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Showing NP-Card for Dehydro-1,8-cineole (NP0048447)

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Record Information
Version2.0
Created at2022-03-17 20:56:37 UTC
Updated at2022-03-17 20:56:37 UTC
NP-MRD IDNP0048447
Secondary Accession NumbersNone
Natural Product Identification
Common NameDehydro-1,8-cineole
DescriptionDehydro-1,8-cineole, also known as 1,8-dehydrocineole or 1,8-cineole dehydro, belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds. Dehydro-1,8-cineole is an extremely weak basic (essentially neutral) compound (based on its pKa). Dehydro-1,8-cineole is a lemon and mint tasting compound. Outside of the human body, Dehydro-1,8-cineole has been detected, but not quantified in, a few different foods, such as herbs and spices, sweet bay, and tea. Dehydro-1,8-cineole is found in Artemisia annua , Caloglyphus rodriguezi, Dittrichia graveolens and Tanacetum macrophyllum. This could make dehydro-1,8-cineole a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048447 (Dehydro-1,8-cineole)


  Mrv0541 05061308532D          

 11 12  0  0  0  0            999 V2000
    1.8383   -0.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4864   -1.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0532   -2.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -1.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9605   -0.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2262   -2.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2052   -0.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9228   -1.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6614   -1.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0655   -1.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8140   -2.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  2  0  0  0  0
  7  5  1  0  0  0  0
  8  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  8  1  0  0  0  0
 10  3  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
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3D MOL for NP0048447 (Dehydro-1,8-cineole)

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3D SDF for NP0048447 (Dehydro-1,8-cineole)

  Mrv0541 05061308532D          

 11 12  0  0  0  0            999 V2000
    1.8383   -0.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4864   -1.3502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0532   -2.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -1.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9605   -0.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2262   -2.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2052   -0.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9228   -1.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6614   -1.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0655   -1.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8140   -2.1055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  2  0  0  0  0
  7  5  1  0  0  0  0
  8  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  8  1  0  0  0  0
 10  3  1  0  0  0  0
 10  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048447

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2(C)CCC1C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h4,6,8H,5,7H2,1-3H3

> <INCHI_KEY>
LOOYOTLEOHYYOV-UHFFFAOYSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.2334

> <EXACT_MASS>
152.120115134

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
17.84680350370494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3,3-trimethyl-2-oxabicyclo[2.2.2]oct-5-ene

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.142405409666667

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.235564070992928

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
46.8235

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,3-trimethyl-2-oxabicyclo[2.2.2]oct-5-ene

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048447 (Dehydro-1,8-cineole)
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PDB for NP0048447 (Dehydro-1,8-cineole)
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       3.431  -1.002   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.641  -2.520   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.966  -4.823   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.222  -2.543   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.793  -0.213   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.422  -3.953   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.250  -1.344   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.723  -1.886   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.101  -2.506   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.989  -3.283   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.386  -3.930   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    6    8                                                       
CONECT    5    7    8                                                       
CONECT    6    4   10                                                       
CONECT    7    5   10                                                       
CONECT    8    4    5    9                                                  
CONECT    9    1    2    8   11                                             
CONECT   10    3    6    7   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 NP0048447 (Dehydro-1,8-cineole)
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SMILES for NP0048447 (Dehydro-1,8-cineole)
CC1(C)OC2(C)CCC1C=C2
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INCHI for NP0048447 (Dehydro-1,8-cineole)
InChI=1S/C10H16O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h4,6,8H,5,7H2,1-3H3
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Synonyms
ValueSource
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]oct-5-eneHMDB
1,8-Cineole dehydroHMDB
1,8-DehydrocineoleHMDB
1,8-Epoxy-p-menth-2-eneHMDB
2,3-Dehydro-1,8-cineolHMDB
2,3-Dehydro-1,8-cineoleHMDB
Dehydro-1,8-cineolHMDB
Dehydro-1,8-cyneoleHMDB
Dehydro-1.8-cineoleHMDB
DehydrocineoleHMDB
Chemical FormulaC10H16O
Average Mass152.2334 Da
Monoisotopic Mass152.12012 Da
IUPAC Name1,3,3-trimethyl-2-oxabicyclo[2.2.2]oct-5-ene
Traditional Name1,3,3-trimethyl-2-oxabicyclo[2.2.2]oct-5-ene
CAS Registry Number92760-25-3
SMILES
CC1(C)OC2(C)CCC1C=C2
InChI Identifier
InChI=1S/C10H16O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h4,6,8H,5,7H2,1-3H3
InChI KeyLOOYOTLEOHYYOV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Artemisia annuaPlant
Caloglyphus rodrigueziAnimalia
Dittrichia graveolensPlant
Laurus nobilis L.FooDB
Tanacetum macrophyllumPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and  two ring double bonds.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrans  
Sub ClassNot Available
Direct ParentPyrans  
Alternative Parents
Substituents
  • Pyran
    • 

  • Oxane
    • 

  • Oxacycle
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organic oxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP2.78ALOGPS
logP2.14ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.82 m³·mol⁻¹ChemAxon
Polarizability17.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036085  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014921  
KNApSAcK IDC00010827  
Chemspider ID456244  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound523035  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available