ContaminantDB: Retronecine

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

Record Information

Version

1.0

Creation Date

2014-08-29 04:59:53 UTC

Update Date

2016-11-09 01:09:01 UTC

Accession Number

CHEM003020

Identification

Common Name

Retronecine

Class

Small Molecule

Description

Retronecine is a pyrrolizidine alkaloid found in a variety of plants in the genera Senecio and Crotalaria, and the family Boraginaceae. It is the most common central core for other pyrrolizidine alkaloids.

Contaminant Sources

T3DB toxins

Contaminant Type

Amine
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

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

Synonyms

Value	Source
Retronecine, monohydrochloride, (1S-trans)-isomer	MeSH
Retronecine, monohydrochloride, (1S-cis)-isomer	MeSH
Heliotridine	MeSH
Retronecine, (1S-cis)-isomer	MeSH

Chemical Formula

C₈H₁₃NO₂

Average Molecular Mass

155.194 g/mol

Monoisotopic Mass

155.095 g/mol

CAS Registry Number

480-85-3

IUPAC Name

(1R,7aR)-7-(hydroxymethyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-ol

Traditional Name

retronecine

SMILES

[H][C@@]1(O)CCN2CC=C(CO)[C@]12[H]

InChI Identifier

InChI=1S/C8H13NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h1,7-8,10-11H,2-5H2/t7-,8-/m1/s1

InChI Key

HJSJELVDQOXCHO-HTQZYQBOSA-N

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
N-alkylpyrrolidine
1,3-aminoalcohol
Pyrrolidine
Pyrroline
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Organooxygen compound
Organonitrogen compound
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

pyrrolizines (CHEBI:8821 )
Pyrrolizidine alkaloids (C06177 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Microsome

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Dna replication	Not Available	map03030

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	119°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	649 g/L	ALOGPS
logP	-0.61	ALOGPS
logP	-1.2	ChemAxon
logS	0.62	ALOGPS
pKa (Strongest Acidic)	14.39	ChemAxon
pKa (Strongest Basic)	8.05	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	42.92 m³·mol⁻¹	ChemAxon
Polarizability	16.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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	splash10-000i-0900000000-4840a2db55d2c1385e1c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-1900000000-f6588f55c0c4126f67a7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00yr-9300000000-5cc63a3267b649d77c05	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-51963b5c9d214d8efcc9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0abi-0900000000-6c29cf2f2278b9238788	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05o1-9200000000-a08cfa1deae0e4dd944f	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Retronecine is classified as a pyrrolizidine alkaloid (PA). Unsaturated pyrrolizidine alkaloids are hepatotoxic, that is, damaging to the liver. PAs also cause hepatic veno-occlusive disease and liver cancer. PAs are tumorigenic. Disease associated with consumption of PAs is known as pyrrolizidine alkaloidosis. (Wikipedia)

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Retronecine is a pyrrolizidine alkaloid found in a variety of plants in the genera Senecio and Crotalaria, and the family Boraginaceae.

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

C00002108

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Retronecine

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

10198

Kegg Compound ID

C06177

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Retronecine (CHEM003020)

Structure for CHEM003020: Retronecine