(14-(3-Fluoro-4-(methoxycarbonyl)phenoxy)tetradecyl)triphenylphosphonium bromide

ID: ALA4209637

PubChem CID: 145966345

Max Phase: Preclinical

Molecular Formula: C39H47BrFO3P

Molecular Weight: 613.77

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C39H47FO3P.BrH/c1-42-39(41)37-29-28-33(32-38(37)40)43-30-20-9-7-5-3-2-4-6-8-10-21-31-44(34-22-14-11-15-23-34,35-24-16-12-17-25-35)36-26-18-13-19-27-36;/h11-19,22-29,32H,2-10,20-21,30-31H2,1H3;1H/q+1;/p-1

Standard InChI Key:  KIHJPQOGXMHRDO-UHFFFAOYSA-M

Molfile:  

     RDKit          2D

 45 47  0  0  0  0  0  0  0  0999 V2000
   26.7732   -7.4352    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   23.4516   -7.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4505   -8.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1652   -8.9063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8817   -8.4929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8789   -7.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1635   -7.2533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1151   -3.3749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1138   -4.2023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8287   -4.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5451   -4.2018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5422   -3.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8269   -2.9622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8244   -2.1372    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.4005   -2.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4003   -2.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2602   -4.6132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9740   -4.1996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6891   -4.6109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4030   -4.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1180   -4.6087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8319   -4.1951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5470   -4.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2608   -4.1928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9759   -4.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6897   -4.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4049   -4.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4061   -5.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6923   -5.8406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6936   -6.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9798   -7.0792    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.9811   -7.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2646   -6.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2639   -8.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2648   -9.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9805   -9.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6967   -9.1323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6922   -8.3095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2687   -5.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5543   -5.4316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8396   -5.8454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8435   -6.6746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5584   -7.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6861   -3.3753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9715   -2.9629    0.0000 C   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
 44 45  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: 613.77

Molecular Weight (Monoisotopic): 613.3241

AlogP: 9.28

#Rotatable Bonds: 19

Polar Surface Area: 35.53

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 2

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 11.00

CX LogD: 11.00

Aromatic Rings: 4

Heavy Atoms: 44

QED Weighted: 0.06

Np Likeness Score: -0.34

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