(14-(4-carboxy-3-fluorophenoxy)tetradecyl)triphenylphosphonium bromide

ID: ALA4218131

PubChem CID: 145967521

Max Phase: Preclinical

Molecular Formula: C38H45BrFO3P

Molecular Weight: 599.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(OCCCCCCCCCCCCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1F.[Br-]

Standard InChI:  InChI=1S/C38H44FO3P.BrH/c39-37-31-32(27-28-36(37)38(40)41)42-29-19-8-6-4-2-1-3-5-7-9-20-30-43(33-21-13-10-14-22-33,34-23-15-11-16-24-34)35-25-17-12-18-26-35;/h10-18,21-28,31H,1-9,19-20,29-30H2;1H

Standard InChI Key:  UXRACSXODQIRNL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 44 46  0  0  0  0  0  0  0  0999 V2000
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   10.3736  -23.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0900  -22.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0872  -22.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3717  -21.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3234  -17.8286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3223  -18.6559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0370  -19.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7535  -18.6554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7506  -17.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0353  -17.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0328  -16.5908    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.6088  -17.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6086  -16.5913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3264  -19.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0402  -18.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7553  -19.0601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4691  -18.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1841  -19.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8980  -18.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6130  -19.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6143  -19.8805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9005  -20.2941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9018  -21.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1881  -21.5327    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.1893  -22.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4729  -21.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4722  -22.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4731  -23.5916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1888  -24.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9049  -23.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9005  -22.7630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4769  -20.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7626  -19.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0479  -20.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0518  -21.1281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7667  -21.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8945  -17.8289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 13 14  1  0
  8 15  1  0
 15 16  2  0
 11 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31  6  1  0
 32 34  2  0
 34 35  1  0
 35 36  2  0
 36 37  1  0
 37 38  2  0
 38 32  1  0
 33 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 42 43  2  0
 43 33  1  0
 15 44  1  0
M  CHG  2   1  -1  31   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: 599.75

Molecular Weight (Monoisotopic): 599.3085

AlogP: 9.19

#Rotatable Bonds: 19

Polar Surface Area: 46.53

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.61

CX Basic pKa: ┄

CX LogP: 10.65

CX LogD: 7.31

Aromatic Rings: 4

Heavy Atoms: 43

QED Weighted: 0.09

Np Likeness Score: -0.26

References

1. Meco-Navas A, Ebiloma GU, Martín-Domínguez A, Martínez-Benayas I, Cueto-Díaz EJ, Alhejely AS, Balogun EO, Saito M, Matsui M, Arai N, Shiba T, Harada S, de Koning HP, Dardonville C..  (2018)  SAR of 4-Alkoxybenzoic Acid Inhibitors of the Trypanosome Alternative Oxidase.,  9  (9): [PMID:30258542] [10.1021/acsmedchemlett.8b00282]

Source

Source(1):

• Scientific Literature