Triphenyl(10-((3,4,5-trihydroxybenzoyl)oxy)-decyl)phosphonium Bromide

ID: ALA3234100

PubChem CID: 86276214

Max Phase: Preclinical

Molecular Formula: C35H40BrO5P

Molecular Weight: 571.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(OCCCCCCCCCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1)c1cc(O)c(O)c(O)c1.[Br-]

Standard InChI:  InChI=1S/C35H39O5P.BrH/c36-32-26-28(27-33(37)34(32)38)35(39)40-24-16-5-3-1-2-4-6-17-25-41(29-18-10-7-11-19-29,30-20-12-8-13-21-30)31-22-14-9-15-23-31;/h7-15,18-23,26-27H,1-6,16-17,24-25H2,(H2-,36,37,38,39);1H

Standard InChI Key:  KDIRFNXSUJACSS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 42 44  0  0  0  0  0  0  0  0999 V2000
   16.8917   -8.8351    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   17.2200   -8.1044    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.5051   -8.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7902   -8.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0753   -8.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3646   -8.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6497   -8.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9390   -8.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2241   -8.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5092   -8.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7944   -8.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0836   -8.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3687   -8.5162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6580   -8.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9432   -8.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9432   -9.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2283   -9.7521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5134   -9.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5134   -8.5162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2283   -8.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6580   -7.2805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8026   -8.1044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8026   -9.7521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2283  -10.5759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8081   -7.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9842   -7.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5722   -6.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9842   -5.9638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8081   -5.9638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2200   -6.6787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9308   -7.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9308   -6.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6456   -6.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3604   -6.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3604   -7.6925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6456   -8.1044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6319   -8.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4558   -8.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8677   -9.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4558  -10.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6319  -10.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2200   -9.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
 14 21  2  0
 19 22  1  0
 18 23  1  0
 17 24  1  0
 13 14  1  0
 12 13  1  0
  2  3  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 25 30  2  0
  2 25  1  0
 31 32  1  0
 32 33  2  0
 33 34  1  0
 34 35  2  0
 35 36  1  0
 31 36  2  0
  2 31  1  0
 37 38  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 37 42  2  0
  2 37  1  0
M  CHG  2   1  -1   2   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: 571.67

Molecular Weight (Monoisotopic): 571.2608

AlogP: 7.08

#Rotatable Bonds: 15

Polar Surface Area: 86.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.11

CX Basic pKa: ┄

CX LogP: 8.77

CX LogD: 8.69

Aromatic Rings: 4

Heavy Atoms: 41

QED Weighted: 0.06

Np Likeness Score: 0.28

References

1. Jara JA, Castro-Castillo V, Saavedra-Olavarría J, Peredo L, Pavanni M, Jaña F, Letelier ME, Parra E, Becker MI, Morello A, Kemmerling U, Maya JD, Ferreira J..  (2014)  Antiproliferative and uncoupling effects of delocalized, lipophilic, cationic gallic acid derivatives on cancer cell lines. Validation in vivo in singenic mice.,  57  (6): [PMID:24568614] [10.1021/jm500174v]

2. CatalAn, Mabel, Castro-Castillo, Vicente, Gajardo-de la Fuente, Javier, Aguilera, Jocelyn, Ferreira, Jorge, Ramires-Fernandez, Ricardo, Olmedo, Ivonne, Molina-Berrios, Alfredo, Palominos, Charlotte, Valencia, Marcelo, Dominguez, Marta, Souto, Jose A., Jara, Jose A..  (2020)  Continuous flow synthesis of lipophilic cations derived from benzoic acid as new cytotoxic chemical entities in human head and neck carcinoma cell lines,  11  (10): [PMID:33479625] [10.1039/d0md00153h]

Source

Source(1):

• Scientific Literature