NP-MRD: Showing NP-Card for (1s,5s,7s,9r,11s,12s)-5-hydroxy-2,16-dimethyl-15-[(1r,4r,5r)-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 (NP0211350)

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Record Information

Version

2.0

Created at

2022-09-05 09:36:01 UTC

Updated at

2022-09-05 09:36:01 UTC

NP-MRD ID

NP0211350

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,5s,7s,9r,11s,12s)-5-hydroxy-2,16-dimethyl-15-[(1r,4r,5r)-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

CHEMBL3138102 belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. (1s,5s,7s,9r,11s,12s)-5-hydroxy-2,16-dimethyl-15-[(1r,4r,5r)-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 metel. Based on a literature review very few articles have been published on CHEMBL3138102.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052211362D          

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M  END

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M  END


  Mrv1652309052211362D          

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 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  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
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 17 30  1  0  0  0  0
 30 31  1  1  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 13 33  1  0  0  0  0
 16 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211350

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CC[C@H]3[C@@H](C[C@H]4O[C@]44C[C@H](O)CC(=O)C34C)[C@@H]1CCC2[C@@H]1CO[C@]2(C)C[C@H]1OC(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O6/c1-14-24(31)33-21-12-26(14,3)32-13-17(21)19-6-5-18-16-10-23-28(34-23)11-15(29)9-22(30)27(28,4)20(16)7-8-25(18,19)2/h15-21,23,29H,1,5-13H2,2-4H3/t15-,16+,17+,18+,19?,20+,21-,23-,25?,26-,27?,28-/m1/s1

> <INCHI_KEY>
GBOAIYGIMWIRNM-MSSXESCYSA-N

> <FORMULA>
C28H38O6

> <MOLECULAR_WEIGHT>
470.606

> <EXACT_MASS>
470.266838944

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.191492776803784

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,5S,7S,9R,11S,12S)-5-hydroxy-2,16-dimethyl-15-[(1R,4R,5R)-1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl]-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadecan-3-one

> <JCHEM_LOGP>
3.038438532

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.156125352692598

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.953339352555588

> <JCHEM_PKA_STRONGEST_BASIC>
-2.80600505247532

> <JCHEM_POLAR_SURFACE_AREA>
85.36000000000001

> <JCHEM_REFRACTIVITY>
123.66649999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5S,7S,9R,11S,12S)-5-hydroxy-2,16-dimethyl-15-[(1R,4R,5R)-1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl]-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadecan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      14.631   9.723   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.685   8.507   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.200   8.915   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.009  10.443   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      10.862   8.154   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.454   6.669   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.388   7.418   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.447   7.169   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.975   7.360   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      14.039   5.684   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.701   4.922   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.216   5.330   0.000  0.00  0.00           C+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  C   UNK     0       8.208   2.716   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.692   2.445   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.169   0.996   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.653   0.725   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.137   0.454   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       3.660   1.903   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.144   1.632   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.151   2.809   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.365   2.538   0.000  0.00  0.00           O+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                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    2    9   10                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12   14   33                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   33                                                  
CONECT   17   16   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   21                                                       
CONECT   21   20   19   22   28                                             
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   21   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   17   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   13   16   34                                             
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₈O₆

Average Mass

470.6060 Da

Monoisotopic Mass

470.26684 Da

IUPAC Name

(1S,5S,7S,9R,11S,12S)-5-hydroxy-2,16-dimethyl-15-[(1R,4R,5R)-1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl]-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadecan-3-one

Traditional Name

(1S,5S,7S,9R,11S,12S)-5-hydroxy-2,16-dimethyl-15-[(1R,4R,5R)-1-methyl-8-methylidene-7-oxo-2,6-dioxabicyclo[3.3.1]nonan-4-yl]-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadecan-3-one

CAS Registry Number

Not Available

SMILES

CC12CC[C@H]3[C@@H](C[C@H]4O[C@]44C[C@H](O)CC(=O)C34C)[C@@H]1CCC2[C@@H]1CO[C@]2(C)C[C@H]1OC(=O)C2=C

InChI Identifier

InChI=1S/C28H38O6/c1-14-24(31)33-21-12-26(14,3)32-13-17(21)19-6-5-18-16-10-23-28(34-23)11-15(29)9-22(30)27(28,4)20(16)7-8-25(18,19)2/h15-21,23,29H,1,5-13H2,2-4H3/t15-,16+,17+,18+,19?,20+,21-,23-,25?,26-,27?,28-/m1/s1

InChI Key

GBOAIYGIMWIRNM-MSSXESCYSA-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 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
Oxepane
Delta_valerolactone
Oxane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Secondary alcohol
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Oxacycle
Ether
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
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	3.04	ChemAxon
pKa (Strongest Acidic)	14.95	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.36 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	123.67 m³·mol⁻¹	ChemAxon
Polarizability	52.19 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

31106248

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76336754

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,5s,7s,9r,11s,12s)-5-hydroxy-2,16-dimethyl-15-[(1r,4r,5r)-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 (NP0211350)

MOL for NP0211350 ((1s,5s,7s,9r,11s,12s)-5-hydroxy-2,16-dimethyl-15-[(1r,4r,5r)-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 NP0211350 ((1s,5s,7s,9r,11s,12s)-5-hydroxy-2,16-dimethyl-15-[(1r,4r,5r)-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 NP0211350 ((1s,5s,7s,9r,11s,12s)-5-hydroxy-2,16-dimethyl-15-[(1r,4r,5r)-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 NP0211350 ((1s,5s,7s,9r,11s,12s)-5-hydroxy-2,16-dimethyl-15-[(1r,4r,5r)-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 NP0211350 ((1s,5s,7s,9r,11s,12s)-5-hydroxy-2,16-dimethyl-15-[(1r,4r,5r)-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 NP0211350 ((1s,5s,7s,9r,11s,12s)-5-hydroxy-2,16-dimethyl-15-[(1r,4r,5r)-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 NP0211350 ((1s,5s,7s,9r,11s,12s)-5-hydroxy-2,16-dimethyl-15-[(1r,4r,5r)-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 NP0211350 ((1s,5s,7s,9r,11s,12s)-5-hydroxy-2,16-dimethyl-15-[(1r,4r,5r)-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 NP0211350 ((1s,5s,7s,9r,11s,12s)-5-hydroxy-2,16-dimethyl-15-[(1r,4r,5r)-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 NP0211350 ((1s,5s,7s,9r,11s,12s)-5-hydroxy-2,16-dimethyl-15-[(1r,4r,5r)-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)