NP-MRD: Showing NP-Card for 7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate (NP0155781)

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Record Information

Version

2.0

Created at

2022-09-02 12:54:18 UTC

Updated at

2022-09-02 12:54:18 UTC

NP-MRD ID

NP0155781

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate

Description

7,7A-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl 3-methylbutanoate belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate is found in Petasites formosanus. 7,7A-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl 3-methylbutanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191523182D          

 30 32  0  0  0  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3260   -1.7269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1854   -2.6145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8499   -3.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0294   -3.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4774   -3.8951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6704   -3.7235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4155   -2.9389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1184   -4.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3733   -5.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114   -4.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6704   -3.4544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1274   -4.6739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7074   -4.2934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 66 68  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1533004191523182D          

 30 32  0  0  0  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0155781

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)OC1CCC(C)C2(C)CC3(C(OC(=O)C(C)C)C12)C(=C)COC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O6/c1-13(2)10-18(25)29-17-9-8-15(5)23(7)12-24(16(6)11-28-22(24)27)20(19(17)23)30-21(26)14(3)4/h13-15,17,19-20H,6,8-12H2,1-5,7H3

> <INCHI_KEY>
QPPZUSYMBUPRGY-UHFFFAOYSA-N

> <FORMULA>
C24H36O6

> <MOLECULAR_WEIGHT>
420.546

> <EXACT_MASS>
420.251188879

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
45.96985047232923

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl 3-methylbutanoate

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
4.415637312333336

> <ALOGPS_LOGS>
-5.18

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.626410482480138

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
110.76629999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-hexahydro-1H-spiro[indene-2,3'-oxolane]-4-yl 3-methylbutanoate

> <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      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.075  -3.224   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.813  -4.880   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.186  -6.287   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.655  -6.126   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.624  -7.271   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.118  -6.951   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.642  -5.486   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.088  -8.095   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.564  -9.560   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.581  -7.775   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.718  -6.448   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.748  -5.304   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.038  -7.955   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.705  -8.725   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.560  -7.694   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.054  -8.014   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   24                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   24                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   25   29                                             
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   17    8   13                                                  
CONECT   25   16   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   16   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
7,7a-Dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl 3-methylbutanoic acid	Generator

Chemical Formula

C₂₄H₃₆O₆

Average Mass

420.5460 Da

Monoisotopic Mass

420.25119 Da

IUPAC Name

7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-octahydrospiro[indene-2,3'-oxolane]-4-yl 3-methylbutanoate

Traditional Name

7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-hexahydro-1H-spiro[indene-2,3'-oxolane]-4-yl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)OC1CCC(C)C2(C)CC3(C(OC(=O)C(C)C)C12)C(=C)COC3=O

InChI Identifier

InChI=1S/C24H36O6/c1-13(2)10-18(25)29-17-9-8-15(5)23(7)12-24(16(6)11-28-22(24)27)20(19(17)23)30-21(26)14(3)4/h13-15,17,19-20H,6,8-12H2,1-5,7H3

InChI Key

QPPZUSYMBUPRGY-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
Petasites formosanus	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
Sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Gamma butyrolactone
Tetrahydrofuran
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen 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	3.47	ALOGPS
logP	4.42	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	110.77 m³·mol⁻¹	ChemAxon
Polarizability	45.97 Å³	ChemAxon
Number of Rings	3	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

85243281

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate (NP0155781)

MOL for NP0155781 (7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

3D MOL for NP0155781 (7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

3D SDF for NP0155781 (7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

3D-SDF for NP0155781 (7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

PDB for NP0155781 (7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

3D PDB for NP0155781 (7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

SMILES for NP0155781 (7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

INCHI for NP0155781 (7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

Structure for NP0155781 (7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)

3D Structure for NP0155781 (7,7a-dimethyl-4'-methylidene-3-[(2-methylpropanoyl)oxy]-2'-oxo-hexahydro-1h-spiro[indene-2,3'-oxolan]-4-yl 3-methylbutanoate)