ContaminantDB: (-)-Eburnamonine

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

Record Information

Version

1.0

Creation Date

2016-05-22 05:01:48 UTC

Update Date

2026-04-14 19:32:41 UTC

Accession Number

CHEM018144

Identification

Common Name

(-)-Eburnamonine

Class

Small Molecule

Description

Contaminant Sources

STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Cervoxan	Kegg
(-)-Eburnamonine	MeSH
Eburnamonine phosphate, (3alpha,16alpha)-isomer	MeSH
Eburnamonine	MeSH
Eburnamonine monohydrochloride, (3alpha,16alpha)-isomer	MeSH
Eburnamonine, (3alpha,16alpha)-isomer	MeSH

Chemical Formula

C₁₉H₂₂N₂O

Average Molecular Mass

294.398 g/mol

Monoisotopic Mass

294.173 g/mol

CAS Registry Number

4880-88-0

IUPAC Name

(15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.0²,⁷.0⁸,¹⁸.0¹⁵,¹⁹]nonadeca-2,4,6,8(18)-tetraen-17-one

Traditional Name

vinburnine

SMILES

[H][C@]12N3CCC[C@@]1(CC)CC(=O)N1C4=CC=CC=C4C(CC3)=C21

InChI Identifier

InChI=1S/C19H22N2O/c1-2-19-9-5-10-20-11-8-14-13-6-3-4-7-15(13)21(16(22)12-19)17(14)18(19)20/h3-4,6-7,18H,2,5,8-12H2,1H3/t18-,19+/m1/s1

InChI Key

WYJAPUKIYAZSEM-MOPGFXCFSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as eburnan-type alkaloids. These are alkaloids with a structure based on the eburnan skeleton, that arises from rearrangement of the aspidospermidine ring system, involving migration of C-21 from C-7 to C-2, fission of the 2,16-bond, and attachment of C-16 to N-1.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Eburnan-type alkaloids

Sub Class

Not Available

Direct Parent

Eburnan-type alkaloids

Alternative Parents

Substituents

Eburna alkaloid
Indolo[3,2-1de][1,5]naphthyridine
Beta-carboline
Pyridoindole
Diazanaphthalene
Naphthyridine
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Piperidine
Benzenoid
Heteroaromatic compound
Pyrrole
Tertiary amine
Lactam
Tertiary aliphatic amine
Azacycle
Organoheterocyclic compound
Amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

alkaloid (CHEBI:4740 )
Indole alkaloids (C09149 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

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

Not Available

Appearance

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	3.3	ALOGPS
logP	2.74	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	19.25	ChemAxon
pKa (Strongest Basic)	6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	25.24 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	87.05 m³·mol⁻¹	ChemAxon
Polarizability	33.67 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-000b-2790000000-d9b39542541cd67b85fa	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-000b-2790000000-d9b39542541cd67b85fa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0090000000-13f9d8889268d6881423	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0090000000-c00308b130e91cfa6bf6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0v00-0090000000-eba88d12e6c6482c7909	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-2de3698bc1b14beaffcc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-1090000000-373e991dfa5140c62e0f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02dj-4090000000-550185cccc74ff4b15f2	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)

Not Available

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

DB13793

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001714

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Vinburnine

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

71203

Kegg Compound ID

C09149

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

(-)-Eburnamonine (CHEM018144)

Structure for CHEM018144: (-)-Eburnamonine