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

ID: ALA4206705

PubChem CID: 145977413

Max Phase: Preclinical

Molecular Formula: C38H46BrO4P

Molecular Weight: 597.76

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc(OCCCCCCCCCCCCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1O.[Br-]

Standard InChI:  InChI=1S/C38H45O4P.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,(H-,39,40,41);1H

Standard InChI Key:  FKZQDVQPRXZZAI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 44 46  0  0  0  0  0  0  0  0999 V2000
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   10.2486  -14.8642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9650  -14.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9621  -13.6204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2468  -13.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1984   -9.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1973  -10.1603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9120  -10.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6285  -10.1598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6257   -9.3294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9102   -8.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9078   -8.0953    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4839   -8.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4837   -8.0957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.2014  -10.5668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9151  -10.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6303  -10.5645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3441  -10.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0592  -10.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7730  -10.1486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4880  -10.5600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4893  -11.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7755  -11.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7768  -12.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0630  -13.0372    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.0643  -13.8622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3479  -12.6258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3471  -14.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3482  -15.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0638  -15.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7800  -15.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7754  -14.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3519  -11.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6376  -11.3896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9229  -11.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9268  -12.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6417  -13.0401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7695   -9.3333    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: 597.76

Molecular Weight (Monoisotopic): 597.3128

AlogP: 8.75

#Rotatable Bonds: 19

Polar Surface Area: 66.76

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.08

CX Basic pKa: ┄

CX LogP: 10.85

CX LogD: 7.39

Aromatic Rings: 4

Heavy Atoms: 43

QED Weighted: 0.08

Np Likeness Score: 0.06

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