16-(2-carboxylato-4-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}phenyl)-3λ4-oxa-9,23-diazaheptacyclo[17.7.1.15,9.02,17.04,15.023,27.013,28]octacosa-1,3,5(28),13,15,17,19(27)-heptaen-3-ylium

• ChemBase ID: 155945
• Molecular Formular: C37H33N3O7
• Molecular Mass: 631.67382
• Monoisotopic Mass: 631.23185041
• SMILES: c1cc(c(cc1C(=O)ON1C(=O)CCC1=O)C(=O)[O-])c1c2cc3c4c(c2[o+]c2c1cc1c5c2CCCN5CCC1)CCCN4CCC3
• Canonical SMILES: O=C(c1ccc(c(c1)C(=O)[O-])c1c2cc3CCCN4c3c(c2[o+]c2c1cc1CCCN3c1c2CCC3)CCC4)ON1C(=O)CCC1=O
• InChI: InChI=1S/C37H33N3O7/c41-29-11-12-30(42)40(29)47-37(45)22-9-10-23(26(19-22)36(43)44)31-27-17-20-5-1-13-38-15-3-7-24(32(20)38)34(27)46-35-25-8-4-16-39-14-2-6-21(33(25)39)18-28(31)35/h9-10,17-19H,1-8,11-16H2
• InChIKey: BTTBJYLMDASSAS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 16-(2-carboxylato-4-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}phenyl)-3λ^4-oxa-9,23-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-1,3,5(28),13,15,17,19(27)-heptaen-3-ylium
• IUPAC Traditional name: 16-(2-carboxylato-4-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}phenyl)-3λ^4-oxa-9,23-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-1,3,5(28),13,15,17,19(27)-heptaen-3-ylium
• Synonyms: 5-Carboxy-X-rhodamine N-succinimidyl ester

Database IDs

• CAS Number: 209734-74-7
• MDL Number: MFCD07437880
• PubChem SID: 162250083
• PubChem CID: 2762608

CALCULATED PROPERTIES

• Acid pKa: 3.3889656
• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): 4.592295
• LogD (pH = 7.4): 3.2927594
• Log P: 6.5227213
• Molar Refractivity: 188.1531 cm^3
• Polarizability: 68.697845 Å^3
• Polar Surface Area: 123.43 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: acetonitrile: soluble; DMF: soluble
• Fluorescence: λex 575 nm; λem 600 nm in 0.1 M phosphate pH 7.0

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C37H33N3O7

DETAILS

Sigma Aldrich - 41969

Other Notes
Labeling reagent for prepn. of charge-modified dye-labeled ddNTPs to "direct-load" DNA sequencing1,2,3