NP-MRD: Showing NP-Card for L-Linalool 3-glucoside (NP0045911)

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Record Information

Version

2.0

Created at

2022-03-17 19:45:16 UTC

Updated at

2022-03-17 19:45:16 UTC

NP-MRD ID

NP0045911

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-Linalool 3-glucoside

Description

D-Linalool 3-glucoside belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. D-Linalool 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, D-Linalool 3-glucoside has been detected, but not quantified in, several different foods, such as alcoholic beverages, common grapes, fruits, and tea. L-Linalool 3-glucoside is found in Arachniodes maximowiczii, Hypericum sikokumontanum, Jasminum sambac, Perilla frutescens and Pluchea indica. This could make D-linalool 3-glucoside a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241211392D          

 22 22  0  0  0  0            999 V2000
   -2.4212    0.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7171    1.1127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9749    0.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2707    1.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6624    1.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4715    1.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5506    2.3639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1649   -0.5302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4212   -0.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7566   -0.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1208    0.4086    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1826   -0.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8684    0.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8684    1.1423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1826   -0.8398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8684   -1.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8684   -1.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5555   -2.3639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1649   -1.2202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4777   -0.8398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5555   -0.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1649    0.3788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  4 11  1  0  0  0  0
  6  7  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
 13 21  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 20  1  0  0  0  0
 17 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045911

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC(C)(OC1OC(CO)C(O)C(O)C1O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C16H28O6/c1-5-16(4,8-6-7-10(2)3)22-15-14(20)13(19)12(18)11(9-17)21-15/h5,7,11-15,17-20H,1,6,8-9H2,2-4H3

> <INCHI_KEY>
FLXYFXDZJHWWGW-UHFFFAOYSA-N

> <FORMULA>
C16H28O6

> <MOLECULAR_WEIGHT>
316.3899

> <EXACT_MASS>
316.188588628

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
34.46760321429901

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3,7-dimethylocta-1,6-dien-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.44

> <JCHEM_LOGP>
0.8766568070000003

> <ALOGPS_LOGS>
-1.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.199733369574162

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.209645451144008

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083852137968

> <JCHEM_POLAR_SURFACE_AREA>
99.38000000000001

> <JCHEM_REFRACTIVITY>
82.61989999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.41e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3,7-dimethylocta-1,6-dien-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

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      -4.520   1.346   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.205   2.077   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.820   1.346   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.505   2.148   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.236   3.536   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.880   2.879   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.028   4.413   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.908  -0.990   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.520  -0.259   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.279  -1.064   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.225   0.763   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.208  -0.148   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.488   0.707   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.488   2.132   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.208  -1.568   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.488  -2.278   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.488  -3.703   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.770  -4.413   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.908  -2.278   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.625  -1.568   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.770  -0.148   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       5.908   0.707   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6   11                                             
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6                                                            
CONECT    8    9                                                            
CONECT    9    1    8   10                                                  
CONECT   10    9                                                            
CONECT   11    4   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14   21                                                  
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   20                                                            
CONECT   20   16   19   21                                                  
CONECT   21   13   20   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₂₈O₆

Average Mass

316.3899 Da

Monoisotopic Mass

316.18859 Da

IUPAC Name

2-[(3,7-dimethylocta-1,6-dien-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-[(3,7-dimethylocta-1,6-dien-3-yl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

99096-59-0

SMILES

CC(C)=CCCC(C)(OC1OC(CO)C(O)C(O)C1O)C=C

InChI Identifier

InChI=1S/C16H28O6/c1-5-16(4,8-6-7-10(2)3)22-15-14(20)13(19)12(18)11(9-17)21-15/h5,7,11-15,17-20H,1,6,8-9H2,2-4H3

InChI Key

FLXYFXDZJHWWGW-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
Arachniodes maximowiczii	Plant	KNApSAcK
Hypericum sikokumontanum	LOTUS Database	35616633
Jasminum sambac	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Pluchea indica	LOTUS Database	35616633
Vitis vinifera L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty acyl glycosides of mono- and disaccharides

Alternative Parents

Substituents

Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monoterpenoid
Monocyclic monoterpenoid
Oxane
Monosaccharide
Secondary alcohol
Polyol
Oxacycle
Acetal
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	0.44	ALOGPS
logP	0.88	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	82.62 m³·mol⁻¹	ChemAxon
Polarizability	34.47 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0030418

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002282

KNApSAcK ID

Not Available

Chemspider ID

13703042

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14190656

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for L-Linalool 3-glucoside (NP0045911)

MOL for NP0045911 (L-Linalool 3-glucoside)

3D MOL for NP0045911 (L-Linalool 3-glucoside)

3D SDF for NP0045911 (L-Linalool 3-glucoside)

3D-SDF for NP0045911 (L-Linalool 3-glucoside)

PDB for NP0045911 (L-Linalool 3-glucoside)

3D PDB for NP0045911 (L-Linalool 3-glucoside)

SMILES for NP0045911 (L-Linalool 3-glucoside)

INCHI for NP0045911 (L-Linalool 3-glucoside)

Structure for NP0045911 (L-Linalool 3-glucoside)

3D Structure for NP0045911 (L-Linalool 3-glucoside)