NP-MRD: Showing NP-Card for methyl (2e,7e)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-2,7-diene-8-carboxylate (NP0242935)

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Record Information

Version

2.0

Created at

2022-09-07 03:22:52 UTC

Updated at

2022-09-07 03:22:52 UTC

NP-MRD ID

NP0242935

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2e,7e)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-2,7-diene-8-carboxylate

Description

MELAMPODININ 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. methyl (2e,7e)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-2,7-diene-8-carboxylate is found in Melampodium diffusum. Based on a literature review very few articles have been published on MELAMPODININ.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072205222D          

 37 39  0  0  0  0            999 V2000
    2.3513   -0.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0782    0.4579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7760    1.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0107    1.6014    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4127    1.7502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1084    1.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9034    1.5271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4917    0.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6907    0.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2868    1.1691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0818    1.3894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8751    0.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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  6 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309072205222D          

 37 39  0  0  0  0            999 V2000
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 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 36  2  0  0  0  0
 24 37  1  0  0  0  0
  2 37  1  0  0  0  0
  6 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242935

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C/C2OC2\C(C)=C\C2OC(=O)C(=C)C2C(OC(=O)C(C)(O)C(C)OC(C)=O)C\1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O12/c1-10-8-16-18(11(2)22(28)36-16)21(37-24(30)25(6,31)12(3)33-13(4)26)20(34-14(5)27)15(23(29)32-7)9-17-19(10)35-17/h8-9,12,16-21,31H,2H2,1,3-7H3/b10-8+,15-9+

> <INCHI_KEY>
MMVDOOAKJHDAMB-BPNXTJCCSA-N

> <FORMULA>
C25H30O12

> <MOLECULAR_WEIGHT>
522.503

> <EXACT_MASS>
522.173726406

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
49.960188271421714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2E,7E)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0^{4,6}]tetradeca-2,7-diene-8-carboxylate

> <JCHEM_LOGP>
1.0121484176666662

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.639849627635789

> <JCHEM_PKA_STRONGEST_BASIC>
-4.260735227960517

> <JCHEM_POLAR_SURFACE_AREA>
164.26

> <JCHEM_REFRACTIVITY>
122.7502

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E,7E)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0^{4,6}]tetradeca-2,7-diene-8-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       4.389  -0.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.746   0.855   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.182   2.288   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.753   2.989   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       6.370   3.267   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       7.669   2.439   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.153   2.851   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.251   1.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.756   1.401   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.735   2.182   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      13.219   2.593   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.834   1.103   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.448  -0.388   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.964  -0.800   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.558  -2.802   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.925  -4.337   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      12.609  -4.151   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.636  -5.763   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.865   0.280   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.594  -1.328   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.434  -2.562   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.121  -1.949   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.459  -3.823   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.381  -0.131   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.952  -1.389   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.571  -2.474   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.342  -1.453   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.146  -4.096   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.552  -4.138   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.080  -5.419   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.504  -5.563   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.973  -5.734   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.417  -6.803   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       4.800  -8.214   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.713  -9.454   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.269  -8.385   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.283   0.948   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   37                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   37                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10   12                                                       
CONECT   12   11   10   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   14   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19   25   37                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30   31                                             
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
CONECT   37   24    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₀O₁₂

Average Mass

522.5030 Da

Monoisotopic Mass

522.17373 Da

IUPAC Name

methyl (2E,7E)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0^{4,6}]tetradeca-2,7-diene-8-carboxylate

Traditional Name

methyl (2E,7E)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0^{4,6}]tetradeca-2,7-diene-8-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C/C2OC2\C(C)=C\C2OC(=O)C(=C)C2C(OC(=O)C(C)(O)C(C)OC(C)=O)C\1OC(C)=O

InChI Identifier

InChI=1S/C25H30O12/c1-10-8-16-18(11(2)22(28)36-16)21(37-24(30)25(6,31)12(3)33-13(4)26)20(34-14(5)27)15(23(29)32-7)9-17-19(10)35-17/h8-9,12,16-21,31H,2H2,1,3-7H3/b10-8+,15-9+

InChI Key

MMVDOOAKJHDAMB-BPNXTJCCSA-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
Melampodium diffusum	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
Pentacarboxylic acid or derivatives
Sesquiterpenoid
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Tertiary alcohol
Tetrahydrofuran
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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	1.01	ChemAxon
pKa (Strongest Acidic)	11.64	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	164.26 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	122.75 m³·mol⁻¹	ChemAxon
Polarizability	49.96 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00003323

Chemspider ID

4514074

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5359028

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2e,7e)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-2,7-diene-8-carboxylate (NP0242935)

MOL for NP0242935 (methyl (2e,7e)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-2,7-diene-8-carboxylate)

3D MOL for NP0242935 (methyl (2e,7e)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-2,7-diene-8-carboxylate)

3D SDF for NP0242935 (methyl (2e,7e)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-2,7-diene-8-carboxylate)

3D-SDF for NP0242935 (methyl (2e,7e)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-2,7-diene-8-carboxylate)

PDB for NP0242935 (methyl (2e,7e)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-2,7-diene-8-carboxylate)

3D PDB for NP0242935 (methyl (2e,7e)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-2,7-diene-8-carboxylate)

SMILES for NP0242935 (methyl (2e,7e)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-2,7-diene-8-carboxylate)

INCHI for NP0242935 (methyl (2e,7e)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-2,7-diene-8-carboxylate)

Structure for NP0242935 (methyl (2e,7e)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-2,7-diene-8-carboxylate)

3D Structure for NP0242935 (methyl (2e,7e)-9-(acetyloxy)-10-{[3-(acetyloxy)-2-hydroxy-2-methylbutanoyl]oxy}-3-methyl-12-methylidene-13-oxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-2,7-diene-8-carboxylate)