NP-MRD: Showing NP-Card for solassodine (NP0155848)

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Record Information

Version

2.0

Created at

2022-09-02 12:58:40 UTC

Updated at

2022-09-02 12:58:40 UTC

NP-MRD ID

NP0155848

Secondary Accession Numbers

None

Natural Product Identification

Common Name

solassodine

Description

Solasodine, also known as purapuridine or salasdine, 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. It is commercially used as a precursor for the production of complex steroidal compounds such as contraceptive pills. Solasodine is teratogenic to hamster fetuses in a dose of 1200 to 1600 mg/kg. Solasonine and solamargine are glycoalkaloid derivatives of solasodine. Solasodine is a very strong basic compound (based on its pKa). Outside of the human body, Solasodine has been detected, but not quantified in, several different foods, such as tronchuda cabbages, asian pears, corn salad, jew's ears, and angelica. This could make solasodine a potential biomarker for the consumption of these foods. Solasodine is a poisonous alkaloid chemical compound that occurs in plants of the family Solanaceae. solassodine is found in Fritillaria stenanthera, Lycianthes biflora, Solanum aculeastrum, Solanum aculeatissimum, Solanum aethiopicum, Solanum americanum, Solanum anomalum, Solanum aviculare, Solanum canense, Solanum donianum, Solanum dulcamara, Solanum laciniatum, Solanum laxum, Solanum mammosum, Solanum pinnatum and Solanum trilobatum. solassodine was first documented in 2010 (PMID: 20706906). Literature survey reveals that solasodine has diuretic, anticancer, antifungal, cardiotonic, antispermatogenetic, antiandrogenic, immunomodulatory, antipyretic and various effects on central nervous system (PMID: 21391109).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241219152D          

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M  END

     RDKit          3D

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  Mrv0541 02241219152D          

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M  END
> <DATABASE_ID>
NP0155848

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CN1

> <INCHI_IDENTIFIER>
InChI=1S/C27H43NO2/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/h5,16-17,19-24,28-29H,6-15H2,1-4H3

> <INCHI_KEY>
KWVISVAMQJWJSZ-UHFFFAOYSA-N

> <FORMULA>
C27H43NO2

> <MOLECULAR_WEIGHT>
413.6358

> <EXACT_MASS>
413.329379625

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
50.30636220135777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-ol

> <ALOGPS_LOGP>
4.45

> <JCHEM_LOGP>
4.609877547333332

> <ALOGPS_LOGS>
-5.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.204289505503816

> <JCHEM_PKA_STRONGEST_BASIC>
9.5416478856025

> <JCHEM_POLAR_SURFACE_AREA>
41.489999999999995

> <JCHEM_REFRACTIVITY>
121.94680000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.38e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
solassodine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.654  -1.699   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.654  -3.242   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.319  -4.014   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.986  -3.242   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.986  -1.699   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.319  -0.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.652  -4.014   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.319  -3.242   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.319  -1.699   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.652  -0.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.010  -0.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.010   0.605   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.319   1.372   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.652   0.605   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.469  -1.403   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.366  -0.161   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.469   1.076   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.817   0.309   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.817   1.835   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.366   2.306   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.100   0.976   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.484   1.657   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.585   3.195   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.301   4.050   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0       3.917   3.363   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0       7.968   3.880   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.010   2.149   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.016   3.808   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.986  -0.156   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -7.968  -4.050   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   29                                             
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14                                                  
CONECT   11    9   12   15                                                  
CONECT   12   11   13   17   27                                             
CONECT   13   12   14                                                       
CONECT   14   10   13                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   12   16   20                                                  
CONECT   18   16   19                                                       
CONECT   19   18   20   21   25                                             
CONECT   20   17   19   28                                                  
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   19   24                                                       
CONECT   26   23                                                            
CONECT   27   12                                                            
CONECT   28   20                                                            
CONECT   29    5                                                            
CONECT   30    2                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Value	Source
Purapuridine	HMDB
Salasdine	HMDB
Salasodine	HMDB
Solancarpidine	HMDB
Solancarpine	HMDB
Solanidine S	HMDB
Solanidine-S	HMDB
Solasod-5-en-3 beta-ol	HMDB
Solasod-5-en-3beta -ol	HMDB
Solasodin	HMDB
Solasodine hydrochloride base	HMDB
Sosasodine	HMDB
Spirosol-5-en-3-ol	HMDB
Tomatidenol	HMDB
Solasodine	MeSH
Solasodine, (3beta,22beta,25S)-isomer	MeSH
Solasodine citrate, (3alpha,22alpha,25R)-isomer	MeSH

Chemical Formula

C₂₇H₄₃NO₂

Average Mass

413.6358 Da

Monoisotopic Mass

413.32938 Da

IUPAC Name

5',7,9,13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-en-16-ol

Traditional Name

solassodine

CAS Registry Number

Not Available

SMILES

CC1C2C(CC3C4CC=C5CC(O)CCC5(C)C4CCC23C)OC11CCC(C)CN1

InChI Identifier

InChI=1S/C27H43NO2/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/h5,16-17,19-24,28-29H,6-15H2,1-4H3

InChI Key

KWVISVAMQJWJSZ-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
Fritillaria stenanthera	LOTUS Database	35616633
Lycianthes biflora	LOTUS Database	35616633
Solanum aculeastrum	LOTUS Database	35616633
Solanum aculeatissimum	LOTUS Database	35616633
Solanum aethiopicum	LOTUS Database	35616633
Solanum americanum	LOTUS Database	35616633
Solanum anomalum	LOTUS Database	35616633
Solanum aviculare	LOTUS Database	35616633
Solanum canense	LOTUS Database	35616633
Solanum donianum	LOTUS Database	35616633
Solanum dulcamara	LOTUS Database	35616633
Solanum laciniatum	LOTUS Database	35616633
Solanum laxum	LOTUS Database	35616633
Solanum mammosum	LOTUS Database	35616633
Solanum pinnatum	LOTUS Database	35616633
Solanum trilobatum	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-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
Azasteroid
Delta-5-steroid
Azaspirodecane
Alkaloid or derivatives
Piperidine
Cyclic alcohol
Tetrahydrofuran
Hemiaminal
Secondary alcohol
Oxacycle
Azacycle
Secondary aliphatic amine
Organoheterocyclic compound
Secondary amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Alcohol
Amine
Organonitrogen compound
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	4.45	ALOGPS
logP	4.61	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	41.49 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	121.95 m³·mol⁻¹	ChemAxon
Polarizability	50.31 Å³	ChemAxon
Number of Rings	6	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

HMDB0035282

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Solasodine

METLIN ID

Not Available

PubChem Compound

5250

PDB ID

Not Available

ChEBI ID

565242

Good Scents ID

Not Available

References

General References

Pandurangan A, Khosa RL, Hemalatha S: Antinociceptive activity of steroid alkaloids isolated from Solanum trilobatum Linn. J Asian Nat Prod Res. 2010 Aug;12(8):691-5. doi: 10.1080/10286020.2010.497997. [PubMed:20706906 ]
Pandurangan A, Khosa RL, Hemalatha S: Anti-inflammatory activity of an alkaloid from Solanum trilobatum on acute and chronic inflammation models. Nat Prod Res. 2011 Jul;25(12):1132-41. doi: 10.1080/14786410903370783. [PubMed:21391109 ]
LOTUS database [Link]

Showing NP-Card for solassodine (NP0155848)

MOL for NP0155848 (solassodine)

3D MOL for NP0155848 (solassodine)

3D SDF for NP0155848 (solassodine)

3D-SDF for NP0155848 (solassodine)

PDB for NP0155848 (solassodine)

3D PDB for NP0155848 (solassodine)

SMILES for NP0155848 (solassodine)

INCHI for NP0155848 (solassodine)

Structure for NP0155848 (solassodine)

3D Structure for NP0155848 (solassodine)