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Showing NP-Card for (-)-linalool (NP0278880)

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Record Information
Version2.0
Created at2022-09-09 04:04:15 UTC
Updated at2022-09-09 04:04:15 UTC
NP-MRD IDNP0278880
Secondary Accession NumbersNone
Natural Product Identification
Common Name(-)-linalool
DescriptionD-Linalool, also known as (3R)-linalool, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, D-linalool is considered to be an isoprenoid lipid molecule. (-)-linalool is found in Acca sellowiana, Acorus calamus, Actinidia arguta, Anthemis aciphylla, Azadirachta indica, Calycanthus floridus, Camellia sinensis, Capillipedium parviflorum, Chamaecyparis formosensis, Cistus incanus, Citrus aurantium, Citrus maxima, Citrus paradisi, Hesperis matronalis, Houttuynia cordata, Juniperus communis, Litsea cubeba, Lychnophora ericoides, Myrtus communis, Nicotiana mutabilis, Petasites japonicus, Rhodiola rosea, Saxifraga stolonifera, Siphonochilus aethiopicus, Skimmia laureola, Tarenna gracilipes, Thymus marschallianus and Vitis vinifera. (-)-linalool was first documented in 2008 (PMID: 18579302). D-Linalool is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0278880 ((-)-linalool)


  Mrv1652309272007282D          

 11 10  0  0  0  0            999 V2000
 9983.1225 9981.8339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9982.4091 9981.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.6941 9981.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.9796 9981.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.2628 9981.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.5482 9981.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.2628 9982.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.8379 9981.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.5533 9981.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.5348 9982.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.7102 9982.5478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  1 10  1  6  0  0  0
  1 11  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
Download

3D MOL for NP0278880 ((-)-linalool)

     RDKit          3D

 29 28  0  0  0  0  0  0  0  0999 V2000
    2.9251    0.3560    1.7432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4467   -0.4732    0.8323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1167   -0.0067   -0.5125 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3434   -1.0792   -1.5808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9992    1.0345   -0.8346 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7274    0.5223   -0.6718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3361   -0.5366   -0.5123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6526    0.1352   -0.6959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5929    0.1709    0.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4347   -0.4665    1.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8765    0.8681   -0.0633 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1855    0.0611    2.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0701    1.3946    1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2959   -1.5152    1.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3733   -1.0076   -1.9945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2440   -2.0713   -1.0563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5786   -1.0133   -2.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5795    1.8930   -0.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6534    0.9843   -1.6779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5545    1.3307    0.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2708   -1.3229   -1.2850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2258   -0.9614    0.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8025    0.6142   -1.6635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5219   -1.5772    1.3868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2551   -0.1686    2.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4362   -0.2487    1.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3013    1.3299    0.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7628    1.6368   -0.8622 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6241    0.1167   -0.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9 11  1  0
  9  8  2  3
  8  7  1  0
  7  6  1  0
  6  3  1  0
  3  4  1  0
  3  5  1  6
  3  2  1  0
  2  1  2  3
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
  8 23  1  0
  7 21  1  0
  7 22  1  0
  6 19  1  0
  6 20  1  0
  4 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  2 14  1  0
  1 12  1  0
  1 13  1  0
M  END
Download

3D SDF for NP0278880 ((-)-linalool)


  Mrv1652309272007282D          

 11 10  0  0  0  0            999 V2000
 9983.1225 9981.8339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9982.4091 9981.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9981.6941 9981.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.9796 9981.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.2628 9981.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.5482 9981.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.2628 9982.6592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.8379 9981.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.5533 9981.8339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.5348 9982.5478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.7102 9982.5478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  1 10  1  6  0  0  0
  1 11  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  9  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0278880

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC[C@@](C)(O)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3/t10-/m0/s1

> <INCHI_KEY>
CDOSHBSSFJOMGT-JTQLQIEISA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.253

> <EXACT_MASS>
154.1357652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
19.309217684081474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3,7-dimethylocta-1,6-dien-3-ol

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
2.647492452666667

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.459388377759243

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2856635235681075

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
50.2066

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-linalool

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0278880 ((-)-linalool)

Download
PDB for NP0278880 ((-)-linalool)
HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8635.1628632.757   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8633.8308631.988   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8632.4968632.757   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8631.1628631.988   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8629.8248632.757   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8628.4908631.988   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8629.8248634.297   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8636.4978631.988   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8637.8338632.757   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8635.9328634.089   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8634.3928634.089   0.000  0.00  0.00           O+0
CONECT    1    2    8   10   11                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    1    9                                                       
CONECT    9    8                                                            
CONECT   10    1                                                            
CONECT   11    1                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

Download
3D PDB for NP0278880 ((-)-linalool)
Download
SMILES for NP0278880 ((-)-linalool)
CC(C)=CCC[C@@](C)(O)C=C
Download
INCHI for NP0278880 ((-)-linalool)
InChI=1S/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3/t10-/m0/s1
Download
View in JSmol
Synonyms
ValueSource
(-)-3,7-Dimethyl-1,6-octadien-3-olChEBI
(-)-LinaloolChEBI
(3R)-3,7-Dimethyl-1,6-octadien-3-olChEBI
(3R)-LinaloolChEBI
(R)-(-)-LinaloolChEBI
(R)-3,7-Dimethyl-1,6-octadien-3-olChEBI
(-)-(3R)-LinaloolPhytoBank
(-)-LicareolPhytoBank
(-)-beta-LinaloolPhytoBank
(-)-β-LinaloolPhytoBank
(3R)-(-)-LinaloolPhytoBank
(R)-LinaloolPhytoBank
LicareolPhytoBank
l-LicareolPhytoBank
l-LinaloolPhytoBank
3,7-Dimethyl-1,6-octadien-3-olPhytoBank
(±)-LinaloolPhytoBank
2,6-Dimethyl-2,7-octadien-6-olPhytoBank
2-Methyl-1-prenyl-3-buten-2-olPhytoBank
3,7-Dimethyl-1,6-octadiene-3-olPhytoBank
3,7-Dimethyl-3-hydroxy-1,6-octadienePhytoBank
3,7-Dimethyl-3-ol-1,6-octadienePhytoBank
LinalolPhytoBank
LinaloolPhytoBank
Linalyl alcoholPhytoBank
PhantolPhytoBank
dl-LinaloolPhytoBank
beta-LinaloolPhytoBank
β-LinaloolPhytoBank
Chemical FormulaC10H18O
Average Mass154.2530 Da
Monoisotopic Mass154.13577 Da
IUPAC Name(3R)-3,7-dimethylocta-1,6-dien-3-ol
Traditional Name(-)-linalool
CAS Registry NumberNot Available
SMILES
CC(C)=CCC[C@@](C)(O)C=C
InChI Identifier
InChI=1S/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3/t10-/m0/s1
InChI KeyCDOSHBSSFJOMGT-JTQLQIEISA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acca sellowianaLOTUS Database
Acorus calamusLOTUS Database
Actinidia argutaLOTUS Database
Anthemis aciphyllaLOTUS Database
Azadirachta indicaLOTUS Database
Calycanthus floridusLOTUS Database
Camellia sinensisLOTUS Database
Capillipedium parviflorumLOTUS Database
Chamaecyparis formosensisLOTUS Database
Cistus incanusLOTUS Database
Citrus aurantiumLOTUS Database
Citrus maximaLOTUS Database
Citrus paradisiLOTUS Database
Hesperis matronalisLOTUS Database
Houttuynia cordataLOTUS Database
Juniperus communisLOTUS Database
Litsea cubebaLOTUS Database
Lychnophora ericoidesLOTUS Database
Myrtus communisLOTUS Database
Nicotiana mutabilisLOTUS Database
Petasites japonicusLOTUS Database
Rhodiola roseaLOTUS Database
Saxifraga stoloniferaLOTUS Database
Siphonochilus aethiopicusLOTUS Database
Skimmia laureolaLOTUS Database
Tarenna gracilipesLOTUS Database
Thymus marschallianusLOTUS Database
Vitis viniferaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentAcyclic monoterpenoids  
Alternative Parents
Substituents
  • Acyclic monoterpenoid
    • 

  • Tertiary alcohol
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.68ALOGPS
logP2.65ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)18.46ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.21 m³·mol⁻¹ChemAxon
Polarizability19.31 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014942  
KNApSAcK IDC00003047  
Chemspider IDNot Available
KEGG Compound IDC11388  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLinalool  
METLIN IDNot Available
PubChem Compound443158  
PDB IDNot Available
ChEBI ID28  
Good Scents IDNot Available
References
General References
  1. Batista PA, Werner MF, Oliveira EC, Burgos L, Pereira P, Brum LF, Santos AR: Evidence for the involvement of ionotropic glutamatergic receptors on the antinociceptive effect of (-)-linalool in mice. Neurosci Lett. 2008 Aug 8;440(3):299-303. doi: 10.1016/j.neulet.2008.05.092. Epub  2008 Jun 24. [PubMed:18579302  ] 
  2. LOTUS database [Link]