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

• ChemBase ID: 127425
• Molecular Formular: C11H8N2O3S2
• Molecular Mass: 280.32282
• Monoisotopic Mass: 279.99763413
• SMILES: O=C(O)[C@@H]1N=C(SC1)c1sc2cc(O)ccc2n1
• Canonical SMILES: OC(=O)[C@H]1CSC(=N1)c1nc2c(s1)cc(cc2)O
• InChI: InChI=1S/C11H8N2O3S2/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)/t7-/m1/s1
• InChIKey: BJGNCJDXODQBOB-SSDOTTSWSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 2591-17-5
• EC Number: 219-981-3
• MDL Number: MFCD00042929
• Beilstein Number: 30484
• PubChem SID: 24896524; 162221746; 24896428
• PubChem CID: 5484207
• Chemspider ID: 4588411
• Wikipedia Title: Firefly_luciferin

CALCULATED PROPERTIES

• Acid pKa: 3.5799313
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.32159984
• LogD (pH = 7.4): -1.1173017
• Log P: 2.2406247
• Molar Refractivity: 67.9257 cm^3
• Polarizability: 27.241076 Å^3
• Polar Surface Area: 82.78 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.742
• 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

• Purity: ≥99% (HPLC); 95%
• Biological Source: synthetic
• Quality Level: PREMIUM

DETAILS

Sigma Aldrich - L6152

Application
Substrate for firefly luciferase with a Km of approx 2 μM.
Linkage
Highly purified grade with reduced levels of inhibitor relative to L 9504

Sigma Aldrich - L9504

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