ContaminantDB: Thalidomide arene oxide

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

Record Information

Version

1.0

Creation Date

2016-05-25 18:17:13 UTC

Update Date

2016-11-09 01:17:24 UTC

Accession Number

CHEM021974

Identification

Common Name

Thalidomide arene oxide

Class

Small Molecule

Description

Thalidomide arene oxide is a metabolic intermediate of thalidomide which subsequently converts to 5-hydroxythalidomide. It belongs to the family of Isoindolones. These are aromatic polycyclic compounds that an isolindole bearing a ketone.

Contaminant Sources

HMDB Contaminants - Urine

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₃H₁₀N₂O₅

Average Molecular Mass

274.229 g/mol

Monoisotopic Mass

274.059 g/mol

CAS Registry Number

1488-25-1

IUPAC Name

3-{3,5-dioxo-1aH,3H,4H,5H,6aH-oxireno[2,3-f]isoindol-4-yl}piperidine-2,6-dione

Traditional Name

3-{3,5-dioxo-1aH,6aH-oxireno[2,3-f]isoindol-4-yl}piperidine-2,6-dione

SMILES

O=C1N(C2CCC(=O)NC2=O)C(=O)C2=CC3OC3C=C12

InChI Identifier

InChI=1S/C13H10N2O5/c16-10-2-1-7(11(17)14-10)15-12(18)5-3-8-9(20-8)4-6(5)13(15)19/h3-4,7-9H,1-2H2,(H,14,16,17)

InChI Key

MNALUCRLHVMELD-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindolines

Direct Parent

Isoindolones

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Isoindolone
Isoindole
Piperidinedione
Delta-lactam
Piperidinone
Carboxylic acid imide, n-substituted
Piperidine
N-alkylpyrrolidine
2-pyrrolidone
Pyrrolidone
Carboxylic acid imide
Dicarboximide
Carboxylic acid imide, n-unsubstituted
Pyrrolidine
Lactam
Ether
Oxirane
Dialkyl ether
Oxacycle
Azacycle
Carboxylic acid derivative
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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	9.74 g/L	ALOGPS
logP	-0.2	ALOGPS
logP	-1.4	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	11.59	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	96.08 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	64.8 m³·mol⁻¹	ChemAxon
Polarizability	25.06 Å³	ChemAxon
Number of Rings	4	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 GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f7o-6590000000-a7fc735d7e78836a2b05	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-1a6c97be171d50b6ebce	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kdi-1190000000-69e7b3abdde425feff1b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9310000000-13b91ffd1863719a04dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0190000000-557e4588bda387c27cfc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-022c-3490000000-f29bce6422796af5d7ba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ox-9300000000-cfdab0e72454036ba4c8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0790000000-378e78b08711044e8368	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01t9-0490000000-31ef1188d9e6391ea596	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fmj-0950000000-d0d3bd1eb82162de1280	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0290000000-f3011e6c100397dfbd06	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-1490000000-a4efeb2dd36428018fab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01vo-4920000000-915e71e92e800217921e	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	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

HMDB0013872

FooDB ID

Not Available

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

35032775

ChEBI ID

Not Available

PubChem Compound ID

88553247

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1.

Thalidomide arene oxide (CHEM021974)

Structure for CHEM021974: Thalidomide arene oxide