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

• ChemBase ID: 158630
• Molecular Formular: C23H40F3N5O5S
• Molecular Mass: 555.6544096
• Monoisotopic Mass: 555.27022507
• SMILES: C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)NCCCCCC(=O)NCCCCCN)NC(=O)N2.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.NCCCCCNC(=O)CCCCCNC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C21H39N5O3S.C2HF3O2/c22-12-6-2-8-14-24-18(27)10-3-1-7-13-23-19(28)11-5-4-9-17-20-16(15-30-17)25-21(29)26-20;3-2(4,5)1(6)7/h16-17,20H,1-15,22H2,(H,23,28)(H,24,27)(H2,25,26,29);(H,6,7)/t16-,17-,20-;/m0./s1
• InChIKey: VBADGRRGBWPZBC-KYCOEFPESA-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}-N-(5-aminopentyl)hexanamide; trifluoroacetic acid
• IUPAC Traditional name: 6-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}-N-(5-aminopentyl)hexanamide; trifluoroacetic acid
• Synonyms: Biotin-X cadaverine; 5-([(N-(Biotinoyl)amino)hexanoyl]amino)pentylamine trifluoroacetate salt

Database IDs

• MDL Number: MFCD03427592
• PubChem SID: 162252766
• PubChem CID: 71312666

CALCULATED PROPERTIES

• Acid pKa: 13.491791
• H Acceptors: 4
• H Donor: 5
• LogD (pH = 5.5): -2.753398
• LogD (pH = 7.4): -2.333586
• Log P: 0.2705924
• Molar Refractivity: 120.2905 cm^3
• Polarizability: 47.327374 Å^3
• Polar Surface Area: 125.35 Å^2
• Rotatable Bonds: 17
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Empirical Formula (Hill Notation): C23H40F3N5O5S

DETAILS

Sigma Aldrich - B7306

Application
An amine-containing biotin derivative that serves as a versatile intermediate for the coupling of biotin to DNA, carboxylic acids, and other biomolecules. Also noted for use in transglutaminase-mediated modification of glutamine residues in cells and certain proteins.