NP-MRD: Showing NP-Card for 5-[(3-hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate (NP0247347)

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Record Information

Version

2.0

Created at

2022-09-07 09:10:30 UTC

Updated at

2022-09-07 09:10:30 UTC

NP-MRD ID

NP0247347

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(3-hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate

Description

5-[(3-Hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-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. 5-[(3-Hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-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


  Mrv1533004171519572D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004171519572D          

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 17 18  1  0  0  0  0
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 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 18 27  1  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 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
 33 35  1  0  0  0  0
  9 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247347

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CCCC(C)=CC2OC(=O)C(=C)C2C(OC(=O)C2(C)OC2C)C1OC(=O)C(C)C(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C26H34O10/c1-12-9-8-10-17(24(30)32-7)20(34-22(28)13(2)15(4)27)21(35-25(31)26(6)16(5)36-26)19-14(3)23(29)33-18(19)11-12/h10-11,13,15-16,18-21,27H,3,8-9H2,1-2,4-7H3

> <INCHI_KEY>
LRTMGMWLZYDWGF-UHFFFAOYSA-N

> <FORMULA>
C26H34O10

> <MOLECULAR_WEIGHT>
506.548

> <EXACT_MASS>
506.215197295

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.01386713999433

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(3-hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
3.100156214666667

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.693445822211284

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.027367967149225

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7867882565965267

> <JCHEM_POLAR_SURFACE_AREA>
137.96

> <JCHEM_REFRACTIVITY>
126.2706

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(3-hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       2.119  -5.992   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.303  -4.562   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.291  -3.230   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.852  -2.944   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.675  -2.796   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.829  -4.328   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.233  -4.961   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.483  -4.061   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.329  -2.529   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.578  -1.629   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.424  -0.097   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.460   1.043   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.695   2.380   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -6.697   3.630   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.188   2.067   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.703   3.619   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.020   0.536   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.770  -0.364   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.752   1.012   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.406   2.556   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.384   3.860   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.192   2.433   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.888   2.436   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.187   3.926   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.295   3.508   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.788   3.887   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.924  -1.896   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.312  -2.262   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.291  -2.186   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.495  -3.835   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       1.817  -1.552   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.644  -0.124   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.618  -2.186   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.183  -2.689   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.010  -1.269   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -3.972  -0.858   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   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   36                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   11   18                                                  
CONECT   18   17   19   27                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   22   26                                                  
CONECT   26   25                                                            
CONECT   27   18    5   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36    9                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
5-[(3-Hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylic acid	Generator

Chemical Formula

C₂₆H₃₄O₁₀

Average Mass

506.5480 Da

Monoisotopic Mass

506.21520 Da

IUPAC Name

5-[(3-hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate

Traditional Name

5-[(3-hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CCCC(C)=CC2OC(=O)C(=C)C2C(OC(=O)C2(C)OC2C)C1OC(=O)C(C)C(C)O

InChI Identifier

InChI=1S/C26H34O10/c1-12-9-8-10-17(24(30)32-7)20(34-22(28)13(2)15(4)27)21(35-25(31)26(6)16(5)36-26)19-14(3)23(29)33-18(19)11-12/h10-11,13,15-16,18-21,27H,3,8-9H2,1-2,4-7H3

InChI Key

LRTMGMWLZYDWGF-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

Not Available

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
Germacrane sesquiterpenoid
Tetracarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Hydroxy acid
Oxirane carboxylic acid
Oxirane carboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Tetrahydrofuran
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
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	2.28	ALOGPS
logP	3.1	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	15.03	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	137.96 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	126.27 m³·mol⁻¹	ChemAxon
Polarizability	51.01 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

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 5-[(3-hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate (NP0247347)

MOL for NP0247347 (5-[(3-hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

3D MOL for NP0247347 (5-[(3-hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

3D SDF for NP0247347 (5-[(3-hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

3D-SDF for NP0247347 (5-[(3-hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

PDB for NP0247347 (5-[(3-hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

3D PDB for NP0247347 (5-[(3-hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

SMILES for NP0247347 (5-[(3-hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

INCHI for NP0247347 (5-[(3-hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

Structure for NP0247347 (5-[(3-hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)

3D Structure for NP0247347 (5-[(3-hydroxy-2-methylbutanoyl)oxy]-6-(methoxycarbonyl)-10-methyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-4-yl 2,3-dimethyloxirane-2-carboxylate)