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Showing NP-Card for 22-Isopimpifolidine (NP0049718)

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Record Information
Version1.0
Created at2022-03-17 21:16:59 UTC
Updated at2022-03-17 21:16:59 UTC
NP-MRD IDNP0049718
Secondary Accession NumbersNone
Natural Product Identification
Common Name22-Isopimpifolidine
DescriptionSolanocardinol is also known as pimpifolidine. Solanocardinol is a very strong basic compound (based on its pKa). Outside of the human body, solanocardinol has been detected, but not quantified in, garden tomato. 22-Isopimpifolidine is found in Solanum thomasiifolium. It was first documented in 2000 (PMID: 11413487). This could make solanocardinol a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049718 (22-Isopimpifolidine)


  Mrv0541 02241209112D          

 31 36  0  0  0  0            999 V2000
    3.0395    2.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2185    2.1183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830    1.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0622    1.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7266    0.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0570    0.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7721    0.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857    0.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857   -0.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2007   -0.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9157   -0.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6294   -0.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6294   -1.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9157   -2.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2007   -1.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857   -2.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7721   -1.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7721   -0.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0570   -0.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7266   -0.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2121   -0.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.0570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3685    0.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1893    0.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5248    1.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3444    1.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5781    1.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295    1.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2007   -0.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8539    0.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3444   -2.2048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 23  1  0  0  0  0
  4  5  1  0  0  0  0
  4 27  1  0  0  0  0
  5  6  1  0  0  0  0
  5 21  1  0  0  0  0
  6  7  1  0  0  0  0
  6 19  1  0  0  0  0
  6 28  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 18  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 10 29  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 31  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
 17 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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 30  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
Download

3D MOL for NP0049718 (22-Isopimpifolidine)

Download
3D SDF for NP0049718 (22-Isopimpifolidine)

  Mrv0541 02241209112D          

 31 36  0  0  0  0            999 V2000
    3.0395    2.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2185    2.1183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8830    1.3647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0622    1.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7266    0.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0570    0.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7721    0.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857    0.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857   -0.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2007   -0.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9157   -0.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6294   -0.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6294   -1.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9157   -2.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2007   -1.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857   -2.2048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7721   -1.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7721   -0.9673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0570   -0.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7266   -0.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2121   -0.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.0570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3685    0.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1893    0.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5248    1.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3444    1.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5781    1.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0295    1.0897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2007   -0.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8539    0.0295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3444   -2.2048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 25  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 23  1  0  0  0  0
  4  5  1  0  0  0  0
  4 27  1  0  0  0  0
  5  6  1  0  0  0  0
  5 21  1  0  0  0  0
  6  7  1  0  0  0  0
  6 19  1  0  0  0  0
  6 28  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 18  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 10 29  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 31  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
 17 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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 30  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049718

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CNC2C(C)C3C(CC4C5CCC6CC(O)CCC6(C)C5CCC34C)OC2(O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C27H45NO3/c1-15-13-27(30)24(28-14-15)16(2)23-22(31-27)12-21-19-6-5-17-11-18(29)7-9-25(17,3)20(19)8-10-26(21,23)4/h15-24,28-30H,5-14H2,1-4H3

> <INCHI_KEY>
ZHFCFFSSVSIEIR-UHFFFAOYSA-N

> <FORMULA>
C27H45NO3

> <MOLECULAR_WEIGHT>
431.6511

> <EXACT_MASS>
431.339944311

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
52.499769750962095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10,14,16,20-tetramethyl-23-oxa-18-azahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁴.0¹⁷,²²]pentacosane-7,22-diol

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
4.054904154666666

> <ALOGPS_LOGS>
-4.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.2963963211217

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.560923592194722

> <JCHEM_PKA_STRONGEST_BASIC>
9.442385388660279

> <JCHEM_POLAR_SURFACE_AREA>
61.72

> <JCHEM_REFRACTIVITY>
122.4031

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.17e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10,14,16,20-tetramethyl-23-oxa-18-azahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁴.0¹⁷,²²]pentacosane-7,22-diol

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0049718 (22-Isopimpifolidine)
Download
PDB for NP0049718 (22-Isopimpifolidine)
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       5.674   4.116   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       4.141   3.954   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       3.515   2.547   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.983   2.386   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.356   0.979   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.106   0.504   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.441   1.274   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.773   0.504   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.773  -1.036   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.108  -1.806   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.443  -1.036   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.775  -1.806   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.775  -3.346   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.443  -4.116   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.108  -3.346   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.773  -4.116   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.441  -3.346   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.441  -1.806   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.106  -1.036   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.356  -1.513   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.263  -0.266   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.795  -0.106   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       4.421   1.303   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.953   1.462   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.580   2.868   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.110   3.030   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.079   3.633   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.055   2.034   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.108  -0.266   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.327   0.055   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -8.110  -4.116   0.000  0.00  0.00           O+0
CONECT    1    2   25                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5   27                                                  
CONECT    5    4    6   21                                                  
CONECT    6    5    7   19   28                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11   15   29                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   31                                                  
CONECT   14   13   15                                                       
CONECT   15   10   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18    9   17   19                                                  
CONECT   19    6   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21    5   20   22                                                  
CONECT   22   21   23                                                       
CONECT   23    3   22   24   30                                             
CONECT   24   23   25                                                       
CONECT   25    1   24   26                                                  
CONECT   26   25                                                            
CONECT   27    4                                                            
CONECT   28    6                                                            
CONECT   29   10                                                            
CONECT   30   23                                                            
CONECT   31   13                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

Download
3D PDB for NP0049718 (22-Isopimpifolidine)
Download
SMILES for NP0049718 (22-Isopimpifolidine)
CC1CNC2C(C)C3C(CC4C5CCC6CC(O)CCC6(C)C5CCC34C)OC2(O)C1
Download
INCHI for NP0049718 (22-Isopimpifolidine)
InChI=1S/C27H45NO3/c1-15-13-27(30)24(28-14-15)16(2)23-22(31-27)12-21-19-6-5-17-11-18(29)7-9-25(17,3)20(19)8-10-26(21,23)4/h15-24,28-30H,5-14H2,1-4H3
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View in JSmol
Synonyms
ValueSource
PimpifolidineHMDB
Chemical FormulaC27H45NO3
Average Mass431.6511 Da
Monoisotopic Mass431.33994 Da
IUPAC Name10,14,16,20-tetramethyl-23-oxa-18-azahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁴.0¹⁷,²²]pentacosane-7,22-diol
Traditional Name10,14,16,20-tetramethyl-23-oxa-18-azahexacyclo[12.11.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁴.0¹⁷,²²]pentacosane-7,22-diol
CAS Registry Number138665-46-0
SMILES
CC1CNC2C(C)C3C(CC4C5CCC6CC(O)CCC6(C)C5CCC34C)OC2(O)C1
InChI Identifier
InChI=1S/C27H45NO3/c1-15-13-27(30)24(28-14-15)16(2)23-22(31-27)12-21-19-6-5-17-11-18(29)7-9-25(17,3)20(19)8-10-26(21,23)4/h15-24,28-30H,5-14H2,1-4H3
InChI KeyZHFCFFSSVSIEIR-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Solanum lycopersicumFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Solanum thomasiifoliumLOTUS Database
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as solanocapsine-type alkaloids. These are steroidal alkaloids with a structure that is characterized by a docosahydronaphth[2,1:4',5']Indene ring system fused to a pyrano[3,2-b]pyridine moiety.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassSteroids and steroid derivatives  
Sub ClassSteroidal alkaloids  
Direct ParentSolanocapsine-type alkaloids  
Alternative Parents
Substituents
  • Solanocapsine skeleton
    • 

  • 23-hydroxysteroid
    • 

  • 3-hydroxysteroid
    • 

  • Hydroxysteroid
    • 

  • Azasteroid
    • 

  • Alkaloid or derivatives
    • 

  • Oxane
    • 

  • Piperidine
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Hemiacetal
    • 

  • Oxacycle
    • 

  • Secondary amine
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Secondary aliphatic amine
    • 

  • Alcohol
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Organic oxygen compound
    • 

  • Amine
    • 

  • Organic nitrogen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.6ALOGPS
logP4.05ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)11.56ChemAxon
pKa (Strongest Basic)9.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.72 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity122.4 m³·mol⁻¹ChemAxon
Polarizability52.5 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038836  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020574  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73802037  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487  ] 
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246  ] 
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880  ] 
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567  ]