NP-MRD: Showing NP-Card for 17-hydroxy-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 (NP0207080)

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Record Information

Version

2.0

Created at

2022-09-05 03:33:17 UTC

Updated at

2022-09-05 03:33:17 UTC

NP-MRD ID

NP0207080

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17-hydroxy-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

17-Hydroxy-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. 17-hydroxy-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. 17-Hydroxy-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


  Mrv1533004241513392D          

 34 39  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241513392D          

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 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 12 22  1  0  0  0  0
 17 22  1  0  0  0  0
 19 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0207080

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C2C=CCC(=O)OC2CC2C3CCC(C4COC5(C)CC4OC(=O)C5=C)C3(C)C(O)CC12

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O6/c1-14-16-6-5-7-25(30)33-22(16)10-18-17(14)11-24(29)28(4)20(18)8-9-21(28)19-13-32-27(3)12-23(19)34-26(31)15(27)2/h5-6,17-24,29H,2,7-13H2,1,3-4H3

> <INCHI_KEY>
KPKHBVCOOBDWBC-UHFFFAOYSA-N

> <FORMULA>
C28H36O6

> <MOLECULAR_WEIGHT>
468.59

> <EXACT_MASS>
468.251188879

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.406965960712206

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17-hydroxy-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>
2.57

> <JCHEM_LOGP>
2.7615224766666655

> <ALOGPS_LOGS>
-4.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3866389954324808

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
126.95419999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.69e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
17-hydroxy-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                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-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  O   UNK     0       1.285 -10.027   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.424  -7.364   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.263  -8.655   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.946  -7.123   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.186  -5.602   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.814  -4.902   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.725  -5.991   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.034  -8.212   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.445  -9.634   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.034 -11.057   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.457 -11.646   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.457 -13.186   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.954  -9.634   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.457  -7.622   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       6.880  -8.212   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.469  -9.634   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       9.009  -9.634   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.880 -11.057   0.000  0.00  0.00           C+0
HETATM   34  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   22                                                  
CONECT   13   12    2   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   22                                             
CONECT   18   17                                                            
CONECT   19   17   20   23                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   12   17                                                  
CONECT   23   19   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28   33                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   23   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   26   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₆O₆

Average Mass

468.5900 Da

Monoisotopic Mass

468.25119 Da

IUPAC Name

17-hydroxy-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

17-hydroxy-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)C(O)CC12

InChI Identifier

InChI=1S/C28H36O6/c1-14-16-6-5-7-25(30)33-22(16)10-18-17(14)11-24(29)28(4)20(18)8-9-21(28)19-13-32-27(3)12-23(19)34-26(31)15(27)2/h5-6,17-24,29H,2,7-13H2,1,3-4H3

InChI Key

KPKHBVCOOBDWBC-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
Dicarboxylic acid or derivatives
Oxane
Cyclic alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Secondary alcohol
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	2.57	ALOGPS
logP	2.76	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	-0.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	126.95 m³·mol⁻¹	ChemAxon
Polarizability	51.41 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

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 17-hydroxy-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 (NP0207080)

MOL for NP0207080 (17-hydroxy-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 NP0207080 (17-hydroxy-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 NP0207080 (17-hydroxy-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 NP0207080 (17-hydroxy-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 NP0207080 (17-hydroxy-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 NP0207080 (17-hydroxy-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 NP0207080 (17-hydroxy-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 NP0207080 (17-hydroxy-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 NP0207080 (17-hydroxy-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 NP0207080 (17-hydroxy-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)