sodium (4S)-2-(6-hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylate

• ChemBase ID: 133054
• Molecular Formular: C11H7N2NaO3S2
• Molecular Mass: 302.30465
• Monoisotopic Mass: 301.97957838
• SMILES: c1cc2c(cc1O)sc(n2)C1=N[C@H](CS1)C(=O)[O-].[Na+]
• Canonical SMILES: [O-]C(=O)[C@H]1CSC(=N1)c1nc2c(s1)cc(cc2)O.[Na+]
• InChI: InChI=1S/C11H8N2O3S2.Na/c14-5-1-2-6-8(3-5)18-10(12-6)9-13-7(4-17-9)11(15)16;/h1-3,7,14H,4H2,(H,15,16);/q;+1/p-1/t7-;/m1./s1
• InChIKey: LILQLBIQROYWIA-OGFXRTJISA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4S)-2-(6-hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylate
• IUPAC Traditional name: sodium photinus luciferin(1-)
• Synonyms: (S)-2-(6-Hydroxy-2-benzothiazolyl)-2-thiazoline-4-carboxylic acid sodium salt; 4,5-Dihydro-2-(6-hydroxy-2-benzothiazolyl)-4-thiazolecarboxylic acid sodium salt; Firefly luciferin sodium salt; D-Luciferin sodium salt

Database IDs

• CAS Number: 103404-75-7
• MDL Number: MFCD00044938
• PubChem SID: 162227331; 24896446
• PubChem CID: 23710675

CALCULATED PROPERTIES

• Acid pKa: 3.5799313
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 0.32159984
• LogD (pH = 7.4): -1.1173017
• Log P: 2.2406247
• Molar Refractivity: 78.7628 cm^3
• Polarizability: 27.127092 Å^3
• Polar Surface Area: 85.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble
• Apperance: lyophilized powder
• Fluorescence: λex 328 nm; λem 532 nm in H2O

Safety Information

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

Product Information

• Biological Source: synthetic

DETAILS

Sigma Aldrich - L6882

Application
Substrate for firefly luciferase with a Km of approx 2 μM.