NP-MRD: Showing NP-Card for 5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one (NP0155607)

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Record Information

Version

1.0

Created at

2022-09-02 12:41:48 UTC

Updated at

2022-09-02 12:41:49 UTC

NP-MRD ID

NP0155607

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one

Description

5-Methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]Nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]Octadecan-3-one belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. 5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one is found in Datura inoxia. 5-Methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]Nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]Octadecan-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171513252D          

 35 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004171513252D          

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    6.4335    3.1196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3315    2.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8379    2.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  7 22  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
  3 23  1  0  0  0  0
 14 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
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 24 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 27 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0155607

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1CC(=O)C2(C)C3CCC4(C)C(CCC4C3CC3OC23C1)C1COC2(C)CC1OC(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O6/c1-15-25(31)34-22-13-27(15,3)33-14-18(22)20-7-6-19-17-11-24-29(35-24)12-16(32-5)10-23(30)28(29,4)21(17)8-9-26(19,20)2/h16-22,24H,1,6-14H2,2-5H3

> <INCHI_KEY>
DBRFBUJTEGCWJT-UHFFFAOYSA-N

> <FORMULA>
C29H40O6

> <MOLECULAR_WEIGHT>
484.633

> <EXACT_MASS>
484.282489008

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
54.374221648495066

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
3.681565035666667

> <ALOGPS_LOGS>
-6.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.786500691694656

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7074241317547245

> <JCHEM_POLAR_SURFACE_AREA>
74.36000000000001

> <JCHEM_REFRACTIVITY>
128.41769999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.53e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one

> <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      -0.888  -3.531   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.365  -2.082   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.151  -1.811   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.675  -0.363   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.191  -0.092   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.714   1.357   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.183  -1.269   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.707   0.179   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.699  -0.998   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.222   0.451   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.738   0.722   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.731  -0.456   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.403   0.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.270  -0.506   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.698  -1.985   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.424  -2.849   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.208  -1.904   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.692  -2.175   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.169  -3.624   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.653  -3.895   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.137  -4.166   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       3.660  -2.717   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.144  -2.988   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.216   0.710   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.701   0.302   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      14.039   1.064   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      14.447   2.549   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.975   2.740   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.513   1.799   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.454   2.049   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.862   3.534   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.200   4.295   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.009   5.823   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      13.685   3.887   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.631   5.103   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   22                                             
CONECT    8    7                                                            
CONECT    9    7   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   17                                             
CONECT   13   12                                                            
CONECT   14   12   15   24                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12   18                                                  
CONECT   18   17    9   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   22                                                       
CONECT   22   21    7   20   23                                             
CONECT   23   22    3                                                       
CONECT   24   14   25   30                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29   34                                             
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   24   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   27   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₀O₆

Average Mass

484.6330 Da

Monoisotopic Mass

484.28249 Da

IUPAC Name

5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one

Traditional Name

5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one

CAS Registry Number

Not Available

SMILES

COC1CC(=O)C2(C)C3CCC4(C)C(CCC4C3CC3OC23C1)C1COC2(C)CC1OC(=O)C2=C

InChI Identifier

InChI=1S/C29H40O6/c1-15-25(31)34-22-13-27(15,3)33-14-18(22)20-7-6-19-17-11-24-29(35-24)12-16(32-5)10-23(30)28(29,4)21(17)8-9-26(19,20)2/h16-22,24H,1,6-14H2,2-5H3

InChI Key

DBRFBUJTEGCWJT-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 steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Substituents

Steroid lactone
Estrane-skeleton
5,6-epoxysteroid
Delta valerolactone
Delta_valerolactone
Oxepane
Oxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
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	2.6	ALOGPS
logP	3.68	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	17.79	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	74.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	128.42 m³·mol⁻¹	ChemAxon
Polarizability	54.37 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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 5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one (NP0155607)

MOL for NP0155607 (5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D MOL for NP0155607 (5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D SDF for NP0155607 (5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D-SDF for NP0155607 (5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

PDB for NP0155607 (5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D PDB for NP0155607 (5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

SMILES for NP0155607 (5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

INCHI for NP0155607 (5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

Structure for NP0155607 (5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)

3D Structure for NP0155607 (5-methoxy-2,16-dimethyl-15-{1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl}-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecan-3-one)