2,5-dioxopyrrolidin-1-yl 4-[(19-{4-[(2,5-dioxopyrrolidin-1-yl)oxy]-4-oxobutoxy}-9,22-dioxoheptacyclo[13.11.1.12,10.03,8.016,21.023,27.014,28]octacosa-1,3,5,7,10,12,14(28),15(27),16,18,20,23,25-tridecaen-6-yl)oxy]butanoate

• ChemBase ID: 153186
• Molecular Formular: C44H32N2O12
• Molecular Mass: 780.73108
• Monoisotopic Mass: 780.19552447
• SMILES: c1cc2c3c(c1)C(=O)c1cc(ccc1c3c1cccc3c1c2c1ccc(cc1C3=O)OCCCC(=O)ON1C(=O)CCC1=O)OCCCC(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C(ON1C(=O)CCC1=O)CCCOc1ccc2c(c1)C(=O)c1c3c2c2cccc4c2c(c3ccc1)c1ccc(cc1C4=O)OCCCC(=O)ON1C(=O)CCC1=O
• InChI: InChI=1S/C44H32N2O12/c47-33-15-16-34(48)45(33)57-37(51)9-3-19-55-23-12-14-26-31(21-23)43(53)29-7-1-5-27-39-25-13-11-24(56-20-4-10-38(52)58-46-35(49)17-18-36(46)50)22-32(25)44(54)30-8-2-6-28(42(30)39)40(26)41(27)29/h1-2,5-8,11-14,21-22H,3-4,9-10,15-20H2
• InChIKey: CDBVPXLQWBQDPN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-dioxopyrrolidin-1-yl 4-[(19-{4-[(2,5-dioxopyrrolidin-1-yl)oxy]-4-oxobutoxy}-9,22-dioxoheptacyclo[13.11.1.1^2,^1^0.0^3,^8.0^1^6,^2^1.0^2^3,^2^7.0^1^4,^2^8]octacosa-1,3,5,7,10,12,14(28),15(27),16,18,20,23,25-tridecaen-6-yl)oxy]butanoate; 2,5-dioxopyrrolidin-1-yl 4-[(19-{4-[(2,5-dioxopyrrolidin-1-yl)oxy]-4-oxobutoxy}-9,22-dioxoheptacyclo[13.11.1.1^2,^1^0.0^3,^8.0^1^6,^2^1.0^2^3,^2^7.0^1^4,^2^8]octacosa-1(27),2(28),3,5,7,10,12,14,16,18,20,23,25-tridecaen-6-yl)oxy]butanoate
• IUPAC Traditional name: 2,5-dioxopyrrolidin-1-yl 4-[(19-{4-[(2,5-dioxopyrrolidin-1-yl)oxy]-4-oxobutoxy}-9,22-dioxoheptacyclo[13.11.1.1^2,^1^0.0^3,^8.0^1^6,^2^1.0^2^3,^2^7.0^1^4,^2^8]octacosa-1,3,5,7,10,12,14(28),15(27),16,18,20,23,25-tridecaen-6-yl)oxy]butanoate; 2,5-dioxopyrrolidin-1-yl 4-[(19-{4-[(2,5-dioxopyrrolidin-1-yl)oxy]-4-oxobutoxy}-9,22-dioxoheptacyclo[13.11.1.1^2,^1^0.0^3,^8.0^1^6,^2^1.0^2^3,^2^7.0^1^4,^2^8]octacosa-1(27),2(28),3,5,7,10,12,14,16,18,20,23,25-tridecaen-6-yl)oxy]butanoate
• Synonyms: Di(N-succinimidyl) 4,4′-[(8,16-dihydro-8,16-dioxodibenzo[a,j]perylene-2,10-diyl)dioxy]dibutyrate; 4,4′-[(8,16-Dihydro-8,16-dioxodibenzo[a,j]perylene-2,10-diyl)dioxy]dibutyric acid di(N-succinimidyl ester); 1,1'-[(8,16-Dihydro-8,16-dioxodibenzo[a,j]perylene-2,10-diyl)bis[oxy(1-oxo-4,1-butanediyl)oxy]]bis-2,5-pyrrolidinedione

Database IDs

• CAS Number: 243670-15-7
• MDL Number: MFCD07370106
• PubChem SID: 24873371; 162247325
• PubChem CID: 9853753

CALCULATED PROPERTIES

• Acid pKa: 17.408081
• H Acceptors: 10
• H Donor: 0
• LogD (pH = 5.5): 4.6500072
• LogD (pH = 7.4): 4.6500072
• Log P: 4.6500072
• Molar Refractivity: 203.3778 cm^3
• Polarizability: 83.34232 Å^3
• Polar Surface Area: 179.96 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 188-192 °C

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: ≥95.0% (CHN)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C44H32N2O12

DETAILS

Sigma Aldrich - 50512

Analysis Note
luminescence: Emax 668 nm (Exc.: 623 nm in chloroform)
Other Notes
Highly photostable, NIR fluorescent label (amine reactive) with larger Stokes shift than is usual for cyanine dyes and which is maximally excited (max CHCl3 620 nm) by He-Ne laser (630 nm) or diode laser (635 nm)1

Toronto Research Chemicals - D448885

Far-red dibenzo[a,j]perylene-8,16-dione dye derivative used as a fluorescent enzyme substrate and tags for biomolecules.

REFERENCES

• Deady, L. et al.: Synth. Comm, 20, 803 (2000)