N-(9-(5-(diethylcarbamoyl)thiophen-2-yl)-6-(dimethylamino)-3H-thioxanthen-3-ylidene)-N-methylmethanaminium hexafluorophosphate

ID: ALA493431

PubChem CID: 44139344

Max Phase: Preclinical

Molecular Formula: C26H30F6N3OPS2

Molecular Weight: 464.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)C(=O)c1ccc(-c2c3ccc(=[N+](C)C)cc-3sc3cc(N(C)C)ccc23)s1.F[P-](F)(F)(F)(F)F

Standard InChI:  InChI=1S/C26H30N3OS2.F6P/c1-7-29(8-2)26(30)22-14-13-21(31-22)25-19-11-9-17(27(3)4)15-23(19)32-24-16-18(28(5)6)10-12-20(24)25;1-7(2,3,4,5)6/h9-16H,7-8H2,1-6H3;/q+1;-1

Standard InChI Key:  ANGYJJIQWCSZAQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   11.8971  -16.0427    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.6070  -16.4646    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.3289  -16.0631    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.3407  -15.2402    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.6350  -14.8177    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   11.9132  -15.2189    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.6396  -18.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6384  -19.0362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.6710  -19.4363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9240  -19.4478    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2104  -19.0350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9234  -20.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4353  -16.4706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1013  -16.4779    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.8634  -15.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1948  -14.2761    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0442  -15.1218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7077  -13.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0402  -12.8564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0144  -14.1867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5016  -14.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  6  1  0
  1  5  1  0
  1  7  1  0
  1  3  1  0
  1  4  1  0
 23 25  1  0
 14 17  1  0
  9 26  1  0
 16 15  2  0
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 22 29  2  0
 12 11  2  0
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 18 19  1  0
  8  9  2  0
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M  CHG  2   1  -1  23   1
M  END

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: 464.68

Molecular Weight (Monoisotopic): 464.1825

AlogP: 5.31

#Rotatable Bonds: 5

Polar Surface Area: 26.56

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 3.29

CX LogP: 1.02

CX LogD: 1.02

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.30

Np Likeness Score: -0.92

References

1. Gannon MK, Holt JJ, Bennett SM, Wetzel BR, Loo TW, Bartlett MC, Clarke DM, Sawada GA, Higgins JW, Tombline G, Raub TJ, Detty MR..  (2009)  Rhodamine inhibitors of P-glycoprotein: an amide/thioamide "switch" for ATPase activity.,  52  (10): [PMID:19402665] [10.1021/jm900253g]

2. Orchard A, Schamerhorn GA, Calitree BD, Sawada GA, Loo TW, Claire Bartlett M, Clarke DM, Detty MR..  (2012)  Thiorhodamines containing amide and thioamide functionality as inhibitors of the ATP-binding cassette drug transporter P-glycoprotein (ABCB1).,  20  (14): [PMID:22727780] [10.1016/j.bmc.2012.05.075]

Source

Source(1):

• Scientific Literature