NP-MRD: Showing NP-Card for methyl 11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-5-(sec-butoxy)-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate (NP0240741)

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Record Information

Version

2.0

Created at

2022-09-07 00:38:06 UTC

Updated at

2022-09-07 00:38:06 UTC

NP-MRD ID

NP0240741

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-5-(sec-butoxy)-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate

Description

Methyl 5-(butan-2-yloxy)-11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-6-carboxylate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. methyl 11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-5-(sec-butoxy)-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate is found in Tetragonotheca repanda. Methyl 5-(butan-2-yloxy)-11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-6-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191522382D          

 33 34  0  0  0  0            999 V2000
    2.2588   -2.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5501   -1.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0273   -0.9781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2132   -1.1117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3186   -0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7958    0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9817    0.2983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6904   -0.4735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1237   -0.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6465    0.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4150   -1.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2291   -1.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5204   -2.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1078   -2.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589    0.9365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7502    1.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1061    2.2240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5643    1.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3624    1.6330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6697    2.7476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925    2.1093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9012    1.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4240    0.6993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9468    0.0611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  3  4  1  0  0  0  0
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  7 15  1  0  0  0  0
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  6 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
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 32 33  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004191522382D          

 33 34  0  0  0  0            999 V2000
    2.2588   -2.3882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5501   -1.6163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3624    1.6330    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0240741

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)OC1C(OC(=O)C(C)=CC)C2C(OC(=O)C2=C)C(O)C(=C)CCC=C1C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O8/c1-8-13(3)23(27)33-22-18-16(6)24(28)32-21(18)19(26)14(4)11-10-12-17(25(29)30-7)20(22)31-15(5)9-2/h8,12,15,18-22,26H,4,6,9-11H2,1-3,5,7H3

> <INCHI_KEY>
VTHHRGFEWZEQAC-UHFFFAOYSA-N

> <FORMULA>
C25H34O8

> <MOLECULAR_WEIGHT>
462.539

> <EXACT_MASS>
462.225368055

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
48.76878136497968

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 5-(butan-2-yloxy)-11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-6-carboxylate

> <ALOGPS_LOGP>
3.45

> <JCHEM_LOGP>
4.257927863999999

> <ALOGPS_LOGS>
-3.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.267322215508546

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.581315362806702

> <JCHEM_PKA_STRONGEST_BASIC>
-3.419329917100418

> <JCHEM_POLAR_SURFACE_AREA>
108.36

> <JCHEM_REFRACTIVITY>
121.77229999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-5-(sec-butoxy)-3aH,4H,5H,8H,9H,11H,11aH-cyclodeca[b]furan-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       4.216  -4.458   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.760  -3.017   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.784  -1.826   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.265  -2.075   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.328  -0.385   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.352   0.806   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.832   0.557   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.289  -0.884   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.231  -1.133   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.207   0.058   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.775  -2.574   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.294  -2.824   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.838  -4.264   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.201  -3.766   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.857   1.748   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.400   3.189   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.198   4.151   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.089   3.305   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.529   3.849   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.682   1.820   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.644   0.618   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.920   3.438   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.410   3.048   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.464   4.879   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.488   6.071   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.983   5.129   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.959   3.937   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.416   2.497   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.896   2.247   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.872   1.056   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.279  -0.429   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.391   1.305   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       7.367   0.114   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                                                       
CONECT    6    5    7   29                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11                                                            
CONECT   15    7   16   20                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   15   21                                                  
CONECT   21   20                                                            
CONECT   22   16   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    6   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

View in JSmol

Synonyms

Value	Source
Methyl 5-(butan-2-yloxy)-11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,10H,11H,11ah-cyclodeca[b]furan-6-carboxylic acid	Generator

Chemical Formula

C₂₅H₃₄O₈

Average Mass

462.5390 Da

Monoisotopic Mass

462.22537 Da

IUPAC Name

methyl 5-(butan-2-yloxy)-11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-6-carboxylate

Traditional Name

methyl 11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-5-(sec-butoxy)-3aH,4H,5H,8H,9H,11H,11aH-cyclodeca[b]furan-6-carboxylate

CAS Registry Number

Not Available

SMILES

CCC(C)OC1C(OC(=O)C(C)=CC)C2C(OC(=O)C2=C)C(O)C(=C)CCC=C1C(=O)OC

InChI Identifier

InChI=1S/C25H34O8/c1-8-13(3)23(27)33-22-18-16(6)24(28)32-21(18)19(26)14(4)11-10-12-17(25(29)30-7)20(22)31-15(5)9-2/h8,12,15,18-22,26H,4,6,9-11H2,1-3,5,7H3

InChI Key

VTHHRGFEWZEQAC-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
Tetragonotheca repanda	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Germacrane sesquiterpenoid
Sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Tetrahydrofuran
Alpha,beta-unsaturated carboxylic ester
Methyl ester
Enoate ester
Secondary alcohol
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
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	3.45	ALOGPS
logP	4.26	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	13.58	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	108.36 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	121.77 m³·mol⁻¹	ChemAxon
Polarizability	48.77 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

LOTUS database [Link]

Showing NP-Card for methyl 11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-5-(sec-butoxy)-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate (NP0240741)

MOL for NP0240741 (methyl 11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-5-(sec-butoxy)-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

3D MOL for NP0240741 (methyl 11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-5-(sec-butoxy)-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

3D SDF for NP0240741 (methyl 11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-5-(sec-butoxy)-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

3D-SDF for NP0240741 (methyl 11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-5-(sec-butoxy)-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

PDB for NP0240741 (methyl 11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-5-(sec-butoxy)-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

3D PDB for NP0240741 (methyl 11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-5-(sec-butoxy)-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

SMILES for NP0240741 (methyl 11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-5-(sec-butoxy)-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

INCHI for NP0240741 (methyl 11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-5-(sec-butoxy)-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

Structure for NP0240741 (methyl 11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-5-(sec-butoxy)-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)

3D Structure for NP0240741 (methyl 11-hydroxy-4-[(2-methylbut-2-enoyl)oxy]-3,10-dimethylidene-2-oxo-5-(sec-butoxy)-3ah,4h,5h,8h,9h,11h,11ah-cyclodeca[b]furan-6-carboxylate)