Metabolite Thalidomide arene oxide

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

Similar Structures

Synonyms

Not Available

UNII

Not Available

CAS number

Not Available

Weight

Average: 274.2289
Monoisotopic: 274.05897144

Chemical Formula

C₁₃H₁₀N₂O₅

InChI Key

MNALUCRLHVMELD-UHFFFAOYSA-N

InChI

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)

IUPAC Name

4-(6-hydroxy-2-oxo-2,3,4,5-tetrahydropyridin-3-yl)-1aH,3H,4H,5H,6aH-oxireno[2,3-f]isoindole-3,5-dione

SMILES

OC1=NC(=O)C(CC1)N1C(=O)C2=CC3OC3C=C2C1=O

Reactions

Thalidomide

Thalidomide arene oxide
- Thalidomide arene oxide
  
  5-Hydroxythalidomide

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0f7o-6590000000-a7fc735d7e78836a2b05
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-03fr-0950000000-5c78270497dbb55a44f6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00di-0090000000-c027ab352b4a070fdcb2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004i-0390000000-11c0f4b97ff19c384efe
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0229-1390000000-5241ccf405c883e2bcf8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0ukd-3950000000-537849daf31925fa842d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-006x-2920000000-6940fa525db5a45bdf1b

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	168.2808745	predicted	DarkChem Lite v0.1.0
[M-H]-	160.03844	predicted	DeepCCS 1.0 (2019)
[M+H]+	168.5677745	predicted	DarkChem Lite v0.1.0
[M+H]+	162.40062	predicted	DeepCCS 1.0 (2019)
[M+Na]+	168.6735745	predicted	DarkChem Lite v0.1.0
[M+Na]+	168.48958	predicted	DeepCCS 1.0 (2019)

External Links

Human Metabolome Database: HMDB0013872
ChemSpider: 35032775

Predicted Properties

Property	Value	Source
Water Solubility	2.14 mg/mL	ALOGPS
logP	-0.31	ALOGPS
logP	-1.1	Chemaxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	3.03	Chemaxon
pKa (Strongest Basic)	-3.3	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	6	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	99.57 Å²	Chemaxon
Rotatable Bond Count	1	Chemaxon
Refractivity	65.13 m³·mol^-1	Chemaxon
Polarizability	24.9 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

Metabolite Thalidomide arene oxide

Structure for Thalidomide arene oxide

Collision Cross Sections (CCS)