(10-(4-carboxy-3-hydroxyphenoxy)decyl)triphenylphosphonium bromide

ID: ALA4218451

PubChem CID: 145969622

Max Phase: Preclinical

Molecular Formula: C35H40BrO4P

Molecular Weight: 555.68

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C35H39O4P.BrH/c36-34-28-29(24-25-33(34)35(37)38)39-26-16-5-3-1-2-4-6-17-27-40(30-18-10-7-11-19-30,31-20-12-8-13-21-31)32-22-14-9-15-23-32;/h7-15,18-25,28H,1-6,16-17,26-27H2,(H-,36,37,38);1H

Standard InChI Key:  XMERLHVDQIEEBP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 41 43  0  0  0  0  0  0  0  0999 V2000
   13.4983   -5.9035    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   14.8590   -3.2267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8579   -4.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5726   -4.4669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2891   -4.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2862   -3.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5709   -2.8139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6818   -3.9207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6806   -4.7480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3955   -5.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -4.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1090   -3.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3936   -3.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3911   -2.6829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9672   -3.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9670   -2.6834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8270   -5.1589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5407   -4.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2558   -5.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9696   -4.7430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6847   -5.1544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3986   -4.7408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1136   -5.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8274   -4.7386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5425   -5.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2563   -4.7363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9714   -5.1477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6852   -4.7341    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.4003   -5.1454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6839   -3.9091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3997   -3.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3988   -2.6745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6832   -2.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9670   -2.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9715   -3.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3980   -5.9676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1123   -6.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8271   -5.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8232   -5.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1083   -4.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2529   -3.9210    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
 28 30  1  0
 28  3  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 30  1  0
 29 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 29  1  0
 15 41  1  0
M  CHG  2   1  -1  28   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: 555.68

Molecular Weight (Monoisotopic): 555.2659

AlogP: 7.58

#Rotatable Bonds: 16

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: 9.52

CX LogD: 6.06

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.11

Np Likeness Score: 0.07

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]

2. Manzano JI, Cueto-Díaz EJ, Olías-Molero AI, Perea A, Herraiz T, Torrado JJ, Alunda JM, Gamarro F, Dardonville C..  (2019)  Discovery and Pharmacological Studies of 4-Hydroxyphenyl-Derived Phosphonium Salts Active in a Mouse Model of Visceral Leishmaniasis.,  62  (23): [PMID:31702921] [10.1021/acs.jmedchem.9b00998]

Source

Source(1):

• Scientific Literature