D-Luciferin - 10mM in DMSO , CAS No.2591-17-5

CAS: 2591-17-5 Cat. No.: D422906 Formula: C₁₁H₈N₂O₃S₂ Peso molecolare: 280.32 Beilstein Registry Number: 27(4)8934 Numero EC: 219-981-3

GRADE & PURITY 10mM in DMSO

Synonyms

firefly luciferin (ketone tautomer) | L-8200 | 4-Thiazolecarboxylic acid, 4,5-dihydro-2-(6-hydroxy-2-benzothiazolyl)-, (S)- | BDBM50440036 | D-Luciferin, synthetic | EN300-99574 | 5TBB02N29K | Firefly luciferin | UNII-5TBB02N29K | s7763 | 3''-propionylleu

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Panoramica

D-luciferin is the natural substrate of luciferases that catalyze the production of light in bioluminescent insects.

Specifications

Sinonimi

firefly luciferin (ketone tautomer) | L-8200 | 4-Thiazolecarboxylic acid, 4,5-dihydro-2-(6-hydroxy-2-benzothiazolyl)-, (S)- | BDBM50440036 | D-Luciferin, synthetic | EN300-99574 | 5TBB02N29K | Firefly luciferin | UNII-5TBB02N29K | s7763 | 3''-propionylleu

Specifiche e purezza

10mM in DMSO

Meccanismi biochimici e fisiologici

Cell-permeable chemiluminescent luciferase substrate. Emits lights upon oxidative decarboxylation in the presence of ATP. Provides a bioluminescent signal for cellular ATP levels in vivo.

Condizioni di conservazione di stoccaggio

Store at -80°C

Spedito in

Dry ice packs + Cold packs

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Nomi e identificatori

• Pubchem Sid: 528764056
• Sorrisi canonici: C1C(N=C(S1)C2=NC3=C(S2)C=C(C=C3)O)C(=O)O
• IUPAC Name: (4S)-2-(6-hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid
• InChIKey: BJGNCJDXODQBOB-SSDOTTSWSA-N
• 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
• Isomeri SMILES: C1[C@@H](N=C(S1)C2=NC3=C(S2)C=C(C=C3)O)C(=O)O
• WGK Germania: 3
• Peso molecolare: 280.32
• Beilstein: 27(4)8934
• Reaxy-Rn: 269810
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=269810&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives
• Direct Parent: Alpha amino acids and derivatives
• Alternative Parents: Benzothiazoles 1-hydroxy-2-unsubstituted benzenoids Imidothiolactones Thiazolines Thiazoles Heteroaromatic compounds Propargyl-type 1,3-dipolar organic compounds Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Alpha-amino acid or derivatives - 1,3-benzothiazole - 1-hydroxy-2-unsubstituted benzenoid - Benzenoid - Imidothiolactone - Azole - Thiazole - Meta-thiazoline - Heteroaromatic compound - Carboxylic acid - Monocarboxylic acid or derivatives - Azacycle - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organoheterocyclic compound - Organooxygen compound - Organonitrogen compound - Organic oxide - Hydrocarbon derivative - Organic oxygen compound - Organopnictogen compound - Carbonyl group - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
• External Descriptors: benzothiazoles - 1,3-thiazolemonocarboxylic acid - imidothioate

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

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INSR Tclin Insulin receptor (5558 Activities)

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IGF1R Tclin Insulin-like growth factor I receptor (8605 Activities)

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MAPK11 Tchem MAP kinase p38 beta (2785 Activities)

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LCK Tclin Tyrosine-protein kinase LCK (9212 Activities)

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MAPK14 Tchem MAP kinase p38 alpha (12866 Activities)

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GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)

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PRKCZ Tchem Protein kinase C zeta (2414 Activities)

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MYLK Tchem Myosin light chain kinase, smooth muscle (1267 Activities)

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FGFR1 Tclin Fibroblast growth factor receptor 1 (9149 Activities)

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STK3 Tchem Serine/threonine-protein kinase MST2 (3069 Activities)

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CSNK1D Tchem Casein kinase I delta (4546 Activities)

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SRC Tclin Tyrosine-protein kinase SRC (10310 Activities)

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CHEK2 Tchem Serine/threonine-protein kinase Chk2 (4015 Activities)

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PDPK1 Tchem 3-phosphoinositide dependent protein kinase-1 (3758 Activities)

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AKT2 Tchem Serine/threonine-protein kinase AKT2 (4301 Activities)

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IKBKB Tchem Inhibitor of nuclear factor kappa B kinase beta subunit (5554 Activities)

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AURKB Tchem Serine/threonine-protein kinase Aurora-B (6805 Activities)

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PIM1 Tchem Serine/threonine-protein kinase PIM1 (9629 Activities)

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PKN2 Tchem Protein kinase N2 (1991 Activities)

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CSK Tchem Tyrosine-protein kinase CSK (2395 Activities)

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RPS6KA5 Tchem Ribosomal protein S6 kinase alpha 5 (3355 Activities)

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PRKD1 Tchem Protein kinase C mu (1904 Activities)

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SYK Tclin Tyrosine-protein kinase SYK (7372 Activities)

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PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)

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RPS6KA1 Tchem Ribosomal protein S6 kinase alpha 1 (2796 Activities)

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JAK2 Tclin Tyrosine-protein kinase JAK2 (12915 Activities)

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CAMK1 Tchem CaM kinase I alpha (1664 Activities)

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MAPK13 Tchem MAP kinase p38 delta (2605 Activities)

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MAPKAPK2 Tchem MAP kinase-activated protein kinase 2 (4814 Activities)

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MAPKAPK5 Tchem MAP kinase-activated protein kinase 5 (2831 Activities)

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ROCK2 Tclin Rho-associated protein kinase 2 (6206 Activities)

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MAPK9 Tchem c-Jun N-terminal kinase 2 (4655 Activities)

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MAPK10 Tchem c-Jun N-terminal kinase 3 (3396 Activities)

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MAP2K1 Tclin Dual specificity mitogen-activated protein kinase kinase 1 (4127 Activities)

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PRKCA Tchem Protein kinase C alpha (5923 Activities)

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MAPK3 Tchem MAP kinase ERK1 (4725 Activities)

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CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)

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MAP3K11 Tchem Mitogen-activated protein kinase kinase kinase 11 (808 Activities)

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NTRK1 Tclin Nerve growth factor receptor Trk-A (7922 Activities)

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DYRK1A Tchem Dual-specificity tyrosine-phosphorylation regulated kinase 1A (6484 Activities)

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MAPK8 Tchem c-Jun N-terminal kinase 1 (5038 Activities)

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RPS6KA3 Tchem Ribosomal protein S6 kinase alpha 3 (4284 Activities)

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RPS6KB1 Tchem Ribosomal protein S6 kinase 1 (4456 Activities)

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Mapk1 MAP kinase ERK2 (650 Activities)

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Meccanismi d'azione

Proprietà chimiche e fisiche

• Sensibilità: heat & light &air sensitive
• Rotazione specifica [α]: -33° (C=1,DMF)
• Punto di fusione (°C): 200°C
• Peso molecolare: 280.300 g/mol
• XLogP3: 2.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 279.998 Da
• Monoisotopic Mass: 279.998 Da
• Topological Polar Surface Area: 136.000 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 390.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1