ContaminantDB: Vindoline

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

Record Information

Version

1.0

Creation Date

2014-08-29 04:59:09 UTC

Update Date

2026-05-20 21:30:35 UTC

Accession Number

CHEM003015

Identification

Common Name

Vindoline

Class

Small Molecule

Description

Vindoline is a chemical precursor to vinblastine.

Contaminant Sources

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
Vindoline, citrate, (2beta,3beta,4beta,5alpha,12beta,19alpha)-isomer	MeSH
Vindoline, monohydrochloride, (2beta,3beta,4beta,5alpha,12beta,19alpha)-isomer	MeSH

Chemical Formula

C₂₅H₃₂N₂O₆

Average Molecular Mass

456.531 g/mol

Monoisotopic Mass

456.226 g/mol

CAS Registry Number

Not Available

IUPAC Name

Not Available

Traditional Name

vindolin

SMILES

[H][C@@]12N(C)C3=C(C=CC(OC)=C3)[C@@]11CCN3CC=C[C@](CC)([C@@]13[H])[C@@]([H])(OC(C)=O)[C@]2(O)C(=O)OC

InChI Identifier

InChI=1S/C25H32N2O6/c1-6-23-10-7-12-27-13-11-24(19(23)27)17-9-8-16(31-4)14-18(17)26(3)20(24)25(30,22(29)32-5)21(23)33-15(2)28/h7-10,14,19-21,30H,6,11-13H2,1-5H3/t19-,20+,21+,23+,24+,25-/m0/s1

InChI Key

CXBGOBGJHGGWIE-ACSXSLCXSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as plumeran-type alkaloids. These are alkaloids with a structure based on the plumeran skeleton. Plumeran is a pentacyclic compound that consists of a pyrrolidine ring shed to the quinoline moiety of pyrido[3,2-c]carbazole ring system.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Plumeran-type alkaloids

Sub Class

Not Available

Direct Parent

Plumeran-type alkaloids

Alternative Parents

Substituents

Plumeran-type alkaloid
Carbazole
Indole or derivatives
Anisole
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Alkyl aryl ether
Aralkylamine
N-alkylpyrrolidine
Benzenoid
Dicarboxylic acid or derivatives
Methyl ester
Cyclic alcohol
Tertiary alcohol
Pyrrolidine
Tertiary aliphatic amine
Tertiary amine
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Ether
Organic nitrogen compound
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Indole alkaloids (C01626 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Microtubule
Plasma Membrane
Tubulin

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Insulin secretion	Not Available	map04911
Quinolines	Not Available	Not Available
Metabolic Pathways	Not Available	Not Available
Indole Alkaloid Biosynthesis	Not Available	Not Available
Glutathione Metabolism	SMP00015	map00480

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	0.39 g/L	ALOGPS
logP	2.53	ALOGPS
logP	1.88	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	10.87	ChemAxon
pKa (Strongest Basic)	8.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	88.54 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.3 m³·mol⁻¹	ChemAxon
Polarizability	47.72 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0003900000-243b54421f754c8830a6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05mk-0008900000-29540fbd94603560f89d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000b-2019000000-bf56c984bb73bd05e9d9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4j-2005900000-d0ef101d821064b0cb3c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bta-4007900000-207e25f34cbcf9ba0c3c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-8109000000-923bd24d9e7821d851d4	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)

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

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

C00024613

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Vindoline

Chemspider ID

Not Available

ChEBI ID

16380

PubChem Compound ID

260535

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Vindoline (CHEM003015)

Structure for CHEM003015: Vindoline