NP-MRD: Showing NP-Card for 4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate (NP0213221)

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Record Information

Version

2.0

Created at

2022-09-05 12:08:27 UTC

Updated at

2022-09-05 12:08:28 UTC

NP-MRD ID

NP0213221

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate

Description

4,9-Dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]Tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate 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. 4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate is found in Dendroviguiera puruana. 4,9-Dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]Tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231520402D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004231520402D          

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M  END
> <DATABASE_ID>
NP0213221

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)OC1CC2OC2(C)CC(OC(=O)C2(C)OC2C)C2C(OC(=O)C2=C)C=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O8/c1-8-12(2)21(26)29-16-10-19-24(6,33-19)11-18(31-23(28)25(7)15(5)32-25)20-14(4)22(27)30-17(20)9-13(16)3/h9,12,15-20H,4,8,10-11H2,1-3,5-7H3

> <INCHI_KEY>
DABPASAPXTUCCU-UHFFFAOYSA-N

> <FORMULA>
C25H34O8

> <MOLECULAR_WEIGHT>
462.539

> <EXACT_MASS>
462.225368055

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
49.05559547769875

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
3.479816582999999

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.588596568411923

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9580679854165175

> <JCHEM_POLAR_SURFACE_AREA>
103.96000000000001

> <JCHEM_REFRACTIVITY>
117.17310000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       9.365   9.492   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.750   8.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.652   6.922   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.168   7.333   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.038   5.431   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.940   4.351   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      10.522   5.020   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      10.908   3.529   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.392   3.118   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.778   1.627   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      13.164   0.136   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      11.680   0.547   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.269  -0.937   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.196   0.958   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.098  -0.121   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.483  -1.612   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.385  -2.692   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.901  -2.280   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.771  -4.182   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.306  -4.061   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.370  -4.821   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.624  -5.715   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.263  -7.117   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.613   0.290   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.228   1.781   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.690   1.875   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.126   0.442   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       3.635   0.056   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.315  -0.538   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.221  -2.075   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.326   2.861   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.810   2.449   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.246   1.016   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   32                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10   12                                                       
CONECT   12   11   10   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   19   23                                                  
CONECT   23   22                                                            
CONECT   24   15   25   29                                                  
CONECT   25   24   26   31                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   24   30                                                  
CONECT   30   29                                                            
CONECT   31   25   32                                                       
CONECT   32   31    8   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
4,9-Dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0,]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylic acid	Generator
4,9-Dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylic acid	Generator

Chemical Formula

C₂₅H₃₄O₈

Average Mass

462.5390 Da

Monoisotopic Mass

462.22537 Da

IUPAC Name

4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate

Traditional Name

4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)OC1CC2OC2(C)CC(OC(=O)C2(C)OC2C)C2C(OC(=O)C2=C)C=C1C

InChI Identifier

InChI=1S/C25H34O8/c1-8-12(2)21(26)29-16-10-19-24(6,33-19)11-18(31-23(28)25(7)15(5)32-25)20-14(4)22(27)30-17(20)9-13(16)3/h9,12,15-20H,4,8,10-11H2,1-3,5-7H3

InChI Key

DABPASAPXTUCCU-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dendroviguiera puruana	LOTUS Database	35616633

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.

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
Sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Gamma butyrolactone
Oxirane carboxylic acid
Fatty acyl
Oxirane carboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Tetrahydrofuran
Enoate ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	2.71	ALOGPS
logP	3.48	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	19.59	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	103.96 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	117.17 m³·mol⁻¹	ChemAxon
Polarizability	49.06 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

LOTUS database [Link]

Showing NP-Card for 4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate (NP0213221)

MOL for NP0213221 (4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate)

3D MOL for NP0213221 (4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate)

3D SDF for NP0213221 (4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate)

3D-SDF for NP0213221 (4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate)

PDB for NP0213221 (4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate)

3D PDB for NP0213221 (4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate)

SMILES for NP0213221 (4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate)

INCHI for NP0213221 (4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate)

Structure for NP0213221 (4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate)

3D Structure for NP0213221 (4,9-dimethyl-8-[(2-methylbutanoyl)oxy]-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl 2,3-dimethyloxirane-2-carboxylate)