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Showing NP-Card for 1,4-Dimethyl-7-ethylazulene (NP0048518)

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Record Information
Version2.0
Created at2022-03-17 20:57:43 UTC
Updated at2022-03-17 20:57:43 UTC
NP-MRD IDNP0048518
Secondary Accession NumbersNone
Natural Product Identification
Common Name1,4-Dimethyl-7-ethylazulene
Description1,4-Dimethyl-7-ethylazulene, also known as 7-ethyl-1,4-dimethyl-azulene or camazulene, belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. Thus, 1,4-dimethyl-7-ethylazulene is considered to be an isoprenoid lipid molecule. 1,4-Dimethyl-7-ethylazulene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 1,4-Dimethyl-7-ethylazulene has been detected, but not quantified in, a few different foods, such as anises, german camomiles, and roman camomiles. 1,4-Dimethyl-7-ethylazulene is found in Achillea, Achillea alpina, Achillea collina, Achillea millefolium , Achillea moschata, Achillea,Artemisia spp., Artemisia absinthium , Artemisia arborescens, Artemisia argyi, Artemisia jacutica, Artemisia macrocephala, Artemisia spp. , Artemisia thuscula, Chamaemalum nobile, Chamomilla rectita, Chamomilla recutina, Leonurus sibiricus, Lindera strychnifolia , Matricaria chamomilla , Nepeta leucophylla, Pinus eldarica, Pinus kochiana, Pinus pallasiana, Pinus sosnowskyi, Pinus sylvestris L.var.sylvestris. , Rhanterium epapposum, Skimmia laureola and Stevia serrata. This could make 1,4-dimethyl-7-ethylazulene a potential biomarker for the consumption of these foods.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0048518 (1,4-Dimethyl-7-ethylazulene)


  Mrv0541 05061309102D          

 14 15  0  0  0  0            999 V2000
    3.4036    3.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2027    0.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7017    3.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7050    3.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    1.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    1.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863    2.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863    0.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    2.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    2.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    2.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
 10  2  1  0  0  0  0
 10  5  1  0  0  0  0
 11  3  1  0  0  0  0
 11  6  1  0  0  0  0
 12  4  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13  8  1  0  0  0  0
 13 10  2  0  0  0  0
 14  9  1  0  0  0  0
 14 11  2  0  0  0  0
 14 13  1  0  0  0  0
M  END
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3D MOL for NP0048518 (1,4-Dimethyl-7-ethylazulene)

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3D SDF for NP0048518 (1,4-Dimethyl-7-ethylazulene)

  Mrv0541 05061309102D          

 14 15  0  0  0  0            999 V2000
    3.4036    3.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2027    0.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7017    3.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7050    3.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    1.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    1.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863    2.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863    0.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    2.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    2.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    2.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
 10  2  1  0  0  0  0
 10  5  1  0  0  0  0
 11  3  1  0  0  0  0
 11  6  1  0  0  0  0
 12  4  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13  8  1  0  0  0  0
 13 10  2  0  0  0  0
 14  9  1  0  0  0  0
 14 11  2  0  0  0  0
 14 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048518

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1=CC2=C(C)C=CC2=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H16/c1-4-12-7-5-10(2)13-8-6-11(3)14(13)9-12/h5-9H,4H2,1-3H3

> <INCHI_KEY>
GXGJIOMUZAGVEH-UHFFFAOYSA-N

> <FORMULA>
C14H16

> <MOLECULAR_WEIGHT>
184.2768

> <EXACT_MASS>
184.125200512

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
23.046836357362473

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-ethyl-1,4-dimethylazulene

> <ALOGPS_LOGP>
4.80

> <JCHEM_LOGP>
4.947555405666667

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
62.23280000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
chamazulene

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0048518 (1,4-Dimethyl-7-ethylazulene)
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PDB for NP0048518 (1,4-Dimethyl-7-ethylazulene)
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       6.353   7.387   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.112   0.130   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.310   6.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.916   5.954   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.956   1.975   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.881   3.362   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.624   3.362   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.786   2.116   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.454   5.092   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.454   1.632   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.786   4.608   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.956   4.750   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.250   2.592   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.250   4.132   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4    1   12                                                       
CONECT    5    7   10                                                       
CONECT    6    8   11                                                       
CONECT    7    5   12                                                       
CONECT    8    6   13                                                       
CONECT    9   12   14                                                       
CONECT   10    2    5   13                                                  
CONECT   11    3    6   14                                                  
CONECT   12    4    7    9                                                  
CONECT   13    8   10   14                                                  
CONECT   14    9   11   13                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for NP0048518 (1,4-Dimethyl-7-ethylazulene)
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SMILES for NP0048518 (1,4-Dimethyl-7-ethylazulene)
CCC1=CC2=C(C)C=CC2=C(C)C=C1
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INCHI for NP0048518 (1,4-Dimethyl-7-ethylazulene)
InChI=1S/C14H16/c1-4-12-7-5-10(2)13-8-6-11(3)14(13)9-12/h5-9H,4H2,1-3H3
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Synonyms
ValueSource
1,4-Dimethyl-7-ethyl-azuleneHMDB
7-Ethyl-1,4-dimethyl-azuleneHMDB
7-Ethyl-1,4-dimethylazuleneHMDB
CamazuleneHMDB
ChamazulenHMDB
ChamazuleneHMDB
DimethulenHMDB
DimethuleneHMDB
DimethwlenHMDB
LindazuleneHMDB
Chemical FormulaC14H16
Average Mass184.2768 Da
Monoisotopic Mass184.12520 Da
IUPAC Name7-ethyl-1,4-dimethylazulene
Traditional Namechamazulene
CAS Registry Number529-05-5
SMILES
CCC1=CC2=C(C)C=CC2=C(C)C=C1
InChI Identifier
InChI=1S/C14H16/c1-4-12-7-5-10(2)13-8-6-11(3)14(13)9-12/h5-9H,4H2,1-3H3
InChI KeyGXGJIOMUZAGVEH-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea-
Achillea alpinaPlant
Achillea collinaLOTUS Database
Achillea millefoliumPlant
Achillea moschataPlant
Achillea,Artemisia spp.-
Artemisia absinthiumPlant
Artemisia arborescensLOTUS Database
Artemisia argyiLOTUS Database
Artemisia jacuticaLOTUS Database
Artemisia macrocephalaLOTUS Database
Artemisia spp.Plant
Artemisia thusculaLOTUS Database
Chamaemalum nobile-
Chamaemelum nobileFooDB
Chamomilla rectitaPlant
Chamomilla recutinaPlant
Leonurus sibiricusLOTUS Database
Lindera aggregataPlant
Matricaria chamomillaPlant
Matricaria recutitaFooDB
Nepeta leucophyllaPlant
Pimpinella anisumFooDB
Pinus eldaricaPlant
Pinus kochianaPlant
Pinus pallasianaPlant
Pinus sosnowskyiPlant
Pinus sylvestris L.var.sylvestris.Plant
Rhanterium epapposumLOTUS Database
Skimmia laureolaPlant
Stevia serrataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentGuaianes  
Alternative Parents
Substituents
  • Guaiane sesquiterpenoid
    • 

  • Azulene
    • 

  • Aromatic hydrocarbon
    • 

  • Polycyclic hydrocarbon
    • 

  • Unsaturated hydrocarbon
    • 

  • Hydrocarbon
    • 

  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic 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
logP4.8ALOGPS
logP4.95ChemAxon
logS-2.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity62.23 m³·mol⁻¹ChemAxon
Polarizability23.05 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0036470  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015363  
KNApSAcK IDC00003114  
Chemspider ID10268  
KEGG Compound IDC09633  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10719  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References