3,6-Bis(N,N-dimethylamino)-9-(2-thienyl-5-carboxamido)-thioxanthylium Hexafluorophosphate

ID: ALA524129

PubChem CID: 44139099

Max Phase: Preclinical

Molecular Formula: C22H22F6N3OPS2

Molecular Weight: 408.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1ccc2c(-c3ccc(C(N)=O)s3)c3ccc(=[N+](C)C)cc-3sc2c1.F[P-](F)(F)(F)(F)F

Standard InChI:  InChI=1S/C22H21N3OS2.F6P/c1-24(2)13-5-7-15-19(11-13)28-20-12-14(25(3)4)6-8-16(20)21(15)17-9-10-18(27-17)22(23)26;1-7(2,3,4,5)6/h5-12H,1-4H3,(H-,23,26);/q;-1/p+1

Standard InChI Key:  PMSRSYWOCDBLMO-UHFFFAOYSA-O

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
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    1.6311  -15.6190    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3404  -16.0405    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0615  -15.6395    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0733  -14.8173    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3370  -19.0208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1708  -16.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9117  -15.2690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1618  -16.0538    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3996  -14.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0685  -13.8541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2180  -14.6991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  6  1  0
  1  5  1  0
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  1  3  1  0
  1  4  1  0
 19 23  2  0
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  9 26  1  0
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 12 11  2  0
 16 17  1  0
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 17 18  2  0
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  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: 408.57

Molecular Weight (Monoisotopic): 408.1199

AlogP: 3.93

#Rotatable Bonds: 3

Polar Surface Area: 49.34

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.55

CX Basic pKa: 3.29

CX LogP: -0.14

CX LogD: -0.14

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.41

Np Likeness Score: -0.67

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]

Source

Source(1):

• Scientific Literature