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Showing NP-Card for Cadalene (NP0046683)

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Record Information
Version2.0
Created at2022-03-17 20:11:09 UTC
Updated at2022-03-17 20:11:09 UTC
NP-MRD IDNP0046683
Secondary Accession NumbersNone
Natural Product Identification
Common NameCadalene
DescriptionCadalene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, cadalene is considered to be an isoprenoid lipid molecule. Cadalene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Cadalene has been detected, but not quantified in, several different foods, such as anises, cloves, figs, rosemaries, and sugar apples. This could make cadalene a potential biomarker for the consumption of these foods. The ratio of retene to cadalene in sediments can reveal the ratio of the genus Pinaceae in the biosphere. Cadalene, together with retene, simonellite and ip-iHMN, is a biomarker of higher plants, which makes it useful for paleobotanic analysis of rock sediments. It is derived from generic sesquiterpenes, and ubiquitous in essential oils of many higher plants. Cadalene is found in Abies sibirica, Bazzania japonica, Bazzania trilobata, Boenninghausenia albiflora, Calypogeia muelleriana, Cinnamomum illicioides, Cinnamomum parthenoxylon, Cinnamomum verum, Cistus creticus, Cyperus rotundus , Dictyopteris divaricata, Acca sellowiana, Hamamelis virginiana, Heterotheca grandiflora, Heterotheca subaxillaris, Hexalobus crispiflorus, Humulus lupulus, Juniperus formosana, Lavandula angustifolia, Lophocolea heterophylla, Magnolia obovata, Micromeria cristata, Rhaponticum carthamoides , Teucrium oxylepis and Xylopia aromatica. Cadalene (4-isopropyl-1,6-dimethylnaphthalene) is a polycyclic aromatic hydrocarbon with a chemical formula C15H18 and a cadinane skeleton.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046683 (Cadalene)


  Mrv0541 02241220592D          

 15 16  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
  8 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
Download

3D MOL for NP0046683 (Cadalene)

Download
3D SDF for NP0046683 (Cadalene)

  Mrv0541 02241220592D          

 15 16  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 11  1  0  0  0  0
  8 12  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046683

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=C2C=C(C)C=CC2=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H18/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5-10H,1-4H3

> <INCHI_KEY>
VMOJIHDTVZTGDO-UHFFFAOYSA-N

> <FORMULA>
C15H18

> <MOLECULAR_WEIGHT>
198.3034

> <EXACT_MASS>
198.140850576

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
24.859004939866452

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,6-dimethyl-4-(propan-2-yl)naphthalene

> <ALOGPS_LOGP>
5.70

> <JCHEM_LOGP>
5.234574501999999

> <ALOGPS_LOGS>
-6.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
66.7814

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.74e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cadalene

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0046683 (Cadalene)
Download
PDB for NP0046683 (Cadalene)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10    2                                                       
CONECT   12    8                                                            
CONECT   13    5   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

Download
3D PDB for NP0046683 (Cadalene)
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SMILES for NP0046683 (Cadalene)
CC(C)C1=C2C=C(C)C=CC2=C(C)C=C1
Download
INCHI for NP0046683 (Cadalene)
InChI=1S/C15H18/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5-10H,1-4H3
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H18
Average Mass198.3034 Da
Monoisotopic Mass198.14085 Da
IUPAC Name1,6-dimethyl-4-(propan-2-yl)naphthalene
Traditional Namecadalene
CAS Registry NumberNot Available
SMILES
CC(C)C1=C2C=C(C)C=CC2=C(C)C=C1
InChI Identifier
InChI=1S/C15H18/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5-10H,1-4H3
InChI KeyVMOJIHDTVZTGDO-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abies sibiricaPlant
Annona squamosaFooDB
Bazzania japonicaLOTUS Database
Bazzania trilobataLOTUS Database
Boenninghausenia albifloraLOTUS Database
Calypogeia muellerianaLOTUS Database
Cinnamomum illicioidesPlant
Cinnamomum parthenoxylonLOTUS Database
Cinnamomum verumLOTUS Database
Cistus creticusPlant
Cyperus rotundusPlant
Dictyopteris divaricataChromalveolata
Feijoa sellowianaPlant
Ficus caricaFooDB
Hamamelis virginianaLOTUS Database
Heterotheca grandifloraLOTUS Database
Heterotheca subaxillarisLOTUS Database
Hexalobus crispiflorusLOTUS Database
Humulus lupulusLOTUS Database
Juniperus formosanaLOTUS Database
Lavandula angustifoliaLOTUS Database
Lophocolea heterophyllaLOTUS Database
Magnolia obovataLOTUS Database
Micromeria cristataLOTUS Database
Pimpinella anisumFooDB
Rhaponticum carthamoidesPlant
Salvia rosmarinusFooDB
Syzygium aromaticumFooDB
Teucrium oxylepisLOTUS Database
Xylopia aromaticaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentSesquiterpenoids  
Alternative Parents
Substituents
  • Sesquiterpenoid
    • 

  • Cadinane sesquiterpenoid
    • 

  • Naphthalene
    • 

  • Benzenoid
    • 

  • 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
logP5.7ALOGPS
logP5.23ChemAxon
logS-6.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.78 m³·mol⁻¹ChemAxon
Polarizability24.86 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0059698  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005459  
KNApSAcK IDNot Available
Chemspider ID9808  
KEGG Compound IDNot Available
BioCyc IDCPD-8806  
BiGG IDNot Available
Wikipedia LinkCadalene  
METLIN IDNot Available
PubChem Compound10225  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References