NP-MRD: Showing NP-Card for Heliotrine (NP0051164)

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Record Information

Version

2.0

Created at

2022-04-27 22:34:19 UTC

Updated at

2022-04-27 22:34:19 UTC

NP-MRD ID

NP0051164

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Heliotrine

Description

HELIOTRINE belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Heliotrine is found in Arnebia decumbens, Heliotorpium digynum, Heliotropium acutiflorum, Heliotropium arbainense, Heliotropium bacciferum , Heliotropium circinatum, Heliotropium curassavicum, Heliotropium dasycarpum, Heliotropium dissitiflorum, Heliotropium eichwaldii, Heliotropium europaeum , Heliotropium hirsutissimum, Heliotropium indicum , Heliotropium lasiocarpum, Heliotropium olgae, Heliotropium rotundifolium, Heliotropium suaveolens, Heliotropium subulatum, Heliotropium supinum, Heliotropium transoxanum, Moltkiopsis ciliata and Symphytum caucasium. Heliotrine was first documented in 2021 (PMID: 34185104). Based on a literature review a small amount of articles have been published on HELIOTRINE (PMID: 34158818) (PMID: 35285352) (PMID: 34945435) (PMID: 33780325).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 49 50  0  0  0  0  0  0  0  0999 V2000
   -3.5791   -2.8675   -1.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7888   -1.7466   -0.2321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5679   -1.1824    0.1070 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3219   -1.2617    1.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4257    0.2018   -0.4826 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5304   -0.0052   -1.8859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0670    0.7440   -0.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6267    1.0618    0.8894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1513    0.9540   -1.3152 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1397    1.4576   -1.1136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9020    0.4540   -0.2918 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5128   -0.7089    0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6479   -1.3375    0.9484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4902   -0.1680    1.2585 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8857   -0.5520    1.3029 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5256   -0.0091    0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2955    0.0705   -0.8733 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5233    0.9021   -1.9586 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3051    0.6643    0.1131 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5247    1.1410   -0.1420 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7497    1.4374    1.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1941    2.4691   -0.8376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0405   -2.6414   -1.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5756   -3.2724   -1.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9745   -3.5772   -0.4300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7755   -1.8179   -0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6249   -2.1063    1.8545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2939   -1.5763    2.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0307   -0.3465    2.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0803    0.7726   -2.2991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6618    1.5080   -2.0904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1559    2.4610   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5534   -1.1788    0.0622 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1991   -1.7547    1.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1964   -2.0707    0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3965   -0.2059    2.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9373   -1.6723    1.2208 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8542    1.0370    0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3083   -0.6436   -0.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0405   -0.9565   -1.1332 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2538    0.5314   -2.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5536    1.7287    0.2845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4729    0.8047   -0.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2050    0.6355    1.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5054    2.2797    1.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8517    1.8813    1.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2745    2.3850   -1.9286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1888    2.8243   -0.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9170    3.2526   -0.5159 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  6
  5 20  1  0
 20 21  1  0
 20 22  1  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 11  1  0
 19 14  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  6
  4 27  1  0
  4 28  1  0
  4 29  1  0
  6 30  1  0
 20 43  1  6
 21 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  6
 18 41  1  0
 19 42  1  1
M  END


  Mrv1652304282200342D          

 22 23  0  0  1  0            999 V2000
    0.7846   -1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4849   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0619   -2.2910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3168   -3.0756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7648   -3.6887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1238   -3.2472    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9308   -3.4187    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4828   -2.8056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1857   -4.2033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9927   -4.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9523   -4.0541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2953   -2.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0800   -2.1853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6823   -1.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  8  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 15  1  6  0  0  0
 10 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  1 21  1  0  0  0  0
 21 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051164

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H](C)[C@@](O)(C(C)C)C(=O)OCC1=CCN2CC[C@H](O)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C16H27NO5/c1-10(2)16(20,11(3)21-4)15(19)22-9-12-5-7-17-8-6-13(18)14(12)17/h5,10-11,13-14,18,20H,6-9H2,1-4H3/t11-,13+,14-,16+/m1/s1

> <INCHI_KEY>
LMFKRLGHEKVMNT-UJDVCPFMSA-N

> <FORMULA>
C16H27NO5

> <MOLECULAR_WEIGHT>
313.394

> <EXACT_MASS>
313.188922973

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
33.616656094602014

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(1S,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoate

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
0.3520115099999998

> <ALOGPS_LOGS>
-1.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.483177674299721

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.334457978746942

> <JCHEM_PKA_STRONGEST_BASIC>
7.816509679486545

> <JCHEM_POLAR_SURFACE_AREA>
79.23

> <JCHEM_REFRACTIVITY>
82.69369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
heliotron

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.465  -0.476   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.905  -1.246   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000  -2.492   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.476  -3.956   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.982  -4.277   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.458  -5.741   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.428  -6.886   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.964  -6.061   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.471  -6.382   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.501  -5.237   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.947  -7.846   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -7.453  -8.166   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.644  -7.568   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.285  -4.555   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.749  -4.079   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.140  -3.525   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.405  -3.956   0.000  0.00  0.00           O+0
CONECT    1    2    5   21                                                  
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15   16                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   10                                                            
CONECT   16   10   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    2   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    1   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
9-Heliotrylheliotridine	Kegg

Chemical Formula

C₁₆H₂₇NO₅

Average Mass

313.3940 Da

Monoisotopic Mass

313.18892 Da

IUPAC Name

[(1S,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S)-2-hydroxy-2-[(1R)-1-methoxyethyl]-3-methylbutanoate

Traditional Name

heliotron

CAS Registry Number

Not Available

SMILES

CO[C@H](C)[C@@](O)(C(C)C)C(=O)OCC1=CCN2CC[C@H](O)[C@@H]12

InChI Identifier

InChI=1S/C16H27NO5/c1-10(2)16(20,11(3)21-4)15(19)22-9-12-5-7-17-8-6-13(18)14(12)17/h5,10-11,13-14,18,20H,6-9H2,1-4H3/t11-,13+,14-,16+/m1/s1

InChI Key

LMFKRLGHEKVMNT-UJDVCPFMSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Arnebia decumbens	Plant	KNApSAcK
Heliotorpium digynum	-	KNApSAcK
Heliotropium acutiflorum	Plant	KNApSAcK
Heliotropium arbainense	Plant	KNApSAcK
Heliotropium bacciferum	Plant	KNApSAcK
Heliotropium circinatum	Plant	KNApSAcK
Heliotropium curassavicum	Plant	KNApSAcK
Heliotropium dasycarpum	Plant	KNApSAcK
Heliotropium dissitiflorum	Plant	KNApSAcK
Heliotropium eichwaldii	Plant	KNApSAcK
Heliotropium europaeum	Plant	KNApSAcK
Heliotropium hirsutissimum	Plant	KNApSAcK
Heliotropium indicum	Plant	KNApSAcK
Heliotropium lasiocarpum	LOTUS Database	35616633
Heliotropium olgae	Plant	KNApSAcK
Heliotropium rotundifolium	Plant	KNApSAcK
Heliotropium suaveolens	LOTUS Database	35616633
Heliotropium subulatum	LOTUS Database	35616633
Heliotropium supinum	Plant	KNApSAcK
Heliotropium transoxanum	Plant	KNApSAcK
Moltkiopsis ciliata	LOTUS Database	35616633
Symphytum caucasium	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Not Available

Sub Class

Not Available

Direct Parent

Alkaloids and derivatives

Alternative Parents

Substituents

Alkaloid or derivatives
Pyrrolizine
Fatty acid ester
N-alkylpyrrolidine
Fatty acyl
Pyrrolidine
Pyrroline
Tertiary alcohol
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Azacycle
Ether
Monocarboxylic acid or derivatives
Amine
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

pyrrolizines (CHEBI:5643 )
Pyrrolizidine alkaloids (C10324 )

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	0.99	ALOGPS
logP	0.35	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	11.33	ChemAxon
pKa (Strongest Basic)	7.82	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.23 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	82.69 m³·mol⁻¹	ChemAxon
Polarizability	33.62 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00002090

Chemspider ID

792587

KEGG Compound ID

C10324

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

906426

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

rw1079971

References

General References

Buchmueller J, Sprenger H, Ebmeyer J, Rasinger JD, Creutzenberg O, Schaudien D, Hengstler JG, Guenther G, Braeuning A, Hessel-Pras S: Pyrrolizidine alkaloid-induced transcriptomic changes in rat lungs in a 28-day subacute feeding study. Arch Toxicol. 2021 Aug;95(8):2785-2796. doi: 10.1007/s00204-021-03108-x. Epub 2021 Jun 29. [PubMed:34185104 ]
Sarkar C, Mondal M, Khanom B, Hossain MM, Hossain MS, Sureda A, Islam MT, Martorell M, Kumar M, Sharifi-Rad J, Al-Harrasi A, Al-Rawahi A: Heliotropium indicum L.: From Farm to a Source of Bioactive Compounds with Therapeutic Activity. Evid Based Complement Alternat Med. 2021 Jun 1;2021:9965481. doi: 10.1155/2021/9965481. eCollection 2021. [PubMed:34158818 ]
Nardin T, Larcher R, Barnaba C, Bertoldi D, Pasut D, Romanzin A, Piasentier E: Alkaloid profiling of Italian alpine herbs using high resolution mass spectrometry (Orbitrap-MS). Nat Prod Res. 2022 Mar 12:1-8. doi: 10.1080/14786419.2022.2050908. [PubMed:35285352 ]
Senturk H, Eksin E, Zeybek U, Erdem A: Detection of Senecionine in Dietary Sources by Single-Use Electrochemical Sensor. Micromachines (Basel). 2021 Dec 20;12(12). pii: mi12121585. doi: 10.3390/mi12121585. [PubMed:34945435 ]
Picron JF, Philippe F, Dubrulle N, Van Hoeck E, Giraud N, Goscinny S, Vanhee C: Targeted LC-MS/MS combined with multilocus DNA metabarcoding as a combinatory approach to determine the amount and the source of pyrrolizidine alkaloids contamination in popular cooking herbs, seeds, spices and leafy vegetables. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2021 Jun;38(6):962-977. doi: 10.1080/19440049.2021.1889043. Epub 2021 Mar 29. [PubMed:33780325 ]

Showing NP-Card for Heliotrine (NP0051164)

MOL for NP0051164 (Heliotrine)

3D MOL for NP0051164 (Heliotrine)

3D SDF for NP0051164 (Heliotrine)

3D-SDF for NP0051164 (Heliotrine)

PDB for NP0051164 (Heliotrine)

3D PDB for NP0051164 (Heliotrine)

SMILES for NP0051164 (Heliotrine)

INCHI for NP0051164 (Heliotrine)

Structure for NP0051164 (Heliotrine)

3D Structure for NP0051164 (Heliotrine)