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Showing NP-Card for (R)-Lavandulol (NP0048428)

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Record Information
Version2.0
Created at2022-03-17 20:56:19 UTC
Updated at2022-03-17 20:56:19 UTC
NP-MRD IDNP0048428
Secondary Accession NumbersNone
Natural Product Identification
Common Name(R)-Lavandulol
Description(R)-Lavandulol belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle (R)-Lavandulol is an extremely weak basic (essentially neutral) compound (based on its pKa) (R)-Lavandulol is a herbal tasting compound. Outside of the human body, (R)-Lavandulol is found, on average, in the highest concentration within rosemaries and peppermints. This could make (R)-lavandulol a potential biomarker for the consumption of these foods. (R)-Lavandulol is found in Achillea millefolium, Ajania gracilis, Antiphiona pinnatisecta, Artemisia arborescens, Artemisia tridentata, Artemisia tridentata spp.spiciformis, Aster scaber, Bellis perennis, Cistus creticus, Cistus incanus, Curcuma amanda Roxb, Diplotaenia cachrydifolia, Elsholtzia fruticosa, Glycyrrhiza glabra, Lavandin abrialis, Lavandula angustifolia, Lavandula bipinnata , Lavandula stoechas , Ligusticum sinense , Lippia chevalieri, Necrodes surinamensis, Ocimum basilicum , Peucedanum paniculatum L., Salvia sclarea, Santolina corsica Jordan et Fourr and Tessaria fastigiata. (R)-Lavandulol was first documented in 2001 (PMID: 11504023). A monoterpenoid alcohol that is hepta-1-5-diene which is substituted at positions 2 and 6 by methyl groups and at position 3 by a hydroxymethyl group (PMID: 11809456) (PMID: 17193200).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048428 ((R)-Lavandulol)


  Mrv0541 05061308512D          

 11 10  0  0  0  0            999 V2000
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  5  2  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
M  END
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3D MOL for NP0048428 ((R)-Lavandulol)

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3D SDF for NP0048428 ((R)-Lavandulol)

  Mrv0541 05061308512D          

 11 10  0  0  0  0            999 V2000
    1.5395   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  5  2  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048428

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC(CO)C(C)=C

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

> <INCHI_KEY>
CZVXBFUKBZRMKR-UHFFFAOYSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.2493

> <EXACT_MASS>
154.135765198

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
19.233482484296843

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
2.3248136676666666

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.006096902463728

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4839332148623647

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
50.1342

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lavandulol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048428 ((R)-Lavandulol)
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PDB for NP0048428 ((R)-Lavandulol)
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       2.874  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.207   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.207  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.207   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.874  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.874   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.206   0.770   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4    9                                                            
CONECT    5    6    8                                                       
CONECT    6    5   10                                                       
CONECT    7   10   11                                                       
CONECT    8    1    2    5                                                  
CONECT    9    3    4   10                                                  
CONECT   10    6    7    9                                                  
CONECT   11    7                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0048428 ((R)-Lavandulol)
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SMILES for NP0048428 ((R)-Lavandulol)
CC(C)=CCC(CO)C(C)=C
Download
INCHI for NP0048428 ((R)-Lavandulol)
InChI=1S/C10H18O/c1-8(2)5-6-10(7-11)9(3)4/h5,10-11H,3,6-7H2,1-2,4H3
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View in JSmol
Synonyms
ValueSource
5-Methyl-2-(1-methylethenyl)hex-4-en-1-olChEBI
(-)-2-Isopropenyl-5-methyl-4-hexen-1-olHMDB
(-)-LavandulolHMDB
(2R)-5-Methyl-2-(1-methylethenyl)hex-4-en-1-olHMDB
(2R)-5-Methyl-2-(prop-1-en-2-yl)hex-4-en-1-olHMDB
(R)-(-)-LavandulolHMDB
(R)-5-Methyl-2-(1-methylethenyl)-4-hexen-1-olHMDB
2-Isopropenyl-5-methyl-(-)-4-hexen-1-olHMDB
4-Hexen-1-ol, 2-isopropenyl-5-methyl-, (-)- (8ci)HMDB
5-Methyl-2-(1-methylethenyl)-(R)-4-hexen-1-olHMDB
2-Isopropenyl-5-methyl-4-hexen-1-olMeSH
LavandulolMeSH
5-Methyl-2-(1-methylethenyl)-4-hexen-1-olMeSH
Chemical FormulaC10H18O
Average Mass154.2493 Da
Monoisotopic Mass154.13577 Da
IUPAC Name5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-ol
Traditional Namelavandulol
CAS Registry Number498-16-8
SMILES
CC(C)=CCC(CO)C(C)=C
InChI Identifier
InChI=1S/C10H18O/c1-8(2)5-6-10(7-11)9(3)4/h5,10-11H,3,6-7H2,1-2,4H3
InChI KeyCZVXBFUKBZRMKR-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea millefoliumLOTUS Database
Ajania gracilisLOTUS Database
Antiphiona pinnatisectaLOTUS Database
Artemisia arborescensLOTUS Database
Artemisia tridentataLOTUS Database
Artemisia tridentata spp.spiciformisPlant
Aster scaberLOTUS Database
Bellis perennisLOTUS Database
Cistus creticusPlant
Cistus incanusLOTUS Database
Curcuma amanda RoxbPlant
Diplotaenia cachrydifoliaLOTUS Database
Elsholtzia fruticosaLOTUS Database
Glycyrrhiza glabraLOTUS Database
Lavandin abrialis-
Lavandula angustifoliaLOTUS Database
Lavandula bipinnataPlant
Lavandula stoechasPlant
Ligusticum sinensePlant
Lippia chevalieriPlant
Mentha x piperitaFooDB
Necrodes surinamensisLOTUS Database
Ocimum basilicumPlant
Peucedanum paniculatum L.Plant
Salvia rosmarinusFooDB
Salvia sclareaLOTUS Database
Santolina corsica Jordan et FourrPlant
Tessaria fastigiataLOTUS 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
    • 

  • Fatty alcohol
    • 

  • Fatty acyl
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • 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
logP2.81ALOGPS
logP2.32ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)18.01ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.13 m³·mol⁻¹ChemAxon
Polarizability19.23 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036041  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014861  
KNApSAcK IDC00034575  
Chemspider ID84888  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLavandulol  
METLIN IDNot Available
PubChem Compound94060  
PDB IDNot Available
ChEBI ID50281  
Good Scents IDNot Available
References
General References
  1. Innocenzi PJ, Hall DR, Cross JV: Components of male aggregation pheromone of strawberry blossom weevil, Anthonomus rubi herbst. (Coleoptera:Curculionidae). J Chem Ecol. 2001 Jun;27(6):1203-18. doi: 10.1023/a:1010320130073. [PubMed:11504023  ] 
  2. Gunawardena K, Rivera SB, Epstein WW: The monoterpenes of Artemisia tridentata ssp. vaseyana, Artemisia cana ssp. viscidula and Artemisia tridentata ssp. spiciformis. Phytochemistry. 2002 Jan;59(2):197-203. doi: 10.1016/s0031-9422(01)00438-1. [PubMed:11809456  ] 
  3. Sakauchi H, Kiyota H, Takigawa SY, Oritani T, Kuwahara S: Enzymatic resolution and odor description of both enantiomers of lavandulol, a fragrance of lavender oil. Chem Biodivers. 2005 Sep;2(9):1183-6. doi: 10.1002/cbdv.200590088. [PubMed:17193200  ]