Human Metabolome Database: Showing metabocard for Thalidomide arene oxide (HMDB0013872)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:00:17 UTC

Update Date

2017-12-07 02:44:01 UTC

HMDB ID

HMDB0013872

Secondary Accession Numbers

HMDB13872

Metabolite Identification

Common Name

Thalidomide arene oxide

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.

Structure

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

Synonyms

Not Available

Chemical Formula

C₁₃H₁₀N₂O₅

Average Molecular Weight

274.2289

Monoisotopic Molecular Weight

274.05897144

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

CAS Registry Number

1488-25-1

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

This compound 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

Ontology

Disposition

Source:

Endogenous

Biological location:

Organ and components:

Cell and elements:

Extracellular

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f7o-6590000000-a7fc735d7e78836a2b05	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-1a6c97be171d50b6ebce	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0kdi-1190000000-69e7b3abdde425feff1b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9310000000-13b91ffd1863719a04dd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0190000000-557e4588bda387c27cfc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-022c-3490000000-f29bce6422796af5d7ba	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ox-9300000000-cfdab0e72454036ba4c8	View in MoNA

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Urine

Tissue Location

Kidney
Liver

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified		Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details
Urine	Expected but not Quantified		Not Available	Not Available	Taking drug identified by DrugBank entry	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

88553247

PDB ID

Not Available

ChEBI ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [PubMed:19515014 ]

Showing metabocard for Thalidomide arene oxide (HMDB0013872)

Structure for HMDB0013872 (Thalidomide arene oxide)