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Showing NP-Card for 1,4-cineol (NP0180547)

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Record Information
Version2.0
Created at2022-09-03 18:55:31 UTC
Updated at2022-09-03 18:55:31 UTC
NP-MRD IDNP0180547
Secondary Accession NumbersNone
Natural Product Identification
Common Name1,4-cineol
Description1,4-Cineole, also known as isocineole or p-cineole, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 1,4-Cineole is an extremely weak basic (essentially neutral) compound (based on its pKa). 1,4-Cineole is a camphor, cooling, and green tasting compound. Outside of the human body, 1,4-Cineole is found, on average, in the highest concentration within cardamoms and limes. 1,4-Cineole has also been detected, but not quantified in, several different foods, such as evergreen blackberries, herbs and spices, roselles, and star anises. This could make 1,4-cineole a potential biomarker for the consumption of these foods.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0180547 (1,4-cineol)


  Mrv1652310031711082D          

 11 12  0  0  0  0            999 V2000
    0.2757   -1.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047   -1.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    0.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2757    0.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    0.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2757    0.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9902    2.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9902   -1.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9902    1.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9902   -0.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7839    0.5445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  5  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
Download

3D MOL for NP0180547 (1,4-cineol)

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    2.6654   -0.7864   -0.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7454    0.1694    0.6787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1876    1.5548    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3653   -0.1010    0.2075 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1512    0.1120   -1.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3401    0.4866   -1.2817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7408    0.1706    0.1326 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0140    0.7840    0.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6288   -1.3079    0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1096   -1.5014    0.5356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6152    0.6675    0.8364 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6226   -1.7892    0.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2521   -0.8360   -1.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6572   -0.3397   -0.1170 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7871   -0.0167    1.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0561    1.8058    1.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3716    2.3021    0.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5582    1.6206   -0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2870   -0.8512   -1.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7757    0.8863   -1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3788    1.5873   -1.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8910   -0.0692   -2.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9588    1.2264    1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8372    0.0193    0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3154    1.6456   -0.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9460   -1.8682   -0.4910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1541   -1.5997    1.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2764   -2.1638   -0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1710   -1.8079    1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  2  1  1
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
  7 11  1  0
 10  4  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
M  END
Download

3D SDF for NP0180547 (1,4-cineol)


  Mrv1652310031711082D          

 11 12  0  0  0  0            999 V2000
    0.2757   -1.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047   -1.5180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    0.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2757    0.9570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7047    0.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2757    0.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9902    2.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9902   -1.1055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9902    1.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9902   -0.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7839    0.5445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  5  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0180547

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C12CCC(C)(CC1)O2

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-8(2)10-6-4-9(3,11-10)5-7-10/h8H,4-7H2,1-3H3

> <INCHI_KEY>
RFFOTVCVTJUTAD-UHFFFAOYSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.2493

> <EXACT_MASS>
154.135765198

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
18.89114577953177

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methyl-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
2.5043270663333335

> <ALOGPS_LOGS>
-3.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.20967657347654

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
45.7069

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4-cineol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0180547 (1,4-cineol)

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PDB for NP0180547 (1,4-cineol)
HEADER    PROTEIN                                 03-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-OCT-17         0                                  
HETATM    1  C   UNK     0       0.515  -2.834   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.182  -2.834   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.182   1.786   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.515   1.786   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.182   0.246   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.515   0.246   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.848   4.096   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.848  -2.064   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.848   2.556   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.848  -0.524   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.463   1.016   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    5    9                                                       
CONECT    4    6    9                                                       
CONECT    5    3   10                                                       
CONECT    6    4   10                                                       
CONECT    7    9                                                            
CONECT    8    1    2   10                                                  
CONECT    9    3    4    7   11                                             
CONECT   10    5    6    8   11                                             
CONECT   11    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0180547 (1,4-cineol)
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SMILES for NP0180547 (1,4-cineol)
CC(C)C12CCC(C)(CC1)O2
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INCHI for NP0180547 (1,4-cineol)
InChI=1S/C10H18O/c1-8(2)10-6-4-9(3,11-10)5-7-10/h8H,4-7H2,1-3H3
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View in JSmol
Synonyms
ValueSource
1,4-Epoxy-p-menthaneKegg
1,4-CineolHMDB
1-Isopropyl-4-methyl-7-oxabicyclo(2.2.1)heptaneHMDB
1-Isopropyl-4-methyl-7-oxabicyclo[2.2.1]heptaneHMDB
1-Isopropyl-4-methylbicyclo[2.2.1]heptaneHMDB
1-Methyl-4-(1-methylethyl)-7-oxabicyclo(2.2.1)heptaneHMDB
1-Methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptaneHMDB
1-Methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane, 9ciHMDB
7-Oxabicyclo(2.2.1)heptane, 1-isopropyl-4-methyl- (6ci)HMDB
IsocineoleHMDB
IsocinepleHMDB
p-CineoleHMDB
p-Menthane, 1,4-epoxyHMDB
Chemical FormulaC10H18O
Average Mass154.2493 Da
Monoisotopic Mass154.13577 Da
IUPAC Name1-methyl-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane
Traditional Name1,4-cineol
CAS Registry NumberNot Available
SMILES
CC(C)C12CCC(C)(CC1)O2
InChI Identifier
InChI=1S/C10H18O/c1-8(2)10-6-4-9(3,11-10)5-7-10/h8H,4-7H2,1-3H3
InChI KeyRFFOTVCVTJUTAD-UHFFFAOYSA-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentBicyclic monoterpenoids  
Alternative Parents
Substituents
  • P-menthane monoterpenoid
    • 

  • Bicyclic monoterpenoid
    • 

  • Tetrahydrofuran
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP2.31ALOGPS
logP2.5ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.71 m³·mol⁻¹ChemAxon
Polarizability18.89 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036096  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014936  
KNApSAcK IDC00010825  
Chemspider ID9702  
KEGG Compound IDC16909  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10106  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]