NP-MRD: Showing NP-Card for (1r,2s,4s,5'r,6r,7s,8r,9s,10r,12s,13r,16s)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid (NP0195539)

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Record Information

Version

2.0

Created at

2022-09-04 13:25:24 UTC

Updated at

2022-09-04 13:25:24 UTC

NP-MRD ID

NP0195539

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4s,5'r,6r,7s,8r,9s,10r,12s,13r,16s)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid

Description

(1R,2S,4S,5'R,6R,7S,8R,9S,10R,12S,13R,16S)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid 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. (1r,2s,4s,5'r,6r,7s,8r,9s,10r,12s,13r,16s)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid is found in Solanum nigrum. Based on a literature review very few articles have been published on (1R,2S,4S,5'R,6R,7S,8R,9S,10R,12S,13R,16S)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]Icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309042215252D          

 33 38  0  0  1  0            999 V2000
    7.2076   -4.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319   -3.4645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0648   -3.0857    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9311   -2.2716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6640   -1.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2507   -2.4728    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0743   -2.4249    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4446   -1.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2682   -1.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7215   -2.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5451   -2.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9984   -2.9704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.8221   -2.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6282   -3.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8046   -3.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3512   -3.0662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9810   -3.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5276   -3.1142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1573   -3.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3337   -3.8994    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9635   -4.6366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8804   -3.2101    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4351   -3.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1155   -2.1473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7452   -2.8845    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4540   -3.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6399   -3.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1170   -3.1521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3030   -3.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0118   -4.0577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7801   -2.6477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4082   -2.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2223   -2.2464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
  6 22  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  1  0  0  0
  4 24  1  1  0  0  0
 25 24  1  1  0  0  0
  2 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
 28 29  1  1  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 28 32  1  0  0  0  0
 32 33  1  0  0  0  0
 25 33  1  0  0  0  0
M  END


  Mrv1652309042215252D          

 33 38  0  0  1  0            999 V2000
    7.2076   -4.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3319   -3.4645    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0648   -3.0857    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9311   -2.2716    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.6640   -1.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2507   -2.4728    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0743   -2.4249    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.4446   -1.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2682   -1.6397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7215   -2.3290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5451   -2.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9984   -2.9704    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.8221   -2.9224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6282   -3.7076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8046   -3.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3512   -3.0662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9810   -3.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5276   -3.1142    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1573   -3.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3337   -3.8994    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.9635   -4.6366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8804   -3.2101    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.4351   -3.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1155   -2.1473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7452   -2.8845    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4540   -3.6564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6399   -3.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1170   -3.1521    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3030   -3.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0118   -4.0577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7801   -2.6477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4082   -2.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2223   -2.2464    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 20 22  1  0  0  0  0
  6 22  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  1  0  0  0
  4 24  1  1  0  0  0
 25 24  1  1  0  0  0
  2 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
 28 29  1  1  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 28 32  1  0  0  0  0
 32 33  1  0  0  0  0
 25 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195539

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4C[C@@H](O)[C@]23C)O[C@]11CC[C@H](CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H41NO5/c1-14-23-21(33-27(14)9-6-15(13-28-27)24(31)32)11-20-18-5-4-16-10-17(29)7-8-25(16,2)19(18)12-22(30)26(20,23)3/h4,14-15,17-23,28-30H,5-13H2,1-3H3,(H,31,32)/t14-,15+,17-,18+,19-,20-,21-,22+,23-,25-,26+,27+/m0/s1

> <INCHI_KEY>
GPTPCRUWEMJUEE-JHRURKGISA-N

> <FORMULA>
C27H41NO5

> <MOLECULAR_WEIGHT>
459.627

> <EXACT_MASS>
459.298473424

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.200061383510146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,4S,5'R,6R,7S,8R,9S,10R,12S,13R,16S)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid

> <JCHEM_LOGP>
-0.07930333866403312

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.678310168490825

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3878347134198763

> <JCHEM_PKA_STRONGEST_BASIC>
9.38141062678635

> <JCHEM_POLAR_SURFACE_AREA>
99.02

> <JCHEM_REFRACTIVITY>
125.07659999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4S,5'R,6R,7S,8R,9S,10R,12S,13R,16S)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-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  O   UNK     0      16.732  -8.655   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      16.577  -5.992   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.746  -7.289   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.282  -4.008   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.591  -5.384   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.048  -6.825   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.528  -7.075   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.552  -5.884   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.032  -6.134   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.489  -7.574   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       7.056  -4.942   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.095  -4.443   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0      11.615  -4.193   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4   22                                                  
CONECT    4    3    5   24                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   22                                                  
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   22                                                  
CONECT   21   20                                                            
CONECT   22   20    6    3   23                                             
CONECT   23   22                                                            
CONECT   24    4   25                                                       
CONECT   25   24    2   26   33                                             
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   28   33                                                       
CONECT   33   32   25                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,4S,5'r,6R,7S,8R,9S,10R,12S,13R,16S)-10,16-Dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0,.0,.0,]icosane-6,2'-piperidin]-18-ene-5'-carboxylate	Generator

Chemical Formula

C₂₇H₄₁NO₅

Average Mass

459.6270 Da

Monoisotopic Mass

459.29847 Da

IUPAC Name

(1R,2S,4S,5'R,6R,7S,8R,9S,10R,12S,13R,16S)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid

Traditional Name

(1R,2S,4S,5'R,6R,7S,8R,9S,10R,12S,13R,16S)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC=C5C[C@@H](O)CC[C@]5(C)[C@H]4C[C@@H](O)[C@]23C)O[C@]11CC[C@H](CN1)C(O)=O

InChI Identifier

InChI=1S/C27H41NO5/c1-14-23-21(33-27(14)9-6-15(13-28-27)24(31)32)11-20-18-5-4-16-10-17(29)7-8-25(16,2)19(18)12-22(30)26(20,23)3/h4,14-15,17-23,28-30H,5-13H2,1-3H3,(H,31,32)/t14-,15+,17-,18+,19-,20-,21-,22+,23-,25-,26+,27+/m0/s1

InChI Key

GPTPCRUWEMJUEE-JHRURKGISA-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 nigrum	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
Prostaglandin skeleton
Eicosanoid
3-hydroxy-delta-5-steroid
3-hydroxysteroid
Hydroxysteroid
12-hydroxysteroid
3-beta-hydroxy-delta-5-steroid
3-beta-hydroxysteroid
Azasteroid
Delta-5-steroid
Azaspirodecane
Piperidinecarboxylic acid
Alkaloid or derivatives
Piperidine
Fatty acyl
Cyclic alcohol
Tetrahydrofuran
Amino acid or derivatives
Hemiaminal
Secondary alcohol
Amino acid
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Azacycle
Secondary aliphatic amine
Organoheterocyclic compound
Secondary amine
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Alcohol
Amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen 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	-0.079	ChemAxon
pKa (Strongest Acidic)	3.39	ChemAxon
pKa (Strongest Basic)	9.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.02 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	125.08 m³·mol⁻¹	ChemAxon
Polarizability	53.2 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10181214

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21573758

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,4s,5'r,6r,7s,8r,9s,10r,12s,13r,16s)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid (NP0195539)

MOL for NP0195539 ((1r,2s,4s,5'r,6r,7s,8r,9s,10r,12s,13r,16s)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid)

3D MOL for NP0195539 ((1r,2s,4s,5'r,6r,7s,8r,9s,10r,12s,13r,16s)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid)

3D SDF for NP0195539 ((1r,2s,4s,5'r,6r,7s,8r,9s,10r,12s,13r,16s)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid)

3D-SDF for NP0195539 ((1r,2s,4s,5'r,6r,7s,8r,9s,10r,12s,13r,16s)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid)

PDB for NP0195539 ((1r,2s,4s,5'r,6r,7s,8r,9s,10r,12s,13r,16s)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid)

3D PDB for NP0195539 ((1r,2s,4s,5'r,6r,7s,8r,9s,10r,12s,13r,16s)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid)

SMILES for NP0195539 ((1r,2s,4s,5'r,6r,7s,8r,9s,10r,12s,13r,16s)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid)

INCHI for NP0195539 ((1r,2s,4s,5'r,6r,7s,8r,9s,10r,12s,13r,16s)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid)

Structure for NP0195539 ((1r,2s,4s,5'r,6r,7s,8r,9s,10r,12s,13r,16s)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid)

3D Structure for NP0195539 ((1r,2s,4s,5'r,6r,7s,8r,9s,10r,12s,13r,16s)-10,16-dihydroxy-7,9,13-trimethyl-5-oxaspiro[pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane-6,2'-piperidin]-18-ene-5'-carboxylic acid)