NP-MRD: Showing NP-Card for histrionicotoxin (NP0180805)

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Record Information

Version

2.0

Created at

2022-09-03 19:13:07 UTC

Updated at

2022-09-03 19:13:07 UTC

NP-MRD ID

NP0180805

Secondary Accession Numbers

None

Natural Product Identification

Common Name

histrionicotoxin

Description

Histrionicotoxin belongs to the class of organic compounds known as histrionicotoxins. These are frog toxins structurally characterized by the presence of a dodecahydropyrrolo[1,2-a]quinolin-1-yl}ethanol moiety or a 2,7-disubstituted 1-azaspiro[5.5]Undecan-8-ol moiety. Histrionicotoxin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. histrionicotoxin is found in Mantella madagascariensis. histrionicotoxin was first documented in 2018 (PMID: 35542821). Based on a literature review a small amount of articles have been published on histrionicotoxin (PMID: 35201668) (PMID: 33973732) (PMID: 32835524) (PMID: 32452606).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 46 47  0  0  0  0  0  0  0  0999 V2000
    6.8675    2.0004    0.8423 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8958    1.6942    0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7506    1.3100   -0.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5230    1.7419   -0.3050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3486    1.3200   -1.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3664    0.5985   -0.2412 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9783   -0.6228    0.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9349   -1.2539    1.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4264   -0.6302    1.0974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375   -0.5800   -0.3774 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7170   -2.0023   -0.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6488   -2.8976   -0.1194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9989   -2.2659    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1728   -1.0323   -0.8139 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3614   -1.4191   -2.1557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1040   -0.0076   -0.6586 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4699    1.0635    0.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5496    2.3396   -0.0106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9100    3.3615    0.9555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2254    4.2003    1.7643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2719    0.1561   -1.0714 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7320    2.2596    1.3995 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8275    0.6408   -1.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4108    2.4030    0.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7047    0.7218   -1.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989    2.2599   -1.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0647    1.3038    0.5391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3272   -1.3105   -0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8914   -0.3829    0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2278   -1.0510    2.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9447   -2.3402    1.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1499   -1.2650    1.6482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4586    0.3651    1.5807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0986   -1.9632   -1.9385 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2739   -2.4569   -0.8993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6766   -3.8749   -0.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -3.1525    0.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3183   -2.1174    1.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7425   -3.0220   -0.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1401   -0.5607   -0.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0445   -2.1561   -2.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0166    0.5039   -1.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6860    0.7928    1.3296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3295    2.5958   -1.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5162    4.9370    2.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5543   -0.2045   -1.9830 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  3  0
  6 21  1  0
 10 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  3  0
 16 14  1  0
 10 21  1  6
 15 41  1  0
 14 40  1  1
 13 38  1  0
 13 39  1  0
 12 36  1  0
 12 37  1  0
 11 34  1  0
 11 35  1  0
  9 32  1  0
  9 33  1  0
  8 30  1  0
  8 31  1  0
  7 28  1  0
  7 29  1  0
  6 27  1  1
  5 25  1  0
  5 26  1  0
  4 24  1  0
  3 23  1  0
  1 22  1  0
 21 46  1  0
 16 42  1  6
 17 43  1  0
 18 44  1  0
 20 45  1  0
M  END


  Mrv1652309032221132D          

 21 22  0  0  1  0            999 V2000
   -2.9980   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1895   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  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
 10 11  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
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  1  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  3  0  0  0  0
 10 21  1  6  0  0  0
  6 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0180805

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CCC[C@]2(CCC[C@@H](C\C=C\C#C)N2)[C@@H]1\C=C\C#C

> <INCHI_IDENTIFIER>
InChI=1S/C19H25NO/c1-3-5-7-10-16-11-8-14-19(20-16)15-9-13-18(21)17(19)12-6-4-2/h1-2,5-7,12,16-18,20-21H,8-11,13-15H2/b7-5+,12-6+/t16-,17-,18+,19-/m1/s1

> <INCHI_KEY>
JBRYWENFVHQBGY-GFSCOHCQSA-N

> <FORMULA>
C19H25NO

> <MOLECULAR_WEIGHT>
283.415

> <EXACT_MASS>
283.193614429

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
34.09061180449204

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,6R,7S,8S)-7-[(1E)-but-1-en-3-yn-1-yl]-2-[(2E)-pent-2-en-4-yn-1-yl]-1-azaspiro[5.5]undecan-8-ol

> <JCHEM_LOGP>
2.668694500666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.836896104235457

> <JCHEM_PKA_STRONGEST_BASIC>
10.518047537670068

> <JCHEM_POLAR_SURFACE_AREA>
32.26

> <JCHEM_REFRACTIVITY>
89.4867

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
histrionicotoxin

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.596  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.056  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.516  -0.564   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.746  -1.897   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.206  -1.897   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.954   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.954  -1.897   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -1.897   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.564  -3.231   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.206  -4.565   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       2.104  -0.564   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   16   21                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   10   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19                                                            
CONECT   21   10    6                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₅NO

Average Mass

283.4150 Da

Monoisotopic Mass

283.19361 Da

IUPAC Name

(2S,6R,7S,8S)-7-[(1E)-but-1-en-3-yn-1-yl]-2-[(2E)-pent-2-en-4-yn-1-yl]-1-azaspiro[5.5]undecan-8-ol

Traditional Name

histrionicotoxin

CAS Registry Number

Not Available

SMILES

O[C@H]1CCC[C@]2(CCC[C@@H](C\C=C\C#C)N2)[C@@H]1\C=C\C#C

InChI Identifier

InChI=1S/C19H25NO/c1-3-5-7-10-16-11-8-14-19(20-16)15-9-13-18(21)17(19)12-6-4-2/h1-2,5-7,12,16-18,20-21H,8-11,13-15H2/b7-5+,12-6+/t16-,17-,18+,19-/m1/s1

InChI Key

JBRYWENFVHQBGY-GFSCOHCQSA-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
Mantella madagascariensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as histrionicotoxins. These are frog toxins structurally characterized by the presence of a dodecahydropyrrolo[1,2-a]quinolin-1-yl}ethanol moiety or a 2,7-disubstituted 1-azaspiro[5.5]Undecan-8-ol moiety.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Histrionicotoxins

Sub Class

Not Available

Direct Parent

Histrionicotoxins

Alternative Parents

Substituents

Histrionicotoxin skeleton
Azaspirodecane
Piperidine
Cyclic alcohol
Secondary alcohol
Acetylide
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Organopnictogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

terminal acetylenic compound (CHEBI:34792 )
secondary alcohol (CHEBI:34792 )
azaspiro compound (CHEBI:34792 )
Alkaroids (C13683 )

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	2.67	ChemAxon
pKa (Strongest Acidic)	14.84	ChemAxon
pKa (Strongest Basic)	10.52	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	32.26 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.49 m³·mol⁻¹	ChemAxon
Polarizability	34.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00028347

Chemspider ID

4445422

KEGG Compound ID

C13683

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Histrionicotoxins

METLIN ID

Not Available

PubChem Compound

5282247

PDB ID

Not Available

ChEBI ID

34792

Good Scents ID

Not Available

References

General References

Jeckel AM, Bolton SK, Waters KR, Antoniazzi MM, Jared C, Matsumura K, Nishikawa K, Morimoto Y, Grant T, Saporito RA: Dose-dependent alkaloid sequestration and N-methylation of decahydroquinoline in poison frogs. J Exp Zool A Ecol Integr Physiol. 2022 Jun;337(5):537-546. doi: 10.1002/jez.2587. Epub 2022 Feb 24. [PubMed:35201668 ]
Matsumura K, Nishikawa K, Yoshida H, Niwa T, Fushii Y, Doe M, Morimoto Y: One-Step Synthesis of the 1-Azaspiro[5.5]undecane Skeleton Characteristic of Histrionicotoxin Alkaloids from Linear Substrates via Hg(OTf)(2) -Catalyzed Cycloisomerization. Chem Asian J. 2021 Jul 19;16(14):1882-1886. doi: 10.1002/asia.202100383. Epub 2021 May 26. [PubMed:33973732 ]
Shabir G, Saeed A, Ali F: A comparative study of synthetic approaches towards total synthesis of histrionicotoxin: a selective inhibitor of nicotinic acetylcholine receptors. J Asian Nat Prod Res. 2021 Oct;23(10):919-937. doi: 10.1080/10286020.2020.1810670. Epub 2020 Aug 24. [PubMed:32835524 ]
Jeckel AM, Matsumura K, Nishikawa K, Morimoto Y, Saporito RA, Grant T, Ifa DR: Use of whole-body cryosectioning and desorption electrospray ionization mass spectrometry imaging to visualize alkaloid distribution in poison frogs. J Mass Spectrom. 2020 Jun;55(6):e4520. doi: 10.1002/jms.4520. [PubMed:32452606 ]
Matsumura K, Nishikawa K, Yoshida H, Doe M, Morimoto Y: Formal total synthesis of histrionicotoxin alkaloids via Hg(OTf)(2)-catalyzed cycloisomerization and SmI(2)-induced ring expansion. RSC Adv. 2018 Mar 21;8(21):11296-11303. doi: 10.1039/c8ra02011f. eCollection 2018 Mar 21. [PubMed:35542821 ]
LOTUS database [Link]

Showing NP-Card for histrionicotoxin (NP0180805)

MOL for NP0180805 (histrionicotoxin)

3D MOL for NP0180805 (histrionicotoxin)

3D SDF for NP0180805 (histrionicotoxin)

3D-SDF for NP0180805 (histrionicotoxin)

PDB for NP0180805 (histrionicotoxin)

3D PDB for NP0180805 (histrionicotoxin)

SMILES for NP0180805 (histrionicotoxin)

INCHI for NP0180805 (histrionicotoxin)

Structure for NP0180805 (histrionicotoxin)

3D Structure for NP0180805 (histrionicotoxin)