ContaminantDB: vellosimine

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

Record Information

Version

1.0

Creation Date

2016-05-27 02:03:14 UTC

Update Date

2016-11-09 01:22:40 UTC

Accession Number

CHEM042451

Identification

Common Name

vellosimine

Class

Small Molecule

Description

Vellosimine is a member of the class of compounds known as macroline alkaloids. Macroline alkaloids are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids. Vellosimine is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Vellosimine can be found in a number of food items such as caraway, italian oregano, star anise, and fox grape, which makes vellosimine a potential biomarker for the consumption of these food products.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

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

Synonyms

Value	Source
(+)-Vellosimine	MeSH

Chemical Formula

C₁₉H₂₀N₂O

Average Molecular Mass

292.382 g/mol

Monoisotopic Mass

292.158 g/mol

CAS Registry Number

Not Available

IUPAC Name

15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carbaldehyde

Traditional Name

15-ethylidene-3,17-diazapentacyclo[12.3.1.0²,¹⁰.0⁴,⁹.0¹²,¹⁷]octadeca-2(10),4,6,8-tetraene-13-carbaldehyde

SMILES

CC=C1CN2C3CC4=C(NC5=CC=CC=C45)C2CC1C3C=O

InChI Identifier

InChI=1S/C19H20N2O/c1-2-11-9-21-17-8-14-12-5-3-4-6-16(12)20-19(14)18(21)7-13(11)15(17)10-22/h2-6,10,13,15,17-18,20H,7-9H2,1H3

InChI Key

MHASSCPGKAMILD-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as macroline alkaloids. These are alkaloids with a structure that is based on the tetracyclic macroline skeleton. The macroline skeleton arises by scission of the C-21 to N-4 bond of the akuammilan skeleton, and mostly occurs in bisindole alkaloids.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Macroline alkaloids

Sub Class

Not Available

Direct Parent

Macroline alkaloids

Alternative Parents

Substituents

Macroline skeleton
Sarpagine-skeleton
Vobasan skeleton
Beta-carboline
Pyridoindole
3-alkylindole
Indole
Indole or derivatives
Quinuclidine
Aralkylamine
Benzenoid
Piperidine
Heteroaromatic compound
Pyrrole
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aldehyde
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (VELLOSIMINE )

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	0.1 g/L	ALOGPS
logP	2.51	ALOGPS
logP	2.46	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	15.29	ChemAxon
pKa (Strongest Basic)	5.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	36.1 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	88.18 m³·mol⁻¹	ChemAxon
Polarizability	33.33 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-502966b71b3fa4b51088	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0090000000-8c8a72ed22a2c42f48f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-005a-0980000000-393d345529d5f12f002e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-eb9636b759144711f704	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ox-0090000000-1377844617e62b912753	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-0090000000-c96869b275c60a9d52bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0090000000-30850ca9637e3e228dfd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002f-0090000000-ac575a3d12360d46fa43	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0900000000-a66b6223d1fbd7db0b92	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0090000000-74a3146908205cd6ebec	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0090000000-60735b38d43fc092aca2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01p9-0190000000-a1d7ba384146d50c2c3f	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

Not Available

HMDB ID

Not Available

FooDB ID

FDB031253

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

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

3666703

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

vellosimine (CHEM042451)

Structure for CHEM042451: vellosimine