4-nitrophenyl 5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoate

• ChemBase ID: 133750
• Molecular Formular: C16H19N3O5S
• Molecular Mass: 365.40416
• Monoisotopic Mass: 365.10454172
• SMILES: c1cc(ccc1[N+](=O)[O-])OC(=O)CCCC[C@H]1[C@@H]2[C@H](CS1)NC(=O)N2
• Canonical SMILES: O=C1N[C@@H]2[C@H](N1)[C@@H](SC2)CCCCC(=O)Oc1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C16H19N3O5S/c20-14(24-11-7-5-10(6-8-11)19(22)23)4-2-1-3-13-15-12(9-25-13)17-16(21)18-15/h5-8,12-13,15H,1-4,9H2,(H2,17,18,21)/t12-,13-,15-/m0/s1
• InChIKey: YUDNXDTXQPYKCA-YDHLFZDLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-nitrophenyl 5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoate
• IUPAC Traditional name: 4-nitrophenyl 5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanoate
• Synonyms: BNP; (+)-Biotin 4-nitrophenyl ester; 4-Nitrophenyl (+)-biotinate; d-Biotin p-nitrophenyl ester; 4-硝基苯基 (+)-生物素酯; d-生物素对硝基苯酯; (+)-生物素 4-硝基苯酯

Database IDs

• CAS Number: 33755-53-2
• MDL Number: MFCD15141972
• Beilstein Number: 5795805
• PubChem SID: 162228027; 24888552
• PubChem CID: 83848

CALCULATED PROPERTIES

• Acid pKa: 13.1003895
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.0632603
• LogD (pH = 7.4): 2.0632596
• Log P: 2.0632603
• Molar Refractivity: 90.9181 cm^3
• Polarizability: 35.41273 Å^3
• Polar Surface Area: 110.57 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: methanol: soluble25 mg/mL, clear, colorless to greenish-yellow
• Melting Point: 163-165 °C; 163-165 °C(lit.); 163-165°C
• Optical Rotation: [α]20/D +50±2°, c = 1% in DMF; [α]25/D +51°, c = 2 in DMF: AcOH (99:1); +51 (c=2 in DMF:AcOH)

Safety Information

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

Product Information

• Purity: ≥98.0% (HPLC); 98%
• Empirical Formula (Hill Notation): C16H19N3O5S

DETAILS

Sigma Aldrich - 861650

Packaging
100 mg in glass bottle

Sigma Aldrich - 14406

Other Notes
The avidin-reactive biotinyl derivative - a tool in biochemistry, review 1; Coupling of biotinyl residues to peptides 2