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Showing NP-Card for Myrcenol (NP0048452)

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Record Information
Version2.0
Created at2022-03-17 20:56:41 UTC
Updated at2022-03-17 20:56:42 UTC
NP-MRD IDNP0048452
Secondary Accession NumbersNone
Natural Product Identification
Common NameMyrcenol
DescriptionMyrcenol belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). Myrcenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Myrcenol is a citrus, floral, and fresh tasting compound. Outside of the human body, Myrcenol has been detected, but not quantified in, sweet basils. This could make myrcenol a potential biomarker for the consumption of these foods. Myrcenol is found in Basella alba, Chamaecyparis pisifera, Cotinus coggygria, Curcuma mangga , Elsholtzia pilosa, Acca sellowiana, Glycyrrhiza glabra, Hamamelis virginiana, Ocimum gratissimum, Thymus vulgaris and Vitis vinifera. Myrcenol was first documented in 1986 (PMID: 24305835). A monoterpenoid that is oct-7-en-2-ol substituted by a methyl group at position 2 and a methylidene group at position 6 respectively (PMID: 18640191).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048452 (Myrcenol)


  Mrv0541 05061308532D          

 11 10  0  0  0  0            999 V2000
    2.9684    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    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
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    3.3000    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    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
    2.2539    2.4750    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
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
  9  2  2  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
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3D MOL for NP0048452 (Myrcenol)

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3D SDF for NP0048452 (Myrcenol)

  Mrv0541 05061308532D          

 11 10  0  0  0  0            999 V2000
    2.9684    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    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
    1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    3.3000    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    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
    2.2539    2.4750    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
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
  9  2  2  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048452

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(O)CCCC(=C)C=C

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

> <INCHI_KEY>
DUNCVNHORHNONW-UHFFFAOYSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.2493

> <EXACT_MASS>
154.135765198

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
19.042571810279313

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyl-6-methylideneoct-7-en-2-ol

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
2.4715649330000007

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.607806887655226

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2207452673396038

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
49.3651

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.65e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
myrcenol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048452 (Myrcenol)
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PDB for NP0048452 (Myrcenol)
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       5.541   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.541   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.080   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.207   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.874   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.874   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.540   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.207   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   10                                                            
CONECT    5    1    9                                                       
CONECT    6    7    8                                                       
CONECT    7    6    9                                                       
CONECT    8    6   10                                                       
CONECT    9    2    5    7                                                  
CONECT   10    3    4    8   11                                             
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0048452 (Myrcenol)
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SMILES for NP0048452 (Myrcenol)
CC(C)(O)CCCC(=C)C=C
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INCHI for NP0048452 (Myrcenol)
InChI=1S/C10H18O/c1-5-9(2)7-6-8-10(3,4)11/h5,11H,1-2,6-8H2,3-4H3
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View in JSmol
Synonyms
ValueSource
2-Methyl-6-methylene-7-octen-2-olHMDB
2-Methyl-6-methylene-7-octen-4-olHMDB
2-Methyl-6-methyleneoct-7-en-2-olHMDB
3-Methylene-7-methyl-1-octen-7-olHMDB
7-Hydroxy-7-methyl-3-methylene-1-octeneHMDB
7-Methyl-3-methylene-1-octen-7-olHMDB
Chemical FormulaC10H18O
Average Mass154.2493 Da
Monoisotopic Mass154.13577 Da
IUPAC Name2-methyl-6-methylideneoct-7-en-2-ol
Traditional Namemyrcenol
CAS Registry Number543-39-5
SMILES
CC(C)(O)CCCC(=C)C=C
InChI Identifier
InChI=1S/C10H18O/c1-5-9(2)7-6-8-10(3,4)11/h5,11H,1-2,6-8H2,3-4H3
InChI KeyDUNCVNHORHNONW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Basella albaLOTUS Database
Chamaecyparis pisiferaLOTUS Database
Cotinus coggygriaLOTUS Database
Curcuma manggaPlant
Elsholtzia pilosaLOTUS Database
Feijoa sellowianaPlant
Glycyrrhiza glabraLOTUS Database
Hamamelis virginianaLOTUS Database
Ocimum basilicumFooDB
Ocimum gratissimumLOTUS Database
Thymus vulgarisLOTUS Database
VitisFooDB
Vitis viniferaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassAlcohols and polyols  
Direct ParentTertiary alcohols  
Alternative Parents
Substituents
  • Tertiary alcohol
    • 

  • Hydrocarbon derivative
    • 

  • 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
logP3.03ALOGPS
logP2.47ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)18.61ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity49.37 m³·mol⁻¹ChemAxon
Polarizability19.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036107  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014951  
KNApSAcK IDNot Available
Chemspider ID10510  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMyrcenol  
METLIN IDNot Available
PubChem Compound10975  
PDB IDNot Available
ChEBI ID87529  
Good Scents IDNot Available
References
General References
  1. Lapczynski A, Bhatia SP, Letizia CS, Api AM: Fragrance material review on myrcenol. Food Chem Toxicol. 2008 Nov;46 Suppl 11:S234-6. doi: 10.1016/j.fct.2008.06.061. Epub 2008 Jul 2. [PubMed:18640191  ] 
  2. Hunt DW, Borden JH, Pierce HD Jr, Slessor KN, King GG, Czyzewska EK: Sex-specific production of ipsdienol and myrcenol byDendroctonus ponderosae (Coleoptera: Scolytidae) exposed to myrcene vapors. J Chem Ecol. 1986 Jul;12(7):1579-86. doi: 10.1007/BF01020265. [PubMed:24305835  ]