CAS 636-20-4|CAS 533-48-2|desthiobiotin|DL-DESTHIOBIOTIN|6-(5-methyl-2-oxoimidazolidin-4-yl)hexanoic acid|(±)-Desthiobiotin|cis-(±)-5-Methyl-2-oxo-4-imidazolidinehexanoic Acid|cis-5-Methyl-2-oxo-4...

General Information

Structure

Molecular Formula

C₁₀H₁₈N₂O₃

Molecular Mass

214.26152

Exact Mass

214.13174245

Charge

InChI

InChI=1S/C10H18N2O3/c1-7-8(12-10(15)11-7)5-3-2-4-6-9(13)14/h7-8H,2-6H2,1H3,(H,13,14)(H2,11,12,15)

InChIKey

AUTOLBMXDDTRRT-UHFFFAOYSA-N

Canonic Smiles

OC(=O)CCCCCC1NC(=O)NC1C

Isomeric Smiles

CC1NC(=O)NC1CCCCCC(=O)O

Calculated Properties

JChem

LogD (pH = 7.4)

-1.97

LogD (pH = 5.5)

-0.19

Log P

0.73

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

4.63

Polar Surface Area

78.43

Polarizability

23.20

Molar Refractivity

54.40

LOG S

-1.08

Data Source

Commercial Catalog

Academic Data

643

Data Source

Names and Identifiers

IUPAC Traditional name

desthiobiotin dethiobiotin

Synonyms

DL-DESTHIOBIOTIN(±)-Desthiobiotincis-(±)-5-Methyl-2-oxo-4-imidazolidinehexanoic Acidcis-5-Methyl-2-oxo-4-imidazolidinehexanoic Acid(±)-Dethiobiotindl-Desthiobiotinrac-Desthio Biotindl-DethiobiotinNSC 203773(4R,5S)-rel-5-Methyl-2-oxo-4-imidazolidinehexanoic AciddethiobiotinDethiobiotinDesthiobiotin

IUPAC name

6-(5-methyl-2-oxoimidazolidin-4-yl)hexanoic acid

Names and Identifiers

Registration numbers

CAS Number

636-20-4533-48-2

PubChem SID

1620940068144669

PubChem CID

643

UniProt Database

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

SABIO-RK Database

137303011

SureChEMBL Database

SCHEMBL143997

CHEMBL

CHEMBL4585840

ACToR Database

15720-25-9636-20-417866-65-8

Reaxys Registry

84958

PubMed Citation Links

216215021273040722326745

KNApSAcK Database

C00000757

CHEBI ID

CHEBI:23649CHEBI:4457CHEBI:16691CHEBI:14132

KEGG ID

C01909

Patent number

EP0892066US2005208598US2007197427US2005271673US2006051811

BRENDA Database

6.2.1.11

Beilstein Number

177518

HMDB Database

HMDB0003581

Registration numbers

Properties

Safety Information

MSDS Link

Download link

Product Information

Certificate of Analysis

Download link

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

05205919

MP Biomedicals Rare Chemical collection

TRC

D297490

rac-Desthiobiotin is useful as an intermediate in the synthesis of Biotin. The conversion of Dethiobiotin into Biotin was studied in Escherichia coli by starting from specifically deuterated precursors.

ChEBI

CHEBI:16691

A hexanoic acid having a 5-methyl-2-oxoimidazolidin-4-yl group at the 6-position.

Molecule Details

References

PubChem Literature

From Data Sources

• Li, H.-C., et al.: J. Biol. Chem., 243, 4391 (1976)

• Tsuboi, T., et al.: Chem. Pharmaceut. Bull., 24, 1123 (1976)

References

Bioactivity

PubChem BioAssay