sodium 2-[(1E,3E,5E)-7-[(2E)-3,3-dimethyl-5-{[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamoyl}-1-(4-sulfonatobutyl)-2,3-dihydro-1H-indol-2-ylidene]hepta-1,3,5-trien-1-yl]-3,3-dimethyl-5-{[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamoyl}-1-(4-sulfonatobutyl)-3H-indol-1-ium

• ChemBase ID: 177708
• Molecular Formular: C49H69N4NaO18S2
• Molecular Mass: 1089.20793
• Monoisotopic Mass: 1088.39459767
• SMILES: c1cc(cc2c1[N+](=C(C2(C)C)/C=C/C=C/C=C/C=C/1\C(c2c(N1CCCCS(=O)(=O)[O-])ccc(c2)C(=O)NC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)(C)C)CCCCS(=O)(=O)[O-])C(=O)NC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[Na+]
• Canonical SMILES: OC[C@H]([C@H]([C@@H]([C@H](CNC(=O)c1ccc2c(c1)C(C)(C)/C(=C\C=C\C=C\C=C\C1=[N+](CCCCS(=O)(=O)[O-])c3c(C1(C)C)cc(cc3)C(=O)NC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)/N2CCCCS(=O)(=O)[O-])O)O)O)O.[Na+]
• InChI: InChI=1S/C49H70N4O18S2.Na/c1-48(2)32-24-30(46(64)50-26-36(56)42(60)44(62)38(58)28-54)16-18-34(32)52(20-10-12-22-72(66,67)68)40(48)14-8-6-5-7-9-15-41-49(3,4)33-25-31(17-19-35(33)53(41)21-11-13-23-73(69,70)71)47(65)51-27-37(57)43(61)45(63)39(59)29-55;/h5-9,14-19,24-25,36-39,42-45,54-63H,10-13,20-23,26-29H2,1-4H3,(H3-,50,51,64,65,66,67,68,69,70,71);/q;+1/p-1/t36-,37-,38+,39+,42+,43+,44+,45+;/m0./s1
• InChIKey: OBCDZDCGTDCFQV-MFZQRHOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 2-[(1E,3E,5E)-7-[(2E)-3,3-dimethyl-5-{[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamoyl}-1-(4-sulfonatobutyl)-2,3-dihydro-1H-indol-2-ylidene]hepta-1,3,5-trien-1-yl]-3,3-dimethyl-5-{[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamoyl}-1-(4-sulfonatobutyl)-3H-indol-1-ium
• IUPAC Traditional name: sodium 2-[(1E,3E,5E)-7-[(2E)-3,3-dimethyl-5-{[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamoyl}-1-(4-sulfonatobutyl)indol-2-ylidene]hepta-1,3,5-trien-1-yl]-3,3-dimethyl-5-{[(2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl]carbamoyl}-1-(4-sulfonatobutyl)indol-1-ium
• Synonyms: 1,1’-Bis-(4-sulfobutyl)-indotricarbocyanine-5,5’-dicarboxylic Acid Diglucamide Monosodium Salt; 1-Deoxy-1-[[[2-[7-[5-[[(1-deoxy-D-glucitol-1-yl)amino]carbonyl]-1,3-dihydro-3,3-dimethyl-1-(4-sulfobutyl)-2H-indol-2-ylidene]-1,3,5-heptatrien-1-yl]-3,3-dimethyl-1-(4-sulfobutyl)-3H-indolium-5-yl]carbonyl]amino]-D-glucitol Monosodium Salt; SIDAG Dye

Database IDs

• CAS Number: 308127-47-1
• PubChem SID: 164233618
• PubChem CID: 71752165

CALCULATED PROPERTIES

• Acid pKa: -1.184315
• H Acceptors: 19
• H Donor: 12
• LogD (pH = 5.5): -5.3469715
• LogD (pH = 7.4): -5.3474436
• Log P: -4.0683618
• Molar Refractivity: 284.2175 cm^3
• Polarizability: 105.23893 Å^3
• Polar Surface Area: 381.15 Å^2
• Rotatable Bonds: 28
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Dark Purple Solid
• Melting Point: 209-211°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - S422800

A carbocyanine-based dye for fluorescence optical imaging. It is a highly hydrophilic derivative based on a carbocyanine chromophore identical to ICG, and showing a low plasma binding of ~10%. It has an estimated blood half-life of ~200 min, is 60 times m

REFERENCES

• Meijer, D., et al.: Eur. J. Clin. Pharmacol., 35, 295 (1988)
• Less, J., et al.: Cancer Res., 52, 6371 (1988)
• Dawson, P., et al.: Eur. J. Radiol., 23, 172 (1988)
• Ebert, B., et al.: J. Biomed. Opt., 6, 134 (1988)
• Houston, J., et al.: Photochem. Photobio