[9-(2-ethoxycarbonyl-phenyl)-6-ethylamino-2,7-dimethyl-xanthen-(3E)-ylidene]-ethyl-ammonium chloride

ID: ALA402140

Chembl Id: CHEMBL402140

Max Phase: Preclinical

Molecular Formula: C28H31ClN2O3

Molecular Weight: 442.56

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Rhodamine 6G

Canonical SMILES:  CC/N=c1\cc2oc3cc(NCC)c(C)cc3c(-c3ccccc3C(=O)OCC)c-2cc1C.Cl

Standard InChI:  InChI=1S/C28H30N2O3.ClH/c1-6-29-23-15-25-21(13-17(23)4)27(19-11-9-10-12-20(19)28(31)32-8-3)22-14-18(5)24(30-7-2)16-26(22)33-25;/h9-16,29H,6-8H2,1-5H3;1H/b30-24+;

Standard InChI Key:  VYXSBFYARXAAKO-WTKGSRSZSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 442.56

Molecular Weight (Monoisotopic): 442.2256

AlogP: 6.35

#Rotatable Bonds: 6

Polar Surface Area: 63.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.13

CX LogP: 5.35

CX LogD: 5.33

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.28

Np Likeness Score: -0.31

References

1. Cheng S, Clancy CJ, Nguyen KT, Clapp W, Nguyen MH..  (2007)  A Candida albicans petite mutant strain with uncoupled oxidative phosphorylation overexpresses MDR1 and has diminished susceptibility to fluconazole and voriconazole.,  51  (5): [PMID:17325226] [10.1128/aac.00182-07]

2. Yamane K, Wachino J, Suzuki S, Kimura K, Shibata N, Kato H, Shibayama K, Konda T, Arakawa Y..  (2007)  New plasmid-mediated fluoroquinolone efflux pump, QepA, found in an Escherichia coli clinical isolate.,  51  (9): [PMID:17548499] [10.1128/aac.00339-07]

3. Puri N, Prakash O, Manoharlal R, Sharma M, Ghosh I, Prasad R..  (2010)  Analysis of physico-chemical properties of substrates of ABC and MFS multidrug transporters of pathogenic Candida albicans.,  45  (11): [PMID:20739103] [10.1016/j.ejmech.2010.07.050]

4. Lamping E, Ranchod A, Nakamura K, Tyndall JD, Niimi K, Holmes AR, Niimi M, Cannon RD..  (2009)  Abc1p is a multidrug efflux transporter that tips the balance in favor of innate azole resistance in Candida krusei.,  53  (2): [PMID:19015352] [10.1128/aac.01095-08]

5. Tsao S, Rahkhoodaee F, Raymond M..  (2009)  Relative contributions of the Candida albicans ABC transporters Cdr1p and Cdr2p to clinical azole resistance.,  53  (4): [PMID:19223631] [10.1128/aac.00926-08]

6. Sharma M, Manoharlal R, Shukla S, Puri N, Prasad T, Ambudkar SV, Prasad R..  (2009)  Curcumin modulates efflux mediated by yeast ABC multidrug transporters and is synergistic with antifungals.,  53  (8): [PMID:19470507] [10.1128/aac.01497-08]

7. Nishino K, Hayashi-Nishino M, Yamaguchi A..  (2009)  H-NS modulates multidrug resistance of Salmonella enterica serovar Typhimurium by repressing multidrug efflux genes acrEF.,  53  (8): [PMID:19506059] [10.1128/aac.00371-09]

8. Long F, Rouquette-Loughlin C, Shafer WM, Yu EW..  (2008)  Functional cloning and characterization of the multidrug efflux pumps NorM from Neisseria gonorrhoeae and YdhE from Escherichia coli.,  52  (9): [PMID:18591276] [10.1128/aac.00475-08]

9. Saengkhae C, Loetchutinat C, Garnier-Suillerot A..  (2003)  Kinetic analysis of rhodamines efflux mediated by the multidrug resistance protein (MRP1).,  85  (1): [PMID:12944313] [10.1016/s0006-3495(03)74628-1]

10. Legentil L, Belaz S, Gangneux JP, Robert-Gangneux F, Ferrières V..  (2017)  Synthesis and biological properties of galactofuranosyl-containing fluorescent dyes.,  27  (2): [PMID:27956346] [10.1016/j.bmcl.2016.11.090]

Source

Source(2):

• Scientific Literature
• TP-search Transporter Database