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Showing NP-Card for Germacranolide (NP0046362)

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Record Information
Version2.0
Created at2022-03-17 19:56:48 UTC
Updated at2022-03-17 19:56:48 UTC
NP-MRD IDNP0046362
Secondary Accession NumbersNone
Natural Product Identification
Common NameGermacranolide
DescriptionGermacranolide belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Germacranolide is found in Inula racemosa . Germacranolide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046362 (Germacranolide)


  Mrv1533007301516522D          

 19 20  0  0  0  0            999 V2000
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396    1.8646    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
    2.8579    0.8250    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
    1.4289    0.8250    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
    0.7145   -0.4125    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   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  1  1  0  0  0  0
 10  5  1  0  0  0  0
 10  7  2  0  0  0  0
 11  2  1  0  0  0  0
 11  6  2  0  0  0  0
 11  9  1  0  0  0  0
 12  3  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  1  0  0  0  0
 14  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15 12  1  0  0  0  0
 16 15  2  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18  6  1  0  0  0  0
 19  7  1  0  0  0  0
M  END
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3D MOL for NP0046362 (Germacranolide)

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3D SDF for NP0046362 (Germacranolide)

  Mrv1533007301516522D          

 19 20  0  0  0  0            999 V2000
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9440    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396    1.8646    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
    2.8579    0.8250    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
    1.4289    0.8250    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
    0.7145   -0.4125    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   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
 10  1  1  0  0  0  0
 10  5  1  0  0  0  0
 10  7  2  0  0  0  0
 11  2  1  0  0  0  0
 11  6  2  0  0  0  0
 11  9  1  0  0  0  0
 12  3  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  1  0  0  0  0
 14  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15 12  1  0  0  0  0
 16 15  2  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18  6  1  0  0  0  0
 19  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0046362

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C1=C(C)/CC2OC(=O)C(C)C2C\C([H])=C(C)\CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h6-7,12-14H,4-5,8-9H2,1-3H3/b10-7+,11-6+

> <INCHI_KEY>
QJRFOUJEGHRZIU-NXAIOARDSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.339

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.85986773156359

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6,10-trimethyl-2H,3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-2-one

> <ALOGPS_LOGP>
4.23

> <JCHEM_LOGP>
3.5186044823333336

> <ALOGPS_LOGS>
-3.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.08296359818532

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
70.297

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6,10-trimethyl-3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0046362 (Germacranolide)
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PDB for NP0046362 (Germacranolide)
HEADER    PROTEIN                                 30-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-15         0                                  
HETATM    1  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.762   1.246   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.941   3.481   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.465   2.016   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.910   0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.465  -0.476   0.000  0.00  0.00           O+0
HETATM   18  H   UNK     0       4.001  -2.310   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       4.001   0.770   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4    5    6                                                       
CONECT    5    4   10                                                       
CONECT    6    4   11   18                                                  
CONECT    7    8   10   19                                                  
CONECT    8    7   13                                                       
CONECT    9   11   14                                                       
CONECT   10    1    5    7                                                  
CONECT   11    2    6    9                                                  
CONECT   12    3   13   15                                                  
CONECT   13    8   12   14                                                  
CONECT   14    9   13   17                                                  
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   14   15                                                       
CONECT   18    6                                                            
CONECT   19    7                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

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3D PDB for NP0046362 (Germacranolide)
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SMILES for NP0046362 (Germacranolide)
[H]\C1=C(C)/CC2OC(=O)C(C)C2C\C([H])=C(C)\CC1
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INCHI for NP0046362 (Germacranolide)
InChI=1S/C15H22O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h6-7,12-14H,4-5,8-9H2,1-3H3/b10-7+,11-6+
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H22O2
Average Mass234.3390 Da
Monoisotopic Mass234.16198 Da
IUPAC Name3,6,10-trimethyl-2H,3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-2-one
Traditional Name3,6,10-trimethyl-3H,3aH,4H,7H,8H,11H,11aH-cyclodeca[b]furan-2-one
CAS Registry NumberNot Available
SMILES
[H]\C1=C(C)/CC2OC(=O)C(C)C2C\C([H])=C(C)\CC1
InChI Identifier
InChI=1S/C15H22O2/c1-10-5-4-6-11(2)9-14-13(8-7-10)12(3)15(16)17-14/h6-7,12-14H,4-5,8-9H2,1-3H3/b10-7+,11-6+
InChI KeyQJRFOUJEGHRZIU-NXAIOARDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Arctium lappaFooDB
Inula racemosaPlant
Taraxacum officinaleFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTerpene lactones  
Direct ParentGermacranolides and derivatives  
Alternative Parents
Substituents
  • Germacranolide
    • 

  • Germacrane sesquiterpenoid
    • 

  • Sesquiterpenoid
    • 

  • Gamma butyrolactone
    • 

  • Tetrahydrofuran
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • 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
logP4.23ALOGPS
logP3.52ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)-7.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity70.3 m³·mol⁻¹ChemAxon
Polarizability26.86 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 IDFDB004104  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGermacranolide  
METLIN IDNot Available
PubChem Compound91694425  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available