NP-MRD: Showing NP-Card for (1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide (NP0335649)

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Record Information

Version

2.0

Created at

2024-09-11 02:35:06 UTC

Updated at

2024-09-11 02:35:06 UTC

NP-MRD ID

NP0335649

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide

Description

(1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide 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. Based on a literature review very few articles have been published on (1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262305072D          

 24 25  0  0  0  0            999 V2000
   -2.1353   -0.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353   -0.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -1.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7080   -0.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7080   -0.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211    0.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062   -1.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191   -0.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7191   -0.0213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062    0.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1769   -2.0652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9944   -2.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3275   -1.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2952   -0.7370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062    1.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211   -2.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4073   -2.8677    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1353   -1.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7080    1.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7080    2.4547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211    1.2160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4211    2.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062    2.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7219    2.4547    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  2  0  0  0  0
  3 16  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  2  0  0  0  0
 13 18  2  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335649

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)OC1CC2C(OC(=O)C2=C)\C=C(C)\CC\C=C1/C

> <INCHI_IDENTIFIER>
InChI=1/C20H28O4/c1-6-13(3)19(21)23-17-11-16-15(5)20(22)24-18(16)10-12(2)8-7-9-14(17)4/h9-10,13,16-18H,5-8,11H2,1-4H3/b12-10+,14-9+

> <INCHI_KEY>
HNBSPEQFYAYDLE-LSBMZBKTNA-N

> <FORMULA>
C20H28O4

> <MOLECULAR_WEIGHT>
332.44

> <EXACT_MASS>
332.198759382

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
36.92095294651219

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-5-yl 2-methylbutanoate

> <JCHEM_LOGP>
4.714571780333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.6677344221184836

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
94.41579999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6,10-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-5-yl 2-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -3.986  -0.040   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.986  -1.581   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.653  -2.352   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.322  -1.581   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.322  -0.040   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.653   0.728   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.012  -2.352   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.342  -1.581   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.342  -0.040   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.012   0.728   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.330  -3.855   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.856  -4.017   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.478  -2.617   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.551  -1.376   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.012   2.270   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.653  -3.893   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.627  -5.353   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.986  -2.301   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.322   3.041   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.322   4.582   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.653   2.270   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.653   5.353   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.012   5.353   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.348   4.582   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    7                                                       
CONECT    5    6   10   14                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8   11                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    5    9   15                                                  
CONECT   11    7   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13    8   12   18                                                  
CONECT   14    5                                                            
CONECT   15   10   19                                                       
CONECT   16    3                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19   15   20   21                                                  
CONECT   20   19   22   23                                                  
CONECT   21   19                                                            
CONECT   22   20                                                            
CONECT   23   20   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₄

Average Mass

332.4400 Da

Monoisotopic Mass

332.19876 Da

IUPAC Name

6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-5-yl 2-methylbutanoate

Traditional Name

6,10-dimethyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-5-yl 2-methylbutanoate

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)OC1CC2C(OC(=O)C2=C)\C=C(C)\CC\C=C1/C

InChI Identifier

InChI=1/C20H28O4/c1-6-13(3)19(21)23-17-11-16-15(5)20(22)24-18(16)10-12(2)8-7-9-14(17)4/h9-10,13,16-18H,5-8,11H2,1-4H3/b12-10+,14-9+

InChI Key

HNBSPEQFYAYDLE-LSBMZBKTNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound 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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Germacrane sesquiterpenoid
Sesquiterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.71	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	94.42 m³·mol⁻¹	ChemAxon
Polarizability	36.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide (NP0335649)

MOL for NP0335649 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

3D MOL for NP0335649 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

3D SDF for NP0335649 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

3D-SDF for NP0335649 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

PDB for NP0335649 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

3D PDB for NP0335649 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

SMILES for NP0335649 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

INCHI for NP0335649 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

Structure for NP0335649 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)

3D Structure for NP0335649 ((1(10)E,4E,6a,9b)-9-(2-Methylbutanoyloxy)-1(10),4,11(13)-germacratrien-12,6-olide)