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Showing NP-Card for Dehydrofukinone (NP0046361)

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Record Information
Version2.0
Created at2022-03-17 19:56:47 UTC
Updated at2022-03-17 19:56:47 UTC
NP-MRD IDNP0046361
Secondary Accession NumbersNone
Natural Product Identification
Common NameDehydrofukinone
DescriptionDehydrofukinone belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Dehydrofukinone is found in Cacalia hastata, Ligularia kanaitzensis, Ligularia subspicata, Petasites hybridus , Packera aurea, Senecio glaucus, Senecio suaveolens and Tephroseris integrifolia. Dehydrofukinone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046361 (Dehydrofukinone)


  Mrv0541 02241212582D          

 16 17  0  0  0  0            999 V2000
   -2.0920   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8064   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8064   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0920   -2.6223    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3775   -2.2098    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3775   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6630   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6630   -2.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0514   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0514   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659   -0.9723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659   -2.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4804   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659   -3.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3775   -3.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0920   -3.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  7  6  2  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  5 15  1  1  0  0  0
  4 16  1  1  0  0  0
M  END
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3D MOL for NP0046361 (Dehydrofukinone)

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3D SDF for NP0046361 (Dehydrofukinone)

  Mrv0541 02241212582D          

 16 17  0  0  0  0            999 V2000
   -2.0920   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8064   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8064   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0920   -2.6223    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3775   -2.2098    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3775   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6630   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6630   -2.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0514   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0514   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659   -0.9723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659   -2.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4804   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659   -3.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3775   -3.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0920   -3.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  7  6  2  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  5 15  1  1  0  0  0
  4 16  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0046361

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1CCCC2=CC(=O)C(C[C@]12C)=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O/c1-10(2)13-9-15(4)11(3)6-5-7-12(15)8-14(13)16/h8,11H,5-7,9H2,1-4H3/t11-,15+/m0/s1

> <INCHI_KEY>
DZOKWSREAZGFFC-XHDPSFHLSA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.3346

> <EXACT_MASS>
218.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.129328312798208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aR,5S)-4a,5-dimethyl-3-(propan-2-ylidene)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
4.110179681666667

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.300940482888244

> <JCHEM_PKA_STRONGEST_BASIC>
-4.330450878242347

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
68.9282

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,5S)-4a,5-dimethyl-3-(propan-2-ylidene)-5,6,7,8-tetrahydro-4H-naphthalen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0046361 (Dehydrofukinone)
Download
PDB for NP0046361 (Dehydrofukinone)
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      -3.905  -1.815   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.239  -2.585   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.239  -4.125   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.905  -4.895   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.571  -4.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.571  -2.585   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.238  -1.815   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.238  -4.895   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.096  -4.125   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.096  -2.585   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.430  -1.815   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.430  -4.895   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.763  -4.125   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.430  -6.435   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.571  -5.665   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.905  -6.435   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6    8   15                                             
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    5                                                            
CONECT   16    4                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

Download
3D PDB for NP0046361 (Dehydrofukinone)
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SMILES for NP0046361 (Dehydrofukinone)
C[C@H]1CCCC2=CC(=O)C(C[C@]12C)=C(C)C
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INCHI for NP0046361 (Dehydrofukinone)
InChI=1S/C15H22O/c1-10(2)13-9-15(4)11(3)6-5-7-12(15)8-14(13)16/h8,11H,5-7,9H2,1-4H3/t11-,15+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H22O
Average Mass218.3346 Da
Monoisotopic Mass218.16707 Da
IUPAC Name(4aR,5S)-4a,5-dimethyl-3-(propan-2-ylidene)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one
Traditional Name(4aR,5S)-4a,5-dimethyl-3-(propan-2-ylidene)-5,6,7,8-tetrahydro-4H-naphthalen-2-one
CAS Registry NumberNot Available
SMILES
C[C@H]1CCCC2=CC(=O)C(C[C@]12C)=C(C)C
InChI Identifier
InChI=1S/C15H22O/c1-10(2)13-9-15(4)11(3)6-5-7-12(15)8-14(13)16/h8,11H,5-7,9H2,1-4H3/t11-,15+/m0/s1
InChI KeyDZOKWSREAZGFFC-XHDPSFHLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Arctium lappaFooDB
Cacalia hastataPlant
Ligularia kanaitzensisLOTUS Database
Ligularia subspicataLOTUS Database
Petasites hybridusPlant
Senecio aureusLOTUS Database
Senecio glaucusLOTUS Database
Senecio suaveolensLOTUS Database
Tephroseris integrifoliaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassSesquiterpenoids  
Direct ParentEremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids  
Alternative Parents
Substituents
  • Eremophilane sesquiterpenoid
    • 

  • Quinomethane
    • 

  • O-quinomethane
    • 

  • Cyclohexenone
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP3.99ALOGPS
logP4.11ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)19.3ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity68.93 m³·mol⁻¹ChemAxon
Polarizability26.13 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004100  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound177072  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available