NP-MRD: Showing NP-Card for 2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one (NP0190962)

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Record Information

Version

2.0

Created at

2022-09-04 07:44:39 UTC

Updated at

2022-09-04 07:44:39 UTC

NP-MRD ID

NP0190962

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one

Description

2,16-Dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]Nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]Octadeca-2,4-dien-7-one belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety. 2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one is found in Datura metel. 2,16-Dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]Nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]Octadeca-2,4-dien-7-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201502122D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004201502122D          

 33 38  0  0  0  0            999 V2000
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 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0190962

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2C=CCC(=O)OC2CC2C3CCC(C4COC5(C)CC4OC(=O)C5=C)C3(C)CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O5/c1-15-17-10-11-27(3)21(19(17)12-23-18(15)6-5-7-25(29)32-23)8-9-22(27)20-14-31-28(4)13-24(20)33-26(30)16(28)2/h5-6,17,19-24H,2,7-14H2,1,3-4H3

> <INCHI_KEY>
CNWDLTNXJPRUTP-UHFFFAOYSA-N

> <FORMULA>
C28H36O5

> <MOLECULAR_WEIGHT>
452.591

> <EXACT_MASS>
452.256274259

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
50.920916372781086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one

> <ALOGPS_LOGP>
4.02

> <JCHEM_LOGP>
3.9923335436666667

> <ALOGPS_LOGS>
-5.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.199426508206978

> <JCHEM_POLAR_SURFACE_AREA>
61.830000000000005

> <JCHEM_REFRACTIVITY>
125.43869999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0      -4.028  -8.413   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.189  -7.122   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.888  -5.750   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.421  -5.899   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.494  -4.794   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.298  -3.266   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.982  -2.467   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.132  -0.934   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -3.536  -2.997   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.050  -4.458   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.512  -4.539   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.813  -5.911   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.651  -7.202   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.952  -8.575   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.586  -8.655   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.424  -7.364   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.263  -8.655   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.946  -7.123   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.186  -5.602   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.814  -4.902   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.725  -5.991   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.034  -8.212   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.445  -9.634   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.034 -11.057   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.457 -11.646   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.457 -13.186   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.954  -9.634   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.457  -7.622   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.880  -8.212   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       7.469  -9.634   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.009  -9.634   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.880 -11.057   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.969 -12.146   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    3   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   21                                                  
CONECT   13   12    2   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   21                                             
CONECT   17   16                                                            
CONECT   18   16   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   12   16                                                  
CONECT   22   18   23   28                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   32                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   22   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   25   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₆O₅

Average Mass

452.5910 Da

Monoisotopic Mass

452.25627 Da

IUPAC Name

2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one

Traditional Name

2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one

CAS Registry Number

Not Available

SMILES

CC1=C2C=CCC(=O)OC2CC2C3CCC(C4COC5(C)CC4OC(=O)C5=C)C3(C)CCC12

InChI Identifier

InChI=1S/C28H36O5/c1-15-17-10-11-27(3)21(19(17)12-23-18(15)6-5-7-25(29)32-23)8-9-22(27)20-14-31-28(4)13-24(20)33-26(30)16(28)2/h5-6,17,19-24H,2,7-14H2,1,3-4H3

InChI Key

CNWDLTNXJPRUTP-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
Datura metel	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as delta valerolactones. These are cyclic organic compounds containing an oxan-2- one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Delta valerolactones

Direct Parent

Delta valerolactones

Alternative Parents

Substituents

Delta valerolactone
Delta_valerolactone
Oxane
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxide
Organic oxygen 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	4.02	ALOGPS
logP	3.99	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	125.44 m³·mol⁻¹	ChemAxon
Polarizability	50.92 Å³	ChemAxon
Number of Rings	6	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

73324094

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one (NP0190962)

MOL for NP0190962 (2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one)

3D MOL for NP0190962 (2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one)

3D SDF for NP0190962 (2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one)

3D-SDF for NP0190962 (2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one)

PDB for NP0190962 (2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one)

3D PDB for NP0190962 (2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one)

SMILES for NP0190962 (2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one)

INCHI for NP0190962 (2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one)

Structure for NP0190962 (2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one)

3D Structure for NP0190962 (2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one)