6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanoic acid

• ChemBase ID: 2839
• Molecular Formular: C16H27N3O4S
• Molecular Mass: 357.46828
• Monoisotopic Mass: 357.17222736
• SMILES: N1[C@@H]2[C@H](NC1=O)[C@@H](SC2)CCCCC(=O)NCCCCCC(=O)O
• Canonical SMILES: O=C(NCCCCCC(=O)O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C16H27N3O4S/c20-13(17-9-5-1-2-8-14(21)22)7-4-3-6-12-15-11(10-24-12)18-16(23)19-15/h11-12,15H,1-10H2,(H,17,20)(H,21,22)(H2,18,19,23)/t11-,12-,15-/m0/s1
• InChIKey: CMUGHZFPFWNUQT-HUBLWGQQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanoic acid
• IUPAC Traditional name: 6-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}hexanoic acid
• Synonyms: 6-[5-(2-Oxo-Hexahydro-Thieno[3,4-D]Imidazol-4-Yl)-Pentanoylamino]-Hexanoic Acid; 6-[[5-[(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-1-oxopentyl]amino]hexanoic Acid; 6-[(Biotinyl)amino]hexanoic acid; Biotin X; N-Biotinylcaproic Acid; (+)-Biotin-ε-aminocaproic acid; 6-((Biotinoyl)amino)hexanoic acid; Biotin-X; N-(+)-Biotinyl-6-aminocaproic acid; N-(+)-Biotinyl-6-aminohexanoic acid

Database IDs

• CAS Number: 72040-64-3
• MDL Number: MFCD00144853
• Beilstein Number: 706392
• PubChem SID: 46507521; 160966287
• PubChem CID: 446905

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.471876
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -0.4367284
• LogD (pH = 7.4): -2.2026417
• Log P: 0.62895167
• Molar Refractivity: 91.5108 cm^3
• Polarizability: 35.958576 Å^3
• Polar Surface Area: 107.53 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.06
• LOG S: -3.71
• Solubility (Water): 6.93e-02 g/l

PROPERTIES

Physical Property

• Solubility: DMF; DMF: soluble (pH>6); DMSO
• Apperance: solid; White Solid
• Melting Point: 222-227°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C16H27N3O4S

DETAILS

DrugBank - DB03139

Drug information: experimental

Sigma Aldrich - B7181

Application
Biotinylation reagent

Toronto Research Chemicals - B395670

An active Biotinylation reagent.

REFERENCES

• Giubellino, A., et al.: J. Med. Chem., 51, 7459 (2008)
• Wang, Z., et al.: Nat. Chem. Biol., 4, 557 (2008)