FEMA 2642	HMDB
Linalool formate	HMDB
3,7-Dimethylocta-1,6-dien-3-yl formic acid	Generator
Linalyl formate	MeSH

Chemical Formula

C₁₁H₁₈O₂

Average Mass

182.2594 Da

Monoisotopic Mass

182.13068 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC(C)(OC=O)C=C

InChI Identifier

InChI=1S/C11H18O2/c1-5-11(4,13-9-12)8-6-7-10(2)3/h5,7,9H,1,6,8H2,2-4H3

InChI Key

JZOCDHMHLGUPFI-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
Piper nigrum L.	Plant	KNApSAcK
Plectranthus glabratus	LOTUS Database	35616633
Prunus spp.	Plant	KNApSAcK
Salvia sclarea	LOTUS Database	35616633
Zanthoxylum schinifolium	LOTUS Database	35616633
Zanthoxylum simulans	LOTUS Database	35616633
Zingiber zerumbet	LOTUS Database	35616633

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	3.74	ALOGPS
logP	3.04	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-6.8	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	6	ChemAxon
Refractivity	54.87 m³·mol⁻¹	ChemAxon
Polarizability	21.04 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

HMDB0030424

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002288

KNApSAcK ID

Not Available

Chemspider ID

54999

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61040

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Linalyl formate (NP0085918)

MOL for NP0085918 (Linalyl formate)

3D MOL for NP0085918 (Linalyl formate)

3D SDF for NP0085918 (Linalyl formate)

3D-SDF for NP0085918 (Linalyl formate)

PDB for NP0085918 (Linalyl formate)

3D PDB for NP0085918 (Linalyl formate)

SMILES for NP0085918 (Linalyl formate)

INCHI for NP0085918 (Linalyl formate)

Structure for NP0085918 (Linalyl formate)

3D Structure for NP0085918 (Linalyl formate)