NP-MRD: Showing NP-Card for (1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-17-en-16-one (NP0315001)

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Record Information

Version

2.0

Created at

2022-09-11 13:24:53 UTC

Updated at

2022-09-11 13:24:53 UTC

NP-MRD ID

NP0315001

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-17-en-16-one

Description

SOLASODENONE belongs to the class of organic compounds known as spirosolanes and derivatives. These are steroidal alkaloids with a structure containing a spirosolane skeleton. Siporosolane is a polycyclic compound that is characterized by a 1-oxa-6-azaspiro[4.5]Decane moiety where the oxolane ring is fused to a docosahydronaphth[2,1:4',5']Indene ring system. Spirosolane arises from the conversion of a cholestane side-chain into a bicyclic system containing a piperidine and a tetrahydrofuran ring. (1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-17-en-16-one is found in Solanum aviculare and Solanum procumbens. (1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-17-en-16-one was first documented in 2015 (PMID: 25510927). Based on a literature review very few articles have been published on SOLASODENONE.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112215242D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309112215242D          

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M  END
> <DATABASE_ID>
NP0315001

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CCC5=CC(=O)CC[C@]5(C)[C@H]4CC[C@]23C)O[C@]11CC[C@@H](C)CN1

> <INCHI_IDENTIFIER>
InChI=1S/C27H41NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h13,16-17,20-24,28H,5-12,14-15H2,1-4H3/t16-,17+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1

> <INCHI_KEY>
XCAKPWXDUSEAEH-CLGLNXEMSA-N

> <FORMULA>
C27H41NO2

> <MOLECULAR_WEIGHT>
411.63

> <EXACT_MASS>
411.313729564

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
50.33787262204019

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-piperidin]-17-en-16-one

> <JCHEM_LOGP>
5.177123495333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.08674910182926

> <JCHEM_PKA_STRONGEST_BASIC>
9.541647885943389

> <JCHEM_POLAR_SURFACE_AREA>
38.33

> <JCHEM_REFRACTIVITY>
120.89539999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-piperidin]-17-en-16-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      13.454  -7.989   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.686  -6.467   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.054  -5.760   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.805  -4.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.173  -3.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.268  -4.616   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.805  -4.526   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.497  -3.150   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.034  -3.061   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.880  -4.347   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.418  -4.258   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.264  -5.545   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      25.801  -5.455   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      23.573  -6.921   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.035  -7.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.189  -5.724   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.498  -7.100   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.652  -5.813   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.960  -7.189   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.423  -7.279   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.577  -5.992   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.746  -7.289   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.282  -4.008   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.591  -5.384   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.048  -6.825   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.528  -7.075   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.552  -5.884   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.032  -6.134   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.095  -4.443   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0      11.615  -4.193   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   10   17   18                                             
CONECT   17   16                                                            
CONECT   18   16    7   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    6    3   22                                             
CONECT   22   21                                                            
CONECT   23    4   24                                                       
CONECT   24   23    2   25   30                                             
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   24                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₁NO₂

Average Mass

411.6300 Da

Monoisotopic Mass

411.31373 Da

IUPAC Name

(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-piperidin]-17-en-16-one

Traditional Name

(1S,2S,4S,5'R,6R,7S,8R,9S,12S,13R)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-piperidin]-17-en-16-one

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CCC5=CC(=O)CC[C@]5(C)[C@H]4CC[C@]23C)O[C@]11CC[C@@H](C)CN1

InChI Identifier

InChI=1S/C27H41NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h13,16-17,20-24,28H,5-12,14-15H2,1-4H3/t16-,17+,20-,21+,22+,23+,24+,25+,26+,27-/m1/s1

InChI Key

XCAKPWXDUSEAEH-CLGLNXEMSA-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
Solanum aviculare	LOTUS Database	35616633
Solanum procumbens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as spirosolanes and derivatives. These are steroidal alkaloids with a structure containing a spirosolane skeleton. Siporosolane is a polycyclic compound that is characterized by a 1-oxa-6-azaspiro[4.5]Decane moiety where the oxolane ring is fused to a docosahydronaphth[2,1:4',5']Indene ring system. Spirosolane arises from the conversion of a cholestane side-chain into a bicyclic system containing a piperidine and a tetrahydrofuran ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal alkaloids

Direct Parent

Spirosolanes and derivatives

Alternative Parents

Substituents

Spirosolane skeleton
3-oxo-delta-4-steroid
3-oxosteroid
Oxosteroid
Azasteroid
Delta-4-steroid
Azaspirodecane
Alkaloid or derivatives
Cyclohexenone
Piperidine
Oxolane
Cyclic ketone
Hemiaminal
Ketone
Organoheterocyclic compound
Azacycle
Secondary amine
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Amine
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	5.18	ChemAxon
pKa (Strongest Acidic)	19.09	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.33 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	120.9 m³·mol⁻¹	ChemAxon
Polarizability	50.34 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	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

293968

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

331777

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tata A, Perez CJ, Hamid TS, Bayfield MA, Ifa DR: Analysis of metabolic changes in plant pathosystems by imprint imaging DESI-MS. J Am Soc Mass Spectrom. 2015 Apr;26(4):641-8. doi: 10.1007/s13361-014-1039-0. Epub 2014 Dec 16. [PubMed:25510927 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-17-en-16-one (NP0315001)

MOL for NP0315001 ((1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-17-en-16-one)

3D MOL for NP0315001 ((1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-17-en-16-one)

3D SDF for NP0315001 ((1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-17-en-16-one)

3D-SDF for NP0315001 ((1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-17-en-16-one)

PDB for NP0315001 ((1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-17-en-16-one)

3D PDB for NP0315001 ((1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-17-en-16-one)

SMILES for NP0315001 ((1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-17-en-16-one)

INCHI for NP0315001 ((1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-17-en-16-one)

Structure for NP0315001 ((1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-17-en-16-one)

3D Structure for NP0315001 ((1s,2s,4s,5'r,6r,7s,8r,9s,12s,13r)-5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-17-en-16-one)