NP-MRD: Showing NP-Card for 2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-one (NP0283896)

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Record Information

Version

2.0

Created at

2022-09-09 11:21:22 UTC

Updated at

2022-09-09 11:21:22 UTC

NP-MRD ID

NP0283896

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-one

Description

2,17-Dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]Nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]Nonadec-4-en-3-one belongs to the class of organic compounds known as 5,6-epoxysteroids. These are steroid derivatives sharing two carbon atoms at the 5- and 6- positions with an epoxide ring. 2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-one is found in Datura inoxia. 2,17-Dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]Nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]Nonadec-4-en-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241504382D          

 34 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004241504382D          

 34 41  0  0  0  0            999 V2000
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 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 18 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 13 33  1  0  0  0  0
 17 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0283896

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC3C(CC4OC44CC=CC(=O)C34C)C11OC1CC2C1COC2(C)CC1OC(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C28H34O6/c1-14-23(30)32-19-12-25(14,3)31-13-15(19)17-10-22-28(34-22)18-11-21-27(33-21)8-5-6-20(29)26(27,4)16(18)7-9-24(17,28)2/h5-6,15-19,21-22H,1,7-13H2,2-4H3

> <INCHI_KEY>
UWYWRVRABMRMEA-UHFFFAOYSA-N

> <FORMULA>
C28H34O6

> <MOLECULAR_WEIGHT>
466.574

> <EXACT_MASS>
466.235538815

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
50.184393599822386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-one

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
3.3453210250000005

> <ALOGPS_LOGS>
-5.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.634597094182283

> <JCHEM_PKA_STRONGEST_BASIC>
-3.727919570644375

> <JCHEM_POLAR_SURFACE_AREA>
77.66

> <JCHEM_REFRACTIVITY>
122.59039999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-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      15.975   7.360   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.447   7.169   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.513   6.419   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.454   6.669   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      10.862   8.154   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      12.200   8.915   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      12.009  10.443   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      13.685   8.507   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.631   9.723   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.701   4.922   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.039   5.684   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.270   4.114   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.698   2.635   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.424   1.771   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.997   1.190   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.137   0.454   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.675   4.257   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.191   4.528   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.714   5.977   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.183   3.351   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.707   4.799   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.699   3.622   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.222   5.071   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.738   5.342   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.731   4.164   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.403   5.550   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8   12                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8                                                            
CONECT   10    4   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    2                                                       
CONECT   13   10   14   33                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   17                                                       
CONECT   17   16   15   18   33                                             
CONECT   18   17   19   30                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   22                                                       
CONECT   22   21   20   23   28                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   22   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   18   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   13   17   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₄O₆

Average Mass

466.5740 Da

Monoisotopic Mass

466.23554 Da

IUPAC Name

2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-one

Traditional Name

2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-one

CAS Registry Number

Not Available

SMILES

CC12CCC3C(CC4OC44CC=CC(=O)C34C)C11OC1CC2C1COC2(C)CC1OC(=O)C2=C

InChI Identifier

InChI=1S/C28H34O6/c1-14-23(30)32-19-12-25(14,3)31-13-15(19)17-10-22-28(34-22)18-11-21-27(33-21)8-5-6-20(29)26(27,4)16(18)7-9-24(17,28)2/h5-6,15-19,21-22H,1,7-13H2,2-4H3

InChI Key

UWYWRVRABMRMEA-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 inoxia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5,6-epoxysteroids. These are steroid derivatives sharing two carbon atoms at the 5- and 6- positions with an epoxide ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

5,6-epoxysteroids

Direct Parent

5,6-epoxysteroids

Alternative Parents

Substituents

5,6-epoxysteroid
Naphthopyran
Naphthalene
Delta valerolactone
Delta_valerolactone
Cyclohexenone
Oxepane
Oxane
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Ketone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen 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	3.17	ALOGPS
logP	3.35	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	14.63	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	77.66 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	122.59 m³·mol⁻¹	ChemAxon
Polarizability	50.18 Å³	ChemAxon
Number of Rings	8	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 2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-one (NP0283896)

MOL for NP0283896 (2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-one)

3D MOL for NP0283896 (2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-one)

3D SDF for NP0283896 (2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-one)

3D-SDF for NP0283896 (2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-one)

PDB for NP0283896 (2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-one)

3D PDB for NP0283896 (2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-one)

SMILES for NP0283896 (2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-one)

INCHI for NP0283896 (2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-one)

Structure for NP0283896 (2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-one)

3D Structure for NP0283896 (2,17-dimethyl-16-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8,13-dioxahexacyclo[9.8.0.0²,⁷.0⁷,⁹.0¹²,¹⁴.0¹²,¹⁷]nonadec-4-en-3-one)