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

• ChemBase ID: 155905
• Molecular Formular: C17H21N3O4S
• Molecular Mass: 363.43134
• Monoisotopic Mass: 363.12527717
• SMILES: c1cc(ccc1C(=O)O)NC(=O)CCCC[C@H]1[C@@H]2[C@H](CS1)NC(=O)N2
• Canonical SMILES: O=C(Nc1ccc(cc1)C(=O)O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C17H21N3O4S/c21-14(18-11-7-5-10(6-8-11)16(22)23)4-2-1-3-13-15-12(9-25-13)19-17(24)20-15/h5-8,12-13,15H,1-4,9H2,(H,18,21)(H,22,23)(H2,19,20,24)/t12-,13-,15-/m0/s1
• InChIKey: PVMDAMXGKHIMSQ-YDHLFZDLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}benzoic acid
• IUPAC Traditional name: 4-{5-[(3aS,4S,6aR)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanamido}benzoic acid
• Synonyms: B-PABA; N-(+)-Biotinyl-4-aminobenzoic acid

Database IDs

• CAS Number: 6929-40-4
• MDL Number: MFCD00077915
• Beilstein Number: 50100
• PubChem SID: 162250043; 24848629
• PubChem CID: 151442

CALCULATED PROPERTIES

• Acid pKa: 4.1605372
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): 0.05520591
• LogD (pH = 7.4): -1.6486077
• Log P: 1.4113084
• Molar Refractivity: 95.5844 cm^3
• Polarizability: 36.28805 Å^3
• Polar Surface Area: 107.53 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 295-297 °C
• Optical Rotation: [α]20/D +55±1°, c = 0.5% in 0.1 M NaOH

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C17H21N3O4S

DETAILS

Sigma Aldrich - 14408

Other Notes
Enzyme substrate used in the assay of biotinidase 1,2
Biochem/physiol Actions
Biotinyl-4-aminobenzoic acid (B-PABA) is used as a substrate in biotinidase assays.