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Rhodamine 123

Synopsis, Chemistry

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Also known as: 62669-70-9, 3,6-diamino-9-(2-(methoxycarbonyl)phenyl)xanthylium chloride, 3,6-diamino-9-[2-(methoxycarbonyl)phenyl]xanthylium chloride, Rh 123, Chebi:8828, Rh-123

Molecular Formula

C₂₁H₁₇ClN₂O₃

Molecular Weight

380.8 g/mol

InChI Key

MYFATKRONKHHQL-UHFFFAOYSA-N

A fluorescent probe with low toxicity which is a potent substrate for ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 and the bacterial multidrug efflux transporter. It is used to assess mitochondrial bioenergetics in living cells and to measure the efflux activity of ATP BINDING CASSETTE TRANSPORTER, SUBFAMILY B, MEMBER 1 in both normal and malignant cells. (Leukemia 1997;11(7):1124-30)

1 2D Structure

Rhodamine 123

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[6-amino-9-(2-methoxycarbonylphenyl)xanthen-3-ylidene]azanium;chloride

2.1.2 InChI

InChI=1S/C21H16N2O3.ClH/c1-25-21(24)15-5-3-2-4-14(15)20-16-8-6-12(22)10-18(16)26-19-11-13(23)7-9-17(19)20;/h2-11,22H,23H2,1H3;1H

2.1.3 InChI Key

MYFATKRONKHHQL-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COC(=O)C1=CC=CC=C1C2=C3C=CC(=[NH2+])C=C3OC4=C2C=CC(=C4)N.[Cl-]

2.2 Synonyms

2.2.1 Depositor-Supplied Synonyms

1. 62669-70-9

2. 3,6-diamino-9-(2-(methoxycarbonyl)phenyl)xanthylium Chloride

3. 3,6-diamino-9-[2-(methoxycarbonyl)phenyl]xanthylium Chloride

4. Rh 123

5. Chebi:8828

6. Rh-123

7. Rhodamin 123 Chloride

8. Schembl37743

9. Chembl245839

10. Schembl18816029

11. Dtxsid00886503

12. Amy40920

13. Hy-d0816

14. Akos015917525

15. Akos015958728

16. Cs-7693

17. R-22420rh-123

18. R-4500

19. R-22420

20. 2-(6-amino-3-imino-3h-xanthen-9-yl)benzoic Acid Methyl Ester

21. 3,6-diamino-9-(2-methoxycarbonyl-phenyl)-xanthenylium; Chloride

22. [6-amino-9-(2-methoxycarbonylphenyl)xanthen-3-ylidene]azanium;chloride

23. 6-amino-9-[2-(methoxycarbonyl)phenyl]-3h-xanthen-3-iminium Chloride

2.3 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₁₇ClN₂O₃
Molecular Weight	380.8 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Exact Mass	380.0927701 g/mol
Monoisotopic Mass	380.0927701 g/mol
Topological Polar Surface Area	87.1 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	670
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Fluorescent Dyes

Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags. (See all compounds classified as Fluorescent Dyes.)