ContaminantDB: Senkirkine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-08-29 05:03:50 UTC

Update Date

2026-05-20 18:34:15 UTC

Accession Number

CHEM003039

Identification

Common Name

Senkirkine

Class

Small Molecule

Description

Senkirkine, present in coltsfoot, have the highest mutagenetic activity of any pyrrolozidine alkaloid.

Contaminant Sources

IARC Carcinogens Group 3
T3DB toxins

Contaminant Type

Amine
Ester
Ether
Natural Compound
Organic Compound
PFAS
Phytotoxin
Plant Toxin

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Senkirkine, (15E)-isomer	MeSH
Neosenkirkine	MeSH

Chemical Formula

C₁₉H₂₇NO₆

Average Molecular Mass

365.421 g/mol

Monoisotopic Mass

365.184 g/mol

CAS Registry Number

2318-18-5

IUPAC Name

Not Available

Traditional Name

renardine

SMILES

[H]\C(C)=C1/C[C@@]([H])(C)[C@@](C)(O)C(=O)OC\C2=C([H])\CN(C)CC[C@@]([H])(OC1=O)C2=O

InChI Identifier

InChI=1S/C19H27NO6/c1-5-13-10-12(2)19(3,24)18(23)25-11-14-6-8-20(4)9-7-15(16(14)21)26-17(13)22/h5-6,12,15,24H,7-11H2,1-4H3/b13-5-,14-6-/t12-,15-,19-/m1/s1

InChI Key

HPDHKHMHQGCNPE-QLJRNOHWSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Alpha-acyloxy ketone
Dicarboxylic acid or derivatives
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Carboxylic acid ester
Ketone
Lactone
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Azacycle
Carbonyl group
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Alcohol
Amine
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

macrolide (CHEBI:9111 )
Pyrrolizidine alkaloids (C10396 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	5.46 g/L	ALOGPS
logP	1.49	ALOGPS
logP	1.89	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.37	ChemAxon
pKa (Strongest Basic)	6.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	93.14 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	96.98 m³·mol⁻¹	ChemAxon
Polarizability	37.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0309000000-6904fccbf21b53d56628	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-5915000000-c68922b3fa634ab83a53	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kai-9500000000-fa99de28b1ac7e31b891	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-044i-0609000000-f22ea04188dc5872bfc3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1905000000-449a234d9554a84646ca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00si-9801000000-06eda6130dd54fde5327	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0fr6-6920000000-aeb989c552f887cf7923	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (1)

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

C00002119

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

5281752

Kegg Compound ID

C10396

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Senkirkine (CHEM003039)

Structure for CHEM003039: Senkirkine