16-(4-{[2-(methanesulfonylsulfanyl)ethyl]sulfamoyl}-2-sulfonatophenyl)-3-oxa-9λ5,23-diazaheptacyclo[17.7.1.15,9.02,17.04,15.023,27.013,28]octacosa-1(27),2(17),4,9(28),13,15,18-heptaen-9-ylium

• ChemBase ID: 154063
• Molecular Formular: C34H37N3O8S4
• Molecular Mass: 743.93288
• Monoisotopic Mass: 743.14634916
• SMILES: CS(=O)(=O)SCCNS(=O)(=O)c1ccc(c(c1)S(=O)(=O)[O-])C1=c2cc3c4=[N+](CCC3)CCCc4c2Oc2c1cc1c3c2CCCN3CCC1
• Canonical SMILES: CS(=O)(=O)SCCNS(=O)(=O)c1ccc(c(c1)S(=O)(=O)[O-])C1=c2cc3CCC[N+]4=c3c(c2Oc2c1cc1CCCN3c1c2CCC3)CCC4
• InChI: InChI=1S/C34H37N3O8S4/c1-47(38,39)46-17-12-35-48(40,41)23-10-11-24(29(20-23)49(42,43)44)30-27-18-21-6-2-13-36-15-4-8-25(31(21)36)33(27)45-34-26-9-5-16-37-14-3-7-22(32(26)37)19-28(30)34/h10-11,18-20,35H,2-9,12-17H2,1H3
• InChIKey: DHYGLLUUGIYOPV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 16-(4-{[2-(methanesulfonylsulfanyl)ethyl]sulfamoyl}-2-sulfonatophenyl)-3-oxa-9λ^5,23-diazaheptacyclo[17.7.1.1^5,^9.0^2,^1^7.0^4,^1^5.0^2^3,^2^7.0^1^3,^2^8]octacosa-1(27),2(17),4,9(28),13,15,18-heptaen-9-ylium
• IUPAC Traditional name: 16-(4-{[2-(methanesulfonylsulfanyl)ethyl]sulfamoyl}-2-sulfonatophenyl)-3-oxa-9λ^5,23-diazaheptacyclo[17.7.1.1^5,^9.0^2,^1^7.0^4,^1^5.0^2^3,^2^7.0^1^3,^2^8]octacosa-1(27),2(17),4,9(28),13,15,18-heptaen-9-ylium
• Synonyms: Texas Red®-2-sulfonamidoethyl methanethiosulfonate; TEXAS RED®-MTSEA; Texas Red®-2-sulfonamidoethyl methanethiosulfonate

Database IDs

• CAS Number: 386229-76-1
• PubChem SID: 162248202
• PubChem CID: 5014711

CALCULATED PROPERTIES

• Acid pKa: -2.0537407
• H Acceptors: 9
• H Donor: 1
• LogD (pH = 5.5): 1.6904616
• LogD (pH = 7.4): 1.6946747
• Log P: -0.7741172
• Molar Refractivity: 214.1532 cm^3
• Polarizability: 75.22457 Å^3
• Polar Surface Area: 152.99 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: Shiny Dark Burgandy Crystals
• Melting Point: >300°C
• Fluorescence: λex 588 nm; λem 609 nm in 0.1 M phosphate pH 7.0

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Moisture, Temperature Sensitive
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Suitability: suitable for fluorescence
• Empirical Formula (Hill Notation): C34H37N3O8S4

DETAILS

Sigma Aldrich - 44796

Analysis Note
degree of coupling ≥20%
Legal Information
Texas Red is a registered trademark of Life Technologies

Toronto Research Chemicals - T320200

A fluorescent compound used for the rapid and selective modification of sulfhydryl groups of enzymes. Fluorescence: max. Abs. 582nm; max. Em. 600nm; e x 10-3: 108

REFERENCES

• Yang, N. et al.: Neuron, 16, 113 (1996)
• Kuner, T. et al.: Neuron, 17, 343 (1996)
• Holmgren, M. et al: Neuropharmacology, 35, 797 (1996)
• Chahine, M. et al.: Biochemical & Biophysical Res. Commun., 233, 606 (1996)
• Ehrlich, B.E., et al.: J. Gen. Physiol.,