NP-MRD: Showing NP-Card for oenanthotoxin (NP0198847)

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Record Information

Version

2.0

Created at

2022-09-04 17:22:00 UTC

Updated at

2022-09-04 17:22:00 UTC

NP-MRD ID

NP0198847

Secondary Accession Numbers

None

Natural Product Identification

Common Name

oenanthotoxin

Description

Oenanthotoxin, also known as OETX, belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms. Thus, oenanthotoxin is considered to be a fatty alcohol. oenanthotoxin is found in Oenanthe crocata and Oenanthe fistulosa. oenanthotoxin was first documented in 2014 (PMID: 25474700). Based on a literature review a small amount of articles have been published on Oenanthotoxin (PMID: 35189181) (PMID: 33506296) (PMID: 27693772) (PMID: 26211461).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 40  0  0  0  0  0  0  0  0999 V2000
   -7.4135    1.4177    0.8101 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0899   -0.0523    0.6929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6050   -0.3133    0.6951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9285    0.3909   -0.4685 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1322    1.7719   -0.3856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4362    0.1767   -0.4031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0590   -1.2962   -0.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5873   -1.3879   -0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7723   -0.3547   -0.2993 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6680   -0.5890   -0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5350    0.4020   -0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9481    0.1457   -0.0812 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1530   -0.0556   -0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5484   -0.2707    0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7440   -0.4408    0.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1752   -0.6306    0.2830 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0512    0.0140   -0.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5238   -0.1648   -0.3342 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0497    1.0967    0.0067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4245    1.5418    1.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6982    1.9581    1.4657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4740    1.9184   -0.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5541   -0.6648    1.4850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4610   -0.3740   -0.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1113   -0.0953    1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4900   -1.4158    0.5126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3150    0.0330   -1.4351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5605    2.2330   -1.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9774    0.7411   -1.2393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0399    0.5461    0.5712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4449   -1.7636   -1.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5064   -1.8521    0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1391   -2.3844   -0.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1823    0.6219   -0.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -1.5909   -0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1259    1.4099   -0.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5502   -1.3313    1.0101 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7030    0.7242   -1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9677   -0.5425   -1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6948   -0.8895    0.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8949    1.3167    0.9444 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
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  3  0
 13 14  1  0
 14 15  3  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  6
  5 28  1  0
  6 29  1  0
  6 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 11 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
M  END


  Mrv1652309042219222D          

 19 18  0  0  1  0            999 V2000
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9039    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7618    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4763    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1908    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9052    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6197    2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3342    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0487    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7631    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4776    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1921    3.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1921    4.3164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  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
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  3  0  0  0  0
 13 14  1  0  0  0  0
 14 15  3  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0198847

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC[C@@H](O)CC\C=C\C=C\C#CC#C\C=C\CO

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O2/c1-2-14-17(19)15-12-10-8-6-4-3-5-7-9-11-13-16-18/h4,6,8,10-11,13,17-19H,2,12,14-16H2,1H3/b6-4+,10-8+,13-11+/t17-/m1/s1

> <INCHI_KEY>
UPXPHJXYZGEBCW-SRFVWEJJSA-N

> <FORMULA>
C17H22O2

> <MOLECULAR_WEIGHT>
258.361

> <EXACT_MASS>
258.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
32.882202461884226

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,8E,10E,14R)-heptadeca-2,8,10-trien-4,6-diyne-1,14-diol

> <JCHEM_LOGP>
3.437551883333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.61881750820916

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.56561405595313

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2159292219093132

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
85.536

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
oenanthotoxin

> <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       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.287   1.127   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.288   3.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.622   2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.956   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.289   2.667   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.623   3.437   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.957   4.207   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.290   4.977   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.624   5.747   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.958   6.517   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      23.292   5.747   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      24.625   6.517   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      24.625   8.057   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

View in JSmol

Synonyms

Value	Source
Enanthotoxin	MeSH
2,8,10-Heptadecatriene-4,6-diyne-1,14-diol	MeSH
OETX	MeSH

Chemical Formula

C₁₇H₂₂O₂

Average Mass

258.3610 Da

Monoisotopic Mass

258.16198 Da

IUPAC Name

(2E,8E,10E,14R)-heptadeca-2,8,10-trien-4,6-diyne-1,14-diol

Traditional Name

oenanthotoxin

CAS Registry Number

Not Available

SMILES

CCC[C@@H](O)CC\C=C\C=C\C#CC#C\C=C\CO

InChI Identifier

InChI=1S/C17H22O2/c1-2-14-17(19)15-12-10-8-6-4-3-5-7-9-11-13-16-18/h4,6,8,10-11,13,17-19H,2,12,14-16H2,1H3/b6-4+,10-8+,13-11+/t17-/m1/s1

InChI Key

UPXPHJXYZGEBCW-SRFVWEJJSA-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
Oenanthe crocata	LOTUS Database	35616633
Oenanthe fistulosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohols

Direct Parent

Long-chain fatty alcohols

Alternative Parents

Substituents

Long chain fatty alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	3.44	ChemAxon
pKa (Strongest Acidic)	15.57	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	85.54 m³·mol⁻¹	ChemAxon
Polarizability	32.88 Å³	ChemAxon
Number of Rings	0	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

C00048029

Chemspider ID

24616929

KEGG Compound ID

C20044

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oenanthotoxin

METLIN ID

Not Available

PubChem Compound

44138996

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Gish A, Robveille C, Gicquel T, Allorge D, Gault G, Gaulier JM: Analytical documentation of an Arabian horse fatality related to Oenanthe crocata poisoning. Toxicon. 2022 Apr 30;210:39-43. doi: 10.1016/j.toxicon.2022.02.009. Epub 2022 Feb 18. [PubMed:35189181 ]
Martinez P, Quintela O, Del Valle E, Perez-Gomez B: Genetic identification and subsequent LC-QTOF MS analysis of plant remains (Oenanthe spp.) could prove the cause of an undetermined sudden death. Int J Legal Med. 2021 Jul;135(4):1407-1411. doi: 10.1007/s00414-020-02488-6. Epub 2021 Jan 27. [PubMed:33506296 ]
Lin M, Zhang W, Su J: Toxic polyacetylenes in the genus Bupleurum (Apiaceae) - Distribution, toxicity, molecular mechanism and analysis. J Ethnopharmacol. 2016 Dec 4;193:566-573. doi: 10.1016/j.jep.2016.09.052. Epub 2016 Sep 30. [PubMed:27693772 ]
Sommerwerk S, Heller L, Siewert B, Csuk R: Chemoenzymatic synthesis and cytotoxicity of oenanthotoxin and analogues. Bioorg Med Chem. 2015 Sep 1;23(17):5595-602. doi: 10.1016/j.bmc.2015.07.031. Epub 2015 Jul 22. [PubMed:26211461 ]
Czyzewska MM, Chrobok L, Kania A, Jatczak M, Pollastro F, Appendino G, Mozrzymas JW: Dietary acetylenic oxylipin falcarinol differentially modulates GABAA receptors. J Nat Prod. 2014 Dec 26;77(12):2671-7. doi: 10.1021/np500615j. Epub 2014 Dec 4. [PubMed:25474700 ]
LOTUS database [Link]

Showing NP-Card for oenanthotoxin (NP0198847)

MOL for NP0198847 (oenanthotoxin)

3D MOL for NP0198847 (oenanthotoxin)

3D SDF for NP0198847 (oenanthotoxin)

3D-SDF for NP0198847 (oenanthotoxin)

PDB for NP0198847 (oenanthotoxin)

3D PDB for NP0198847 (oenanthotoxin)

SMILES for NP0198847 (oenanthotoxin)

INCHI for NP0198847 (oenanthotoxin)

Structure for NP0198847 (oenanthotoxin)

3D Structure for NP0198847 (oenanthotoxin)